Story In A Bottle Podcast (general)

When Bitcoin started gaining traction, Mike Dudas started buying. In fact, of all the cryptocurrencies out there, bitcoin is the only one he's gone all in on. But his passion for the Blockchain and Crypto world didn't end there. IN 2018, he not only put his money where is mouth was, but his whole career, when he started The Block, the goal being to create THE destination for news in the Blockchain and Crypto world. Over Negronis at Fools Gold in New York, Mike talks about how he started his career doing business development for Disney but eventually got the bug for FinTech, leaning to early roles at Google Wallet and Braintree, eventually co-founding the mobile payments company Button. Through it all, his devotion to crypto hasn't waned - including a passion so deep that it's gotten him kicked off Twitter multiple times. he talks about all that and more.


What You’ll Learn:

  • How you know it’s time to leave a company you founded
  • How using Twitter as a growth strategy can be a blessing and a curse
  • How to pivot your mission based on a quickly changing landscape
  • How to pivot your mission based on a quickly changing landscape
Direct download: SIAB_MDudas_v2.mp3
Category:general -- posted at: 1:04pm EST

The tech world is understandably frustrating and at some point, you’ve just had enough. For Katie Smith-Adair, that point came after she watched Sonar, the startup she was working for, blow up. The mobile app was part of a plethora of location-based people finding networks that permeated South by Southwest in 2012, but never really found its footing. Over a bottle of Chardonnay at Fools Gold in Manhattan, Katie talks about her experiences from waiting tables in Portland, Oregon to moving from the agency world to Microsoft and finally how she started PlaceInvaders, a culinary company that hosts unique dining events in amazing residential spaces.


What You’ll Learn:

  • How working in the service industry makes you better in the business world
  • The glory and fall of working for one of the hottest startups of the moment
  • The challenge and excitement of switching industries entirely to do what you love
Direct download: SIAB_KAdir_v2.mp3
Category:general -- posted at: 8:28pm EST

From music promotion to managing bars. From political strategist to startup founder. From consultant to professor. Jeremy Kagan’s gone down many roads over the course of his career. Over a variety bourbons at Fool’s Gold in New York, Jeremy talks about how his career has taken so many different turns, the emotional trauma of running your own startup and how all his experiences prepared him for his latest role as the Managing Director at the Eugene Lang Entrepreneurship Center at Columbia Business School.

What You’ll Learn:

  • How the challenges of the music industry make you smarter in the more traditional business world
  • How to persevere when your startup isn’t moving at the pace it needs for success
  • Why business school can actually be useful for an entrepreneur
Direct download: SIAB_JKagan_v3.mp3
Category:general -- posted at: 10:17am EST

Leah Finnegan’s journalism journey reads like the resume of someone decades in, which makes what she’s accomplished even more impressive. She first discovered her passion for journalism while working on the newspaper at the University of Texas and parlayed that into a stint at Columbia University’s Graduate School of Journalism, where she quickly realized that one does not need a master’s in journalism to be a good journalist. Over coffee and sparkling water, Leah shares how she’s worked her way up the journalism ladder from Gawker to the New York Times to the current Executive Editor of The Outline, the quirky online publication started by Josh Topolsky that recently sold to Bustle.


What You’ll Learn:

  • The challenges of going freelance
  • How to differentiate yourself as a media company
  • The value, or lack thereof, of a degree in journalism
  • How the media environment is changing in today’s political climate
Direct download: SIAB_LFinnegan_v1.mp3
Category:general -- posted at: 10:42am EST

Adam Levin has lead five different lives or at least had five different careers. From consumer protector to politician to real estate investor to digital entrepreneur to best selling author. And there’s even more beyond that. Over glasses of Lafroig scotch at Fool’s Gold in Manhattan, Adam sat down and discussed all of these facets of his life, including his experience shaping New Jersey’s consumer protection laws in the 1970s, why he co-founded, one of the biggest online financial services educators, in the 1990s, and what lead to his need to write Swiped, his book about protecting yourself from all forms identity theft.

  • How the government protects consumers from sketchy business practices
  • The things we don’t know about our own privacy
  • The history of cyber liability
  • The origin and exit of
Direct download: SIAB_ALevin_v1.mp3
Category:general -- posted at: 2:51pm EST

Growing up on the Hawaiian island of Kauai may not seem like a place where technology takes the forefront, but for Nicole Wilke it was a ubiquitous part of her life. Taking her lifelong education around design and computer science with her from the islands to the mainland, Nicole worked her way through media and tech’s biggest names. Over negronis  at Fool’s Gold in Manhattan, she talks about her experience at brands like Disney and Wired and the transition to her most recent role as Head of Product for Techcrunch.


What You’ll Learn:

  • The secrets behind what makes a good redesign
  • What it takes to break into media
  • Why a diverse skill set is critical to succeed in product design
Direct download: SIAB_NWilke_v2.mp3
Category:general -- posted at: 9:52pm EST

When Nick Carlson started at Business Insider, he was a young reporter coming off stints at Gawker Media and Internet News, putting his faith in a fledgling media startup. Today, he’s the Global editor in chief of BI and oversees 250 plus reporters and writers at the publication, which has become one of the biggest voices in tech journalism. Over Old Fashioneds at Fools Gold in New York City, Nick talks about how he went from working in world of finance at Merrill Lynch to becoming the go-to source for all things Yahoo with is book “Marissa Mayer and the Fight to Save Yahoo!” as well as what it means to spearhead a place that has become a tech and business new institution.

Direct download: SIAB_NCarlson_v2.mp3
Category:general -- posted at: 2:36pm EST

The genre of political and social journalism has spawned a plethora of new voices over the past few years and Taylor Lorenz has emerged as a notable voice, most recently as a staff writer for The Atlantic. Her origin story starts in New York City, where she grew up and as social media became a major destination for communication, she quickly adapted to it by becoming an early Tumblr user and building off that to eventually running social for The Daily Mail. Over bitters and soda at Fools Gold in New York City, Taylor talks about how she went from a social media expert to covering tech for Business insider and growing into her own as a journalist and finding her voice writing for The Hill and The Daily Beast.

Direct download: SIAB_TLorenz_v2.mp3
Category:general -- posted at: 7:46am EST

From a young age in New Zealand, Hamish McKenzie always had a passion for writing and he knew he was pretty good at it! He pursued an English degree and eventually earned a graduate degree in  journalism. Hamish went on to be a reporter and wrote for PandoDaily, the Guardian and the Toronto Star. His freelance writing eventually lead him to he role as head writer for the innovative car company, Tesla -- making Elon Musk his boss. Hamish used his experience in the  the day to day world of Tesla to write the book “Insane Mode: How Elon Musk’s Tesla Sparked an Electric Revolution to End the Age of Oil.” Today, he is the founder of Substack, a company that offers a newsletter business in a box that now powers subscription-based email content for independent writers and young media companies. Over KCBC Alewife Hash Cache IPA at Fool’s Gold in New York City, Hamish discusses getting into the world of journalism and how it brought him into corporate lifestyle, which eventually made him realize what world he truly wanted to be apart of.


What You’ll Learn:

  • Is journalism school worth it? 25:50
  • Should a publication like Gawker or PandoDaily make a comeback? 45:41
  • What is something about Elon Musk that nobody would read in the papers? 54:04
Direct download: SIAB_HMcKenzie_v2.mp3
Category:general -- posted at: 11:31pm EST

Erin Ryan grew up in a small town in Wisconsin and was always a big fish in a little pond. After earning a degree in English from Notre Dame, she began a career in finance, a path she quickly realized was not her destiny. And it was the Gawker Media run, woman-focusted site Jezebel that changed her life. An avid reader of it, she eventually started participating in the conversations there and, eventually, Jezebel asked her to contribute for real. Since then, she’s been all in as a writer, even parlaying her journalism talents into comedy writing, currently as a staff writer for “It’s Always Sunny in Philadelphia.” In addition to that new gig, which has brought her full time to Los Angeles, she also has a new podcast called “Hysteria,” produced by Crooked media and focused on women and politics. Over a fruity, fire-themed IPA at Fool’s Gold in Manhattan, Erin discusses how she grew up, how she became the great writer she is today and all the paths it took her to get there.


What You’ll Learn:

- What it was like growing up in a small town 6:15

- Why take the finance route in the first place? 44:00

- How Jezebel changed Erin’s life 47:36

- Experiencing a sitcom writer’s room for the first time. 1:01:00

Direct download: SIAB_ERyan_final.mp3
Category:general -- posted at: 11:59am EST

Lucas Arzola is a man with many different titles. He is an entrepreneur, educator, and innovation ecosystem builder. Originally from Puerto Rico, Lucas ventured to University of California, Davis for college and wound up staying to coordinate strategic partnerships between the university and pharmaceutical biotechnology companies. Lucas went on to found Betabox, a technology company that designs and delivers mobile spaces and on-demand experiences that enhance corporate innovation, workforce development, and STEM education . Today, back in his home country of Puerto Rico, he is the director of operations for the startup accelerator, Parallel18. Over a bottle of red wine at the Parallel18 offices in San Juan, Lucas discusses all his business ventures and how he spent his time dealing with the destructive aftermath of hurricane Maria and keeping his company based around technology and electricity afloat.


What You’ll Learn:

- Dealing with the growth of technology in other countries 11:40

- The challenges of Hurricane Maria 25:21

- Why go to California from Puerto Rico? 40:15

- Leaving your own company 1:05:24

Direct download: SIAB_LArzola_v2.mp3
Category:general -- posted at: 8:40am EST

Beth Schoenfeldt and Megan Hannum are experts at understanding the needs of startups. As business partners, they complement each other with Beth running the operations side of their company, FundedBuy, and Megan handling the networking. Together they are an unstoppable duo. At their core, Beth and Megan leverage their skills to ensure founders can focus on what it will take to get their founders to success and let the FundedBuy network handle all the ancillary day-to-day aspects of running a business. Over Graft Lost Tropic Cider at Fool’s Gold in Manhattan, this power (business) couple discuss their third party network, their individually unique backgrounds and how their unusual partnership came about.


What You’ll Learn:

  • What is FundedBuy? 1:20
  • How did two very opposite people become the business couple they are today? 12:33
  • How a startup is like a sitcom? 25:34
  • The key to having a smart startup and successful founders 40:02
Direct download: SIAB_FundedBy_v1.mp3
Category:general -- posted at: 1:40pm EST

Dave Malouf is a man who comes from many different career paths, but the one course he has stayed on through and through is the almighty Internet. He originally graduated from UC Berkeley with a degree in Anthropology, but he soon discovered he loved something else: web design. As Dave created new site after new site, he began to realize that he could help other users and other web designers come up with entire new strategies to this up and coming business. Thus was born The Interaction Design Association. AKA IxDA, an organization that is working to build a community of practice for the advancement and advocacy of the discipline of interaction design. Over Beak & Skiff Hard Cider at Fool’s Gold in Manhattan, Dave takes us on his journey as a pioneer in the Internet design world and how much has changed over time.

What You’ll Learn:

  • The major you graduated with in college might be more relevant than you think. (9:50)
  • Learning about technology as you go (25:19)
  • The evolution of interaction design (42:00)
  • Why interaction design is important (1:00:33)
Direct download: SIAB_DMalouf_final_v1.mp3
Category:general -- posted at: 7:44pm EST

At her core, Glynnis MacNicol has always known writing was her passion. She still remembers her first journal from when she was only 6 years old. Glynnis has translated that fierce need for independence into her role as the co-founder of TheList, a women only social network that seeks to bring professional women together for camaraderie, business connections and a space for open conversation. Glynnis loves to write about the intersection between media, pop culture, and politics. Her work has appeared in print and online for publications including Forbes, The Cut,, New York Daily News, Marie Claire, Capital New York, but also for publications like Fox News, MSNBC, NBC, and CBC. Over Bloody Mary’s at Fool’s Gold in Manhattan, she talks about her new memoir, No One Tells You This, about living through her 40th year, her colorful journey as a journalist in New York and how she struggled to learn the media world and how she continues to push what she can do in it.

What You’ll Learn:

- Culture of the modern day woman (its at the beginning)

- Was media a large part of Glynnis’ life as a kid (28:47)

- Why she wanted to be the voice (50:00)

Direct download: SIAB_GMacNicol_final.mp3
Category:general -- posted at: 11:48am EST

Ross Asdourian spends his day to day solving problems. According to him, that is one of the main qualities that makes a great producer. From starting as a freelance producer after college, to getting his first big break as the NBC News Creative Digital Product Manager, Ross paid his dues to get to where he is today, including roles as a Creative Director for NBCUniversal and a Producer for Red Bull. His second big break wasn’t quite as positive. To be blunt, Ross broke his penis. Over Knob Creek Rye at Fool’s Gold, he talks through his fascinating career journey and how one hook up lead to one of the most painful and hilarious experiences of his life, all documented in his book Broken Bananah.

What You’ll Learn:

- The life of a college mascot (7:23)
- Why producing is about problem solving (23:30)
- The exciting world of Red Bull (41:00)
- The story of the Broken Bananah (59:00)

Direct download: SIAB_RAsdourian_final.mp3
Category:general -- posted at: 11:29pm EST

Every choice you make in life can be a calculated decision. For Stephanie Vaughan, that is the way she let her career evolve. She was originally in the United States Marine Corp after attending the Naval Academy where she studied quantitative economics. Once her tour in Afghanistan was over, she went back to school where she received her MBA from Columbia Business School in order to further everything she already knew about finance and investment banking. She then pushed herself into the world of venture and now is Vice President of Block X Ventures. Over Sierra Nevada Kellerweis at Fool’s Gold in Manhattan, she shares with us how she went from navigating the challenges of a war to navigating the world of bitcoin and venture capital.


What You’ll Learn:

- What is Block X Ventures and the basics of investing in blockchain companies (1:44)

- Why study quantitative economics at the Naval Academy in the first place? (23:11)

- Is there a method to her madness? The plan to go from the Marines to finance (40:22)

Direct download: SIAB_SVaughn_final.mp3
Category:general -- posted at: 8:59am EST

Zach Mach’s original dream of working in the world of media has finally come to fruition, but not in the way he expected. Zach moved to New York right after he graduated college, in hopes of becoming a writer and even though he did have gigs at places like Gawker, he soon realized that a full time career in that world wasn’t his passion. His greater love in life was beer. And he has turned that into a career but opening ABC Beer Company on Avenue C in the Alphabet City and, now, as a writer covering the beer world for publications like Thrillist and GQ. Over local craft beers at ABC, he walks us on his journey of how he became a bar owner and what he has learned about running your own company...especially the unique aspects of bar life.

What You’ll Learn:

- What does it take to get involved in the bar owning business (3:50)

- The true experience of life in the bar world  (19:00)

- The deterrents to a career in writing and media (1:01:00)

Direct download: SIAB_ZMack_v3.mp3
Category:general -- posted at: 11:34am EST

When you start your career in a complicated industry and are able to realize how much experience you don’t have in order to do it well, that’s admirable. To actually gather that knowledge and then come back is exemplary; that is exactly what Melody Kohdid. After starting in venture capital after college, she didn’t think she was fit for the job just yet and wound up founding her own start up and, later, as head of product for Blue Apron. Now she is finally back to where she started, in VC, as a Venture Partner at NextView Ventures. Over Negronis at Fool’s Gold in Manhattan, she explains how each part of her career shaped who she is now and how it all prepared her for the dream career she would eventually have.

What You’ll Learn:

  • The NextView Ventures thesis Melody’s role on the team?
  • Running a business isn’t about you, so what/who is it about?
  • The best qualities for a founder/CEO
  • Why VC? And Melody found her way into technology.
Direct download: SIAB_MKoh_v3.mp3
Category:general -- posted at: 10:39am EST

When Chris Maddern discovered his passion for technology, he knew he was hooked. His addiction to it lead to a career that started with pioneering the early days of app development with his company AppLaunch, but quickly lead to a passion that has permeated his career since: solving the challenge of making transactions easier everywhere and anywhere. His work on Venmo revolutionized peer to peer payments and after that success he co-founded Button, which created a marketplace allowing publishers and merchants to make it easier for users to quickly buy, well, anything. Over Sidecars at Fool’s Gold in Manhattan, Chris discusses where his love of technology came from and how he translated that into a life.

What You’ll Learn:

  • What is Button and examples of where people would have used it? 4:12
  • How did Chris start up this kind of company? 7:40
  • Did Chris always want to be in the computer science world? 22:27
  • Inside perspective of what the early days of the app store was like 40:40
Direct download: SIAB_CMaddern_v3.mp3
Category:general -- posted at: 9:37am EST

Melanie Cristol has always let her passions drive her career. Those passions lead her to become a lawyer and, now, to become an entrepreneur. As a founder, she’s launched her most personal product yet: Lorals. Lorals are lingerie worn during oral sex, for when you love the idea of oral and you want to love the reality. This latex underwear will block anything you don't want transferred, whether it's an intimate view, menstrual or other fluids, or scents. And soon, Melanie hopes for Lorals to block STIs too. Over a shot of Maker’s Mark and some coffee on the side at Fool’s Gold in Manhattan, Melanie discusses her drastic career change and what it takes to create a new sex product line for women.


What You’ll Learn:

  • How do orgasms lead to physical benefits (4:40)
  • What does the name “Lorals” mean and what is their goal (6:50)
  • Types of products for oral sex that are already out on the market, so what makes Lorals different (8:00)
  • How did Melanie start this company and where did she get her inspiration (11:22)
  • What was Melanie’s approach in starting her company (24:53)
Direct download: SIAB_MCristol_v3.mp3
Category:general -- posted at: 8:33am EST

We all have a lost feeling after college life, even astrophysicists! Andrew Fleming originally went to Michigan Tech for physics and then took it one level higher to study astrophysics at Columbia University in New York. He realized before he was officially done with all school that the prospect of him spending the  rest of his days studying the stars and universe wasn’t in the cards if he didn’t commit himself to academia in perpetuity. So, he made a choice. Instead of the challenging and uncertain world of science and academia. He chose a totally different route: the challenging and uncertain world of media. . He went on to work as a content strategist and senior producer at Conde Nast and, later, VP of Product for Business Insider. Now, Andrew is the Head of Content Platforms at Dow Jones and the Wall Street Journal. Andrew loves his media world and wouldn't trade it for all the stars in the universe.


What You’ll Learn:

- What is “Moneyish” (7:40)
- How does a pop culture moment tie into these financial education moments (16:09)
- What drove him into the world of astrophysics? (26:17)
- How does product work and scientific research equate to each other? (41:57)
- The challenges of journeying from freelancer at Conde Nast to senior-level staffer at Business Insider when it was just starting out (55:40)

Direct download: SIAB_AFleming_v3.mp3
Category:general -- posted at: 1:43pm EST

Courtney Boyd Myers has always been a multitasking mover. She was born in Connecticut and grew up playing in multiple sports at one time, and in a family that moved around a lot. Both of those qualities has molded her into the person she is today. Courtney is the founder of AKUA, a company that creates sustainable, seagreens-based foods, an adviser of GreenWave, a nonprofit that supports the regenerative ocean farming industry, has invested in an ice cream store based out of Cape Town, South Africa called Unframed Ice Cream which focuses on the perfection of vegan ice cream, AND she is a Global Community Ambassador for the leadership event company, Summit. At just 33, she has accomplished so much in her life and continues to grow and love all of her personal and professional endeavors.


What You’ll Learn:

  • How did Courtney get started with her business, AKUA? (2:30)
  • When and where did media and tech businesses come into her life? (11:08)
  • How she got into the technology and startup world? (19:11)
  • Is mingling and being friendly in the journalism world a good thing? (21:00)
  • What a weekend through Summit is (34:35)
Direct download: SIAB_CBMeyers_v3.mp3
Category:general -- posted at: 9:59am EST

Daniel Kibblesmith grew up loving comedy and always found himself gravitating towards writing, but it took him awhile to realize he was actually writing comedy as a career. Starting off his career in Chicago after college, Daniel worked for Groupon as an in-house comedian and wrote humorous ad copy. This lead to him becoming one of the founding editors of ClickHole which eventually lead him to Buzzfeed in New York City and now as a staff writer for The Late Show with Stephen Colbert. Today, he is a published author with his book Santa’s Husband and just launched a comic book, Lockjaw, for Marvel. Daniel is doing what he loves everyday and happy to share his comedy with the world.

What You’ll Learn:

  • How does Daniel take in all the horrible events and news of each day and turn it into comedy on a deadline (24:20)
  • What made him get into comedy writing (27:00)
  • When your day is surrounded by comedy for a job, does it ever get overwhelming (50:00)
  • How to create a packet to become a tv writer (1:02:06)
  • What is the hardest parts of Daniel’s dream job (1:09:11)
Direct download: SIAB_DKibblesmith_v3.mp3
Category:general -- posted at: 6:44pm EST

The challenge of totally changing your career path after dedicating years to one industry is immense in and of itself. But to do it due to the emotional toll the first one took on you is at another level. Cheryl Wischhover started off her career as a pediatric oncology nurse for 15 years - seeing just how brutal the impact of cancer can be on a daily basis. Today, she is the Senior Beauty Reporter for the fashion and beauty online publication Racked. Cheryl always wanted to be a writer of some sort, but her family’s path turned her towards nursing. When she moved from Chicago to New York in the early 2000’s, she fell in love with fashion, blogging, and the rise of social media which quickly led her to a change that would reroute her entire life and finally let her live out her passions.


What You’ll Learn:

  • What is Racked and why is it different from writing for publications such as Glamour, Teen Vogue, and Elle (4:50)
  • The science behind writing about beauty and why Cheryl’s medical background has been a huge help to her (9:45)
  • How to be strong and follow your head and heart on what you really want to do in life (19:45)
  • Everything that prompted Cheryl to change her career and how she did it (31:00)
Direct download: SIAB_CWischhover_v3.mp3
Category:general -- posted at: 9:45pm EST

“Politics” should be John Knefel’s middle name. Growing up in a Iowa, a swing state, he understood the political world at a very young age, an that has stuck with him to today. At age 35, he has used his passion for politics as a throughline through the different careers he’s already had. Starting his career with stand-up comedy in New York right after college in the midwest, he parlayed that into his own podcast, Radio Dispatch, which lead him into the world of journalism,  freelancing for top publications like Rolling Stone and The Nation. With his newest venture, writing for Comedy Central's The President Show, he's finally been able to combine his two core passions: comedy and politics.


What You’ll Learn:

  • When writing for a political comedy show, how can you stick to satire rather than sticking to the daily news cycle (10:08)
  • Where is the line drawn for taking political comedy too far (17:25)
  • How to bring the trend of storytelling into comedy (47:00)
  • Why are people driven by their political beliefs (59:17)
  • How to make money as a freelance journalist in our day and age (1:13:48)
Direct download: SIAB_JKnefel_v3.mp3
Category:general -- posted at: 12:05am EST

Tennis has always been a passion for Caitlin Thompson, and now she is able to hone in on that passion with her own magazine, Racquet. From a young age, she knew being on the tennis court and telling stories were two things that just came natural to her. She continued those two natural feelings by playing tennis for the University of Missouri, which also happens to be one of the best journalism schools in the country. She went on to lead a very fulfilling life in journalism, writing for newspapers and magazines all over the world, and even though our world is shifting more to digital, nothing compares to the excitement and dedication to her own print magazine, and how she feels destiny has brought her two favorite worlds together into one.


What You’ll Learn:

  • Why Racquet is is so important for such a small community (5:10)
  • How money is valuable and media should not be free (28:54)
  • Why tennis has always been written on a spectrum of utility instead of about the people (30:37)
  • How Racquet is putting tennis players back into the cultural conversation (39:06)
Direct download: SIAB_CThompson_v3.mp3
Category:general -- posted at: 10:57am EST

Growing up in the Albanian community of New York, Ilir Sela was poised to continue the age-old tradition of owning and operating a local pizza shop. But simply following suit was not enough, and, as he grew and advanced in his technical skills, Ilir became the go-to in the community for all things IT related, starting with websites and online ordering, but later realizing the shifting needs of the industry, not only in New York, but nationally. It was this unique circumstance that equipped him to create a major platform to bring about the evolution needed to keep these local businesses connected with the communities they fed. As the founder of Slice, a digital ordering platform, he is constantly finding new ways to do this and to continue to ensure that this community staple finds it’s place in the future.

What You’ll Learn:

- Creative ways to garner interest in tech in an industry that has existed without it

- Why the local pizza shop industry deserves a different solution than big ordering platforms

Direct download: SIAB_ISela_v3.mp3
Category:general -- posted at: 11:51am EST

It goes without saying that the more connected we’ve become - the world, and the events reported around it, have changed; with information traveling the fastest it ever has, the role of storytellers has evolved and there’s nothing that stands in the way of telling the goings on from every which end. And still, while the world continues to get "smaller," it’s becoming continually challenging to know the happenings taking place in your own neighborhood. Kate Gardiner has spent her many years in and around the journalism world being a voice from an often unheard vantage point - whether it’s reporting in the isolated community of Molokaʻi or growing a network of professional women via - and even in her work today as founder of audience engagement firm, DSTL. Kate’s goal is simple: to build bigger and better communities and to connect them with the information they need to continue to grow.

What You'll Learn:

- The importance of getting the right story to the right audience

- How lack of innovation in local news has failed local audiences

- A tale of evolving entrepreneurship, beginning with exotic fish sales

Direct download: SIAB_KGardiner_v3.mp3
Category:general -- posted at: 3:33pm EST

It's safe to say that while the entertainment industry is so ingrained in our daily lives, it's inner workings and the lives of those in it are elusive to most. Over drinks at Fool’s Gold, Michael Cerveris gave us a glimpse behind the scenes including all of the exciting, high parts of his career: headlining a banner Broadway show, winning Tonys, making breakthroughs in television. However he also shared how in acting, much like other industries, even when you achieve a certain level of success, imposter syndrome is nearly impossible to avoid, and why he approaches each new project as way to start over again. And Again. And again.

What You'll Learn:

- How to maintain enthusiasm for a job even if it seems like you're doing the same thing over and over every day.

- Why "losing" can ultimately be better for your career.

- How imposter syndrome affects other industries.

Direct download: SIAB_MCeveris_v3.mp3
Category:general -- posted at: 2:00pm EST

Jennifer Wright began her career - with a passion and innate skill for writing - and during a time when content on the web was hitting critical mass, allowing personality and perspective to shine through unlike any time before. She boasts experience with publishing powerhouses like the New York Post, Cosmopolitan, and Glamour - as well as authored her own acclaimed books. We caught up with Jennifer at Fool’s Gold in New York City and over Snake Bite Violette’s she talks about how she got to where she is, what has inspired her writing thus far, and how the shift in our political atmosphere has ignited in her a new approach to her writing that she never expected.

What You’ll Learn:

- How to pursue a passion in writing without being defined by your “beat.”

- The new responsibility all journalists and content creators have in producing content and the necessity to consider global context

Direct download: SIAB_JWright_v3.mp3
Category:general -- posted at: 1:14pm EST

Ben Hill was a student not unlike many others; getting into school and choosing a path that seemed to make sense and not questioning why. It’d only make sense that when he graduated from Pitt with a degree in Communications he was left wondering what to do next. Over Teeling whisky at Fool’s Gold, Ben talks about the roundabout path he took to get to where he is today - the voice of an important aspect of Americana writing about Minor League Baseball - and the impetus for his blog “Ben’s Biz,” 12 years ago.

What You’ll Learn:

- How Minor League Baseball impacts American culture beyond the sport.

- What it’s like to create a new niche in journalism.

Direct download: SIAB_BHill_v3.mp3
Category:general -- posted at: 3:22pm EST

When Kristen Hawley set out to create her newsletter, Chefs + Tech, she had years of publishing and tech experience under her belt (spending time at Hearst, Pop Sugar, and Twitter in her early days). As such, as a founder, she always dreamt C+T would be part of a bigger editorial platform and, as of a year ago, that dream was becoming a reality. Joining us for the second time in the Charming Robot offices over Pinot Noirs, she fills us in on the last year of Chefs + Tech: being acquired by Skift and the challenges of a founder (and new mother!) in this position, how C+T has grown since joining the Skift ecosystem, and finally, to share the news of its latest iteration: Skift Table, which is officially launched at the Skift Forum in New York City last week.

What You’ll Learn:

How to start and evolve a product that you have large aspirations for.

The questions you should ask (and answer) as a founder with the prospect of being acquired.

How becoming a parent influences all of the above - and then some.

Direct download: SIAB_KHawley2.mp3
Category:general -- posted at: 11:06am EST

Anthony Batt, Co-Founder & Executive Vice President of VR company Wevr, obviously spends much of his time thinking about future innovations. However, it’s this curiosity that has been a driving force through much of his life and career - leading to the creation of products like Craigslist, Buzznet, and Thrash Lab, amongst others. Over La Croix Pure in his amazing office - former home to Dennis Hopper in Venice, CA - he explains his challenge of always thinking many steps ahead while waiting for technology to catch up and how this is especially true now in the lifecycle of VR.

What You’ll Learn:

- Why sometimes being first in the world of tech does not always guarantee your success.

- How solving a problem can lead to creating a product, even when you don’t mean to.

- The challenge of creating content and products that you know are too early for adoption - and the key decisions to make in this circumstance.

Direct download: SIAB_ABatt_v3.mp3
Category:general -- posted at: 12:22pm EST

Christina Heller is the Chief Development Officer of VR Playhouse, a creative production studio based in LA which is dedicated to creating great content for virtual reality experiences; a company she co-founded in 2014. It’s an industry she’s found by way of her love of storytelling, with a background in theater, political journalism radio, and documentary filmmaking. Over micheladas, Christina shares her thoughts on the budding industry, how it’s suffered because of unrealistic expectations set by those within it, the obstacles that still need to be overcome in order for it to reach mass adoption, and some of her great experiences creating content (which may or may not include a run in with one of her heroes, Ken Burns).  

What You’ll Learn:

  • Why VR is far from “dead.”
  • Insights into developing some of the first VR experiences for Time, amongst others.
  • The future of virtual experiences - and how you can eventually date without leaving the privacy of your own home.
Direct download: SIAB_CHeller_T2.mp3
Category:general -- posted at: 7:19pm EST

Ben Jackson has made a career in tech from figuring things out on his own. He got an early start with technology - tinkering around and teaching himself different coding languages - which lead to a series of IT jobs and the rest is history. Over beers at Fool's Gold in NYC we learned how those humble beginnings were just the start of a path in entrepreneurship, how he's evolved his role throughout, and eventually landing where he is today, helping fledgling companies make strategic decisions with his consultancy company For The Win.

What You’ll Learn:

- The challenges of evolving from print to digital at an agency in the early days of tech.

- An insiders perspective in starting a company abroad - and the circumstances that drive the decision to ultimately leave.

- Why company "politics" are important and shouldn't be considered a bad thing.

Direct download: SIAB_BJackson_v3.mp3
Category:general -- posted at: 12:35pm EST

As VC who invests in early stage companies - Adi Levanon of Symmetrical Ventures embraces the opportunity to help grow companies from the ground up. In fact, growing up in Silicon Valley with visionary-type parents, she was poised from an early age to enter the industry. However, she attributes a lot of her success to her time living in Israel, serving in the military, and later becoming a lawyer. Over mezcal margaritas at Fool’s Gold in New York City, Adi enumerates how “everything I’ve done has lead me to what I am doing now” - including sharing her daily experiences in her own podcast “The Adi Tells” podcast.

What You’ll Learn:

  • How to take a headstrong approach to entering a new field and finding a job in a new city.
  • Why learning you’re not a fit at a company is not a failure.
  • The value of working with investors who understand your industry.
  • Mistakes to avoid when you pitch.
Direct download: SIAB_ALevanon_v3.mp3
Category:general -- posted at: 9:10pm EST

Alexander Reyna is the Creative Director, Games and VR at MLB Advanced Media - whose primary role is to help bring to life the most innovative ways to put baseball content into the hands of its passionate fans. It’s a role that suits him well, as it intersects his entrepreneurial spirit and his design background, dreaming up big ideas and solutions as technology evolves. However, the road to get there was not without its perils. Over The Main Brewey’s Tiny Beautiful Something at Fool’s Gold he talks about the many failures and obstacles he overcame as an artist in his early career, his entry into tech from the gaming world, and how those experiences shape the work he’s doing today.

What You’ll Learn:

- How to take an entrepreneurial approach to the product design process

- Insights into how the tech and design industry has evolved

- Learning how to thrive beyond “failure”

Direct download: SIAB_ZReyna_v3.mp3
Category:general -- posted at: 2:13pm EST

Emily White is the co-founder of Dreamfuel and Whitesmith, two companies helping musicians and athletes achieve their goals. However, she began her professional career as a competitive swimmer. Born into a family of athletes, it only made sense that Emily attempt a stint in the pool but, when her interests deviated to the music world, she resourcefully used her competitive career as a springboard to get into the program of her choice at Northwestern. Over mocktails at Fool’s Gold in NYC, she describes her path through the music world - where she’s experienced almost every role in management from touring to talent - and how it’s lead her full circle back to swimming, as she contributes in a way she could’ve never envisioned.


What You’ll Learn:

- The important career lessons one can learn from jam bands.
- A woman’s perspective to the perils and biases encountered while fundraising.
- How understanding each part of your business is fundamental to being a strong leader.

Direct download: SIAB_EWhite_v3.mp3
Category:general -- posted at: 9:55am EST

Phillip Bowden has spent over the last decade entrenched in the world of tech; arguably the most evolutionary period in the industry’s history. What’s more, he’s experienced its growth from several key vantage points. From his earliest experience with computers - by way of tinkering around on a household PC he wasn’t supposed to - he essentially dove into the field in early development roles at Gowalla and Tumblr. However, when friction within the industry increased, he ultimately decided to do his own thing, co-founding consultancy Brooklyn Computer Club with Buzz Andersen. Over Penicillins, he explains the challenges of this ever-evolving industry and his shifting role within it, even today as he helps tech darling Spotify continue to grow.

What You'll Learn:

- Why having more people on a team doesn't ultimately solve a problem faster.

- The pros and cons of working in the tech field with little formal tech education.

- Insights into working for both early stage and larger companies - and the benefits of each.

Direct download: SIAB_PBowden_v3.mp3
Category:general -- posted at: 10:13am EST

When Jess Brown got her start with computers she spent her time designing for fun and trolling chat rooms online - seemingly a world away from a career in the then fledgling user experience industry. In fact, it was her love of math and the practical application of it at Stanford University that set her in motion. Over an Aperol Spritz, Jess tells us about those early days in a nascent industry, how she was able to guide her first gig with user research and why that lead her to join other startups like Threadflip and Rent the Runway. Today, she is Head of User Experience at Vice - applying the knowledge she’s gained along the way to this ever-expanding, content behemoth - which is no small task.


What You’ll Learn:

- Why test methodology matters in user research - and the importance of determining which is appropriate for understanding the specific user behavior you are testing.

- Why founders of companies may not necessarily need to be their end users and how that impacts design decisions.

Direct download: SIAB_JBrown_v3.mp3
Category:general -- posted at: 9:01pm EST

Khayyam Wakil boasts a career with an unbelieveable trajectory - all thanks his ability to identify and capitalize on trends. From Saskatoon, Saskatchewan, Canada, he rose to Twitter fame in the early 2000s, but what he didn’t know at the time was that his lighthearted exercise in gaming the platform would actually lead to true social influence. Over Malopas (mezcal palomas), he explains just how he became one of the 5% creating content on Twitter which lead to being one of the few selected to be a part of the UN’s envoy to curing malaria and how those experiences, in addition to his time in VR, have shaped his take on both activism and tech. This is especially important today, as he aims to bring more “first hand” experiences to the public in his latest endeavor as Head of Creative Partnerships at Live Planet.

What You’ll Learn:

  • The pros and cons of the “empathy machine” that is tech and Virtual Reality
  • Why sometimes having the propensity to learn is far more powerful than a linear path in education
  • The unfortunate truths about how social media has changed activism
Direct download: SIAB_KWakil_v3.mp3
Category:general -- posted at: 6:20am EST

Bianca Bosker is a journalist and nonfiction author whose body of work truly runs the gamut; from bowling to covering tech for HuffPo and spending a decade plus becoming an expert in Chinese “duplitecture” and beyond - it’s a career that appears to have no rhyme or reason. However, over Sage Beers at Fool’s Gold she helps explain the method to her madness - that, as a storyteller, she’s found true the old adage that “truth is stranger than fiction” and her obsessive nature helps her get to the heart of these truths. This is especially the case for her latest, bestselling book “Cork Dork” which chronicles her choice to drop everything and start at the bottom of the wine industry as “cellar rat” to endure the challenging path to certified sommelier.

What You’ll Learn:

- Behind the scenes of the early days of HuffPo’s tech coverage - and their thesis for differentiation

- The ins and outs of paving one’s way in the often elusive wine industry

Direct download: SIAB_BBosker_v3.mp3
Category:general -- posted at: 3:10am EST

In the startup community - from founders to investors to customers and employees - the first question that should be asked is “does this product solve a real problem?” Enter Preston Pesek, the founder of Spacious, a coworking company that aims to answer “yes” to solving not one, but two problems in major cities. Over Micheladas, Preston describes the painstaking process he took to identify and solve the problems of an ever-growing and displaced coworking crowd, as well as the vacancy of off-hours restaurants; with beta testing and shifting business models to transforming physical spaces - it’s a product that attempts to benefit all parties, and ultimately a story that shows how a real product process can lead to success.

What You’ll Learn:

- How to approach being a first-time founder

- The value of knowing what skills you possess and how to hire for those you don’t

- Understanding how to create a product that addresses a real problem vs. creating a problem to fit your product

Direct download: SIAB_PPesek_v3.mp3
Category:general -- posted at: 10:25am EST

Often times in our increasingly divided and contentious society, for better or worse, comedy is the only and best way to actually be heard. It’s something that Beth Newell and Sarah Pappalardo, co-founders of, know first hand. Dubbed the “the one and only fake women's news magazine” - through its satirical content -  Reductress aims to raise awareness of feminist issues. Over Bell’s Oberon Ale, Beth & Sarah talk about how it came to be and how their roles have evolved during its lifespan and the method to their madness of creating relevant content on a daily basis.

What You’ll Learn:

- Why, more than ever, fake news may be EXACTLY what we need to understand important issues

- Why being the “Oprah of satire” is the ultimate goal

Direct download: SIAB_Reductress_v3.mp3
Category:general -- posted at: 9:43pm EST

Sutian Dong, Partner at Female Founder’s Fund has spent much of her career in the Venture space - getting her start in Business School at NYU Stern and early experience at First Mark Capital thereafter. However, it’s a path that was not always so clearly defined for her. Over mezcal at Fool’s Gold, she explains her unique process of elimination in pursuing this direction, how it ended up getting her into venture during some of the key, formative years of startups and tech in NYC, and how it’s culminated to her unique position at Female Founders Fund today.

What You’ll Learn:

  • The experience of starting in VC when it was the “step cousin” to private equity and other, more “trendy” finance roles
  • What key things VCs want to hear from founders
  • Why diversity matters in company cultures and how it correlates with success
Direct download: SIAB_SDong_v3.mp3
Category:general -- posted at: 10:25pm EST

Jacob Lewis spent much of his early career in publishing - at the helm of the New Yorker and Conde Nast - during one of the most transitional times in the industry’s history. It was a vantage point that revealed a bird’s eye view of evolving processes and the eccentricities of staff - and ultimately the folly in flailing and dying publishing behemoths. It’s an experience that inspired him to do an about-face and embark on a company on his own - to pursue a path in tech. Over whisky (AND beer) at Fool’s Gold, he explains the challenges of establishing that first company, the lessons he’s learned along the way, and how he’s applying them to his latest endeavor - restaurant rating platform, Renzell.

What You'll Learn:

- A story of amazing career growth - from working in the mail room to executive levels.

- Behind-the-scenes insights about the challenges of evolving with tech in the publishing world.

- The importance of nuance of the service industry in reviews.

Direct download: SIAB_JLewis_v3.mp3
Category:general -- posted at: 5:27pm EST

With the major growth of the tech industry it’s never been easier to become a specialist; from hardware to software, design and development, bootcamps and formal degrees there are no shortage of avenues to take to lead you into your career. This is much different than the opportunities Brad Lauster had when his passion for technology began - as he worked his way from the ground up copying printed programs from Atari magazine. Over Sazeracs at Fool’s Gold in NYC, he shares his wealth of experience in both hardware and software, design and development roles spanning across companies like Intel, Stanford University, Equinox - as well as starting his own product, Bindo - all while making the web a better, more usable tool. This experience is especially important today, as he leads product design at Weight Watchers and helps to bring this aging company into a more engaging future.

What You'll Learn:

- What key characteristic all User Experience designers should have.

- The pros and cons of working for large companies.

- The first step to approaching a career in tech.

Direct download: SIAB_BLauster_v3.mp3
Category:general -- posted at: 12:03pm EST

Jo Piazza is an award-winning journalist and writer - known for her approach to covering the behind the scenes perspectives of the world’s most taboo or inaccessible topics. From fiction to non- she’s explored a lot of unchartered territory; the world of celebrity endorsements to the elusive lives of nuns and the leaders of a nascent tech industry, and most recently behind the closed doors of marriage. Over mocktails at Fool’s Gold in New York City, she explains how her passion for telling the stories that are not often told was a trajectory set when she was a curious kid growing up in Philadelphia - getting the scoop on locals at a neighborhood bar. It’s certainly a methodology we can raise a glass to.

What You’ll Learn:

- How Instagram is ruining marriage.

- The challenges of being a full time writer in 2017.

- How talking with people in bars can lead to a successful career.

Direct download: SIAB_JPiazza_v3.mp3
Category:general -- posted at: 1:02pm EST

As the tech industry has evolved there is one thing that has separated those who have been successful from those who were not - and that is their adaptability to change. This is a quality that Bart Mroz, CEO of SUMO Heavy Industries, has exuded nearly all his life - since the young age of 12 when he came to the US from Poland without being able to speak a word of English. Since then he has experienced myriad roles in tech - often bearing the burden of being the spearhead of a nascent discipline within older companies and continuing to evolve after he set his sights on a more the entrepreneurial path of running his own company.

What You’ll Learn:

  • The value in channeling a “you just gotta learn” attitude in uncertain moments of your life and career
  • How major loss can be beneficial to shaping the future of your business
  • A unique perspective of immigrating to the US and how that experience helped lead to a career of entrepreneurship
Direct download: SIAB_BMroz_v3.mp3
Category:general -- posted at: 9:56am EST

At the height of the information age, emphasis on education is also at an all-time high and conversations about the best approach and paths to success are in abundance. Sehreen Noor Ali, VP, Business Development at Kaplan, not only confronts this from a business perspective, but has been considering the multitude of options for many years. Over grapefruit spritzers, she recalls her personal path through formal education, with many years of post graduate studies and nontraditional, as she learned during her days at the State Department, and finally now, as a mom who is looking for the optimal environment for her daughter to thrive. It’s certainly not a one-size-fits-all model, which has benefit from her warrants consideration ensuring her continued success.

What You’ll Learn:

- How governments use social media to impact diplomacy

- The importance of understanding your learning style - finding the right way to maximize it

- How education has had to adapt in the world of digital

- Why you should worry about being well-rounded vs. well-educated

Direct download: SIAB_SAli_v3.mp3
Category:general -- posted at: 7:54am EST

When it comes to content - on the internet or otherwise - people usually fall predominantly into a category of “consumer” or “creator,” but can you be both? Alex Zalben’s passion for entertainment started at a young age - with a love of Monty Python that overshadowed his apprehension of public performing and a desire to write that catapulted him into a career of sketch comedy. However, over time and experience in both the comedy scene in NYC and professionally at Marvel, MTV and, he’s used his unique perspective to blur the lines and stay true to both aspects of his passion - a true appreciator (and self-proclaimed nerd) of the art he loves and a contributor who furthers the art himself.

Direct download: SIAB_AZalben_v3.mp3
Category:general -- posted at: 10:23am EST

Arikia Millikan is a journalist and entrepreneur with a resume that boasts digitizing traditionally print-centric brands. It’s a career that’s given her a fair share of behind-the-scenes experiences with the epidemic that’s overtaking the industry - the continued and steepening uphill battle of maintaining the right motivation in the world of news and content. Over Bloody Marys (with a fun twist) at Fools Gold in NYC, she explains how her unique approach in applying engineering principles paired with a “squeaky wheel” reputation help her press forward and innovate within this challenging space.

What You’ll Learn:

- The harm in not keeping balance in the separation between content and revenue in the world of publishing.

- Why it’s valuable to apply approaches from other disciplines when innovating and evolving media.

- How improved tools can make all the difference in quality content creation.

Direct download: SIAB_AMillikan_v3.mp3
Category:general -- posted at: 9:28am EST

If you’ve ever dreamed of your hobby becoming a career, Austin Smith’s story will resonate with you. Growing up in Des Moines, Iowa, Austin’s earliest interest was music, which led him to be the music director at his dad’s church at the ripe old age of 13. Going on to study music Washington University, technology was just a side interest that he didn’t know could be a career.

Over Zinfandel from Ridge Vineyards, Austin talks about the most formative experience of his career, how hacking his customer service job with technology helped him realize that maybe it was time to turn that side interest into a job, and how working on technology for The Observer and The Economist led him to form Alley Interactive with his business partner, Matt Johnson, to simplify life for the people creating journalism and to help people connect with the world around them.

What You’ll Learn:

- How going with your gut, being willing to figure it out as you go along, and partnering with the right people can lead to a great business.

- How working in a service job early on helps you relate to people throughout your career.

Direct download: SIAB_ASmith_v3.mp3
Category:general -- posted at: 8:46pm EST

Alex Leo is a news content and product development expert - with a resume that includes roles at ABC news, Reuters, and most recently as VP of Audience Development at the Daily Beast. And while there’s no shortage of great experience in the field, as it turns out, her education in the space began much earlier. Growing up with two writers as parents - her mom for Family Circle, amongst others, and her dad taking on conservative media - she began thinking about content at an early age. Over white wine spritzers at Fool’s Gold in New York City, Alex recalls her first steps into the industry, beginning with a traumatizing experience in visiting colleges with her parents, to pursuing english at Wesleyan University, and ultimately leading to her latest position - essentially a front row seat to observing the unprecedented and controversial marketing tactics used in the 2016 election cycle. She has a unique perspective that can only be forged by a lifelong relationship with the news - and one that has her poised for her next endeavor - starting her own thing to influence real change in the criminal justice realm.

What You’ll Learn:

- What “dark post” means and how it helped Trump win the election

- How to combine your professional skills with a personal passion to make a career move

- Why large media companies would do well if they adopted a startup approach to innovation and digital product development

Direct download: SIAB_ALeo_v3.mp3
Category:general -- posted at: 4:42pm EST

As technology has evolved, the distribution channels for audiences and consumption of content are at an all time high, the world of journalism is facing unprecedented pressure to “evolve or die.” This problem, however, is not new. It’s an ongoing struggle for balance that’s existed since news organizations appeared online over two decades ago. No one knows this more than Gabriel Snyder. As a writer in this pivotal time, he has been witness to the last decade plus of digital media evolution at major publishers like Gawker, Newsweek, the Observer, and the New Republic. Over rum old fashioneds provided by Fool’s Gold, he recalls that while each suffered from nuanced challenges, no publisher was spared and his insight to what he has seen and the lessons learned along the way are critical to understanding where the industry is headed.

Direct download: SIAB_GSnyder_v3.mp3
Category:general -- posted at: 10:31am EST

As both a journalist and digital strategist, with a background in social media marketing for large brands and a passion for politics, the stars seemed to align for Nisha Chittal during this past election cycle. Nisha helped lead major news organizations like NBC and MSNBC in their content production and distribution across emerging platforms and nontraditional channels like Facebook and SnapChat, which, of course, is not without many unique challenges. Over Aperol Spritzes at Fool’s Gold, Nisha describes how the newsroom organized itself in order to support these platforms, the shift in their approach after the widespread epidemic of “fake news,” and the importance of finding balance in a 24/7 news cycle world - including when it may be right to call it quits altogether.

What You’ll Learn:

  • How are publishers using social to tell the story in a different way.
  • The heightened responsibility of the journalism community to debunk and fact check their sources.
  • The incredible challenge to remain objective in a polarizing news cycle.
Direct download: SIAB_NChittal_v3.mp3
Category:general -- posted at: 4:54pm EST

As the dust settles on a historical election season and people continue to comb through all of the factors that lead to its results - one thing remains top of mind: the role of digital. Derek Parham, who acted as Deputy CTO of the Hillary Clinton campaign, offers some behind-the-scenes insights into the most internet-centric campaign to date; his integral role within the digital team which operated much like a well-funded startup. Over bourbon at Fool’s Gold in New York City he recounts his trajectory leading to this very unique role - starting with software development with his dad in the basement of his family’s Bedford, MA home to helping create Google’s suite of apps, to his startup trials and errors. It’s an experience that exemplifies tenacity and one that certainly gets our vote.

What You’ll Learn:

  • The value of learning all parts of the digital product process.
  • Why sometimes leaving a job without another lined up can be the best way to find the next opportunity.
  • The many unexpected pitfalls of tech-adoption within the political realm.
Direct download: SIAB_DParham_v3.mp3
Category:general -- posted at: 12:28am EST

As the world of journalism continues to evolve, so does the role of writers who exist within it. Enter Dana Schwartz. While her resume calls her an Arts and Entertainment writer for the Observer, that’s hardly encompassing of her “day job.” At 24, she has an impressive background; starting as a pre-med student at Brown before doing an about-face to pursue her passion in writing - and the many avenues it covers - including penning her first novel while interning at the Late Show, contributing to Mental Floss, and finding her balance with comedy and journalism as a “blue check mark” on Twitter. Over old fashioneds at Fool’s Gold in New York she describes her journey of falling head first into major media frenzies and taking the bold step of calling out her boss, and how it’s compelled her to continue to contribute and learn what her personal responsibility is along the way.

Direct download: SIAB_DSchwartz_v3.mp3
Category:general -- posted at: 9:57pm EST

Charles Adler embodies the true spirit of being a maker in the age of the internet - starting with the inception of an idea through prototyping, beta testing and ultimately launching and evolving as he goes. It’s a process he’s developed and perfected over the course of his career - with myriad roles including UX designer, visual designer, developer, founder, and more - in both on and offline companies. It’s this varied background and methodology that lead to his most popular endeavor yet as co-founder of crowdfunding site, Kickstarter, but over Bulleit Rye in WGN’s studio in Chicago, he explains how his background in the budding punk and EDM scenes and the self-starter culture that accompanied it not only lead to creating that platform, but has inspired him since. And that is still true today, as he approaches a new company - furthering facilitating the makers community in a more tangible way than ever before.

Direct download: SIAB_CAdler_v3.mp3
Category:general -- posted at: 10:47am EST

Sara Chipps is, first and foremost, a developer. At a very young age, growing up in New Jersey she was intrigued with the internet and all the possibility it held. As a student, she pursued coding with a passion - overcoming the hurdles that come along with being a woman in a field traditionally dominated by men. Her current startup, Jewelbots, which makes smart friendship bracelets that are designed to inspire girls to get more involved in coding, is the culmination of her experience and this early passion. Over sancerre provided by ABC Wine Co., Sara and I discuss her experience as a temp working a helpdesk, as the CTO of Flatiron school and founder of nonprofit Girl Develop It, that helped her form a company career that teaches people of all ages that not only does coding not have to be intimidating, but that it can be fun as well.

What You’ll Learn

  • How everyone can learn to code if they just give it a try
  • How getting involved in coding at a young age can open up opportunities
  • The key differences between being a CTO and a CEO
Direct download: SIAB_SChipps_v3.mp3
Category:general -- posted at: 11:48am EST

One of the themes of Story in a Bottle is that there’s no one path to a career in ___. Soren Bowie, a writer and editor at Cracked, is certainly the embodiment of that. While Soren was always interested in entertainment, his path to comedy writing was a winding one. From starting out as a child actor and star of some straight to DVD films, to getting paid to watch movies for a living as a DVD quality tester, to a few unintentionally unpaid writing assignments, to finally working his way into Cracked by making funny videos for eHow, Soren kept taking risks and following his interests. In a wide-ranging conversation over Moscow Mules, we talk about his path from rural Colorado to LA, the role of humor in explaining geopolitical drama, the trajectory of a joke on Twitter, why arguing with someone with opposing political views is never going to change their mind and, finally, why all the moms on 80s sitcoms were dead.

Direct download: SIAB_SBowie_v3.mp3
Category:general -- posted at: 9:44pm EST

Gizmodo Night Editor Eve Peyser always knew she wanted to be a writer. However, it was a chance encounter at a bar with a college friend paired with her talent for comedy that has landed her firmly at the intersection of journalism & comedy, especially as a powerful (and hilarious) voice on Twitter. Starting out as a sex and dating reporter, she would often mine her personal life for editorial content. As she has evolved personally, she’s pulled back on the self-professed over sharing and is using humor to delve into more serious topics such as mental illness, the current political climate, and the pitfalls of capitalism.

What You’ll Learn:

- A good scoop can come from anywhere - even Tinder!

- Why the responsibility of the media is more important than ever - even for those in non traditional, journalistic roles.

- The pros and cons of the over sharing culture on the internet.

Direct download: SIAB_EPeyser_v3.mp3
Category:general -- posted at: 11:18am EST

Author Robert Simonson always knew he wanted to be a writer, but even in his early career, never imagined where he ultimately ended up. Starting out as a theatre reporter in New York, but he grew tired of the beat and made a bold move into the world wine of wine to find more of a community. However, it was this change in trajectory, which corresponded with the cocktail revival in the US around 2006, that opened the door to his latest and lasting pursuit: the art and history of the cocktail. As one of the first reporters to cover this reviving scene, Robert saw an opportunity and became an expert, furthering his career as he authored The Old-Fashioned and A Proper Drink. Over Boulevardiers (Negronis with Rye instead of Gin) at Fools Gold Bar, Robert talks about the origins of the cocktail revival, how he educated himself when he wanted to change reporting beats, and how big liquor companies influence what we drink.

What you’ll learn:

- How and when to educate yourself to take advantage of an opportunity

- How knowing what you want to do early on can lead to a great career

- About the past, present, and future of the cocktail revival

Direct download: SIAB_RSimonson_v3.mp3
Category:general -- posted at: 3:57am EST

“We’re living in an era where companies can stand for something,” says Susan McPherson, founder of McPherson Strategies, a consultancy that connects brands and social good. Starting out as a journalist at USA Today, Susan’s road to entrepreneurship has been filled with unexpected twists and turns. With her dad’s words of “nothing is a prison sentence” in her head, Susan took risks, from changing the direction of her career from journalism to marketing to relocating from Washington DC to California and then Seattle. Over un-oaked South African white wine, she discusses how these risks set into motion the path to becoming an entrepreneur that she still follows today, as she opened up new markets and introduced new products at PR Newswire to the work she does today helping corporations create messaging and strategy through the lens of social good.
What You’ll Learn:

- How corporate social good programs can attract and retain the best customers and employees.

- How working as an “intrapreneur” in established companies can prepare you for entrepreneurship.

- How knowing your strengths and hiring great people to supplement your weaknesses can lead to success as an entrepreneur.

Direct download: SIAB_SMcPherson_v3.mp3
Category:general -- posted at: 9:55am EST

Merrill Brown has worn many hats over the course of his career in journalism; beginning at the Washington Post to founding editor-in-chief of, he’s seen first hand the evolution of the industry. From printing to mass distribution and the improvement of tools to help information spread faster, it’s never been an industry that benefit from resting on its laurels. Over beers at ABC Beer Co. in New York City, Merrill talks about how he’s kept this innate truth as motivation - and maintained a focus that’s one step ahead. This has served him especially well, as technology has made an ever-expanding world that much smaller and content production that much easier. Today, he’s poised to coach a new class of journalists to do the same, as the Director of the School of Communication and Media at Montclair State University where he helps to shape the future of the industry.

What You’ll Learn:

  • How and why a journalist’s responsibilities have increased over time
  • Why the industry may not be prepared for the short and long term of this political season
  • The danger in ignoring or rejecting trends in technology
Direct download: SIAB_MBrown_v3.mp3
Category:general -- posted at: 12:44am EST

One of the unfortunate, universal truths of humanity is that, at one point or another, everyone deals with the loss of a loved one. Be it a family member, close friend, spouse or partner, grief can manifest in many forms and stages, and so while it’s not novel in concept, it affects everyone completely differently. For Rebecca Soffer, the loss of both of her parents inspired her to seek company in others who have experienced the same, and was the catalyst that lead her to her co-founder, and ultimately their site Modern Loss. Over Shirley Temples, Rebecca talks about her path leading to that point - being the product of two parents who fostered her love of words, her unique background in Hispanic marketing (including several stints abroad), and how she eventually realized her dormant dream of going to Columbia Journalism School. And just when it seemed her resume was a bit winding, it was this distinct experience of loss that tied it all together to give her perspective. Modern Loss is as its name suggests: a community that embraces mourning and the unique circumstances created from it within the modern world, especially compared to the historical solution of trite, “this too shall pass” advice. Rebecca explains that, while all content on the site is singularly linked with the throughline of mortality, that it’s truly about the lives of the people who carry on, and how they have been impacted by their loss - happy, sad, confused or otherwise. And, while Modern Loss has been the solution to the problem she had personally needed to solve, becoming a founder has, of course, lead to more challenges as she grows and expands the site to help create that haven for others.

What You’ll Learn:

  • How to create a content site where you may be part of the audience, but not the only audience.
  • The value of taking comfort where it provides itself - even if it is not your perspective.
  • Why being a successful founder takes a healthy combination of “balls and ignorance” (at least, according to her dad).
Direct download: SIAB_RSoffer_v3.mp3
Category:general -- posted at: 1:20am EST

A natural entrepreneur is someone who, despite his best effort, can only excel in business when he works for himself. However, when he can also focus that drive with the clear vision to see opportunity where others do not, he’s passed litmus test as a true innovator. Tony Mugavero is just that. As co-founder and CEO of Virtual Reality platform Littlstar, Tony and his team come up with innovative ways to bring virtual reality to the masses; from 360-degree, journalistic videos to immersive, branded content, across myriad devices, they are leading the charge in this seemingly nascent industry. Over Victoria Prima Pilsners provided by ABC Beer Co., Tony talks about not only his path leading to this industry - by way of small businesses since he was a kid growing up in Dallas to his experience creating a music streaming service in the mid-2000s - but also the growth of virtual reality since its inception. Though it’s one of the hottest, up-and-coming trends in the tech world today, which is just now getting to some of the peak experiences at consumer level, he reminds us that VR has been around for decades and gives insight about how we can expect the best experiences ahead of us.

What You’ll Learn:

- How to not only make it, but pioneer an industry where you have little to no experience

- Behind the scenes in virtual reality content distribution

- The challenges in trying to work with Lucas Films and Star Wars

Direct download: SIAB_TMugavero_v3.mp3
Category:general -- posted at: 12:28am EST

One of the most valuable characteristics an entrepreneur can possess is having a well-rounded background of roles and perspectives over the course of his or her career - establishing a baseline of context and experiences to better serve in business pursuits. It’s a quality that is not lost on Jenna Matecki, founder of Matecki & Co. When considering her path, on the surface, it seems obvious that she is driven by the pursuit of her passions, sharing equal time between politics and art while layering in tech and startup experiences, as well. Over negronis, we learned what’s truly at the heart of her drive: her natural tendency to uncover the most interesting aspects that define the story, and, while the subject matter may change, it’s this role as a modern historian which remains constant. That is especially apparent today, as founder of Matecki & Co., where she sits poised at the intersection of brand, PR, and marketing - helping companies large and small define the elements of their DNA and, ultimately, their story. And as a personal project - leads her to uncovering the stories of others, which she showcases on her podcast ‘Notes On Doing’ (which may or may not have a familiar guest this week).

What You’ll Learn:

- As a company - the value of expressing what is special and unique about what you do.
How to put an interesting lens on what otherwise might be considered banal
- Why straying away from societal norms can be important to your or your company’s success

Direct download: SIAB_JMatecki_v4.mp3
Category:general -- posted at: 2:51am EST

As technology continues to evolve and consumer habits shift so do trends in content creation in order to reach people in myriad ways. And while there is no end in sight, Will Mayo, founder of Spoken Layer is doubling down on sound. Growing up with dyslexia and overcoming the challenges that came along with it as a student, Will has not only appreciated this medium, but thrived because of it - benefitting from having his textbooks audio-translated. Moreover, in having a musical inclination and passion for choral singing, this interest was only further substantiated. Over ginger beers he explains how the culmination of these things plus his academic career in engineering lead to the first iteration of Spoken Layer - with a goal of being a music collaboration tool. However, like any great founder, he was able to listen to the needs of his audience and, while learning how to operate at various life stages of his company, he was also able to pivot (twice) in order to finally realize the true problem audio was able to solve. Today, as the company has grown to fit into the more compartmentalized consumption habits of the population - as an audio-transcription of some of the most popular content on the internet - Will too is figuring out how this fits into his day-to-day as a founder and thought leader in the space.

What You’ll Learn:

- How to transform a space to adhere to meditation, work, and life

- The benefit of test and learn approaches to product development

- The importance of managing your expectation of employees based on your company’s life stage

Direct download: SIAB_WMayo_v3.mp3
Category:general -- posted at: 12:54am EST

Gillian Morris, founder of travel app Hitlist, has a story that is unsurprisingly filled with travel; from family trips to Canada as a kid, a stint living in a bell tower in Paris, and journalist gig in Turkey, she’s certainly appreciated many points of view across the globe. That’s how she became the unordained travel agent of her immediate friends and family, and despite her initial tech ineptitudes, was uniquely poised to bring these types of opportunities to the market. Over ginger beer and vodkas, we get a behind the scenes peek at the milestone moments that have lead her to where she is today; with a resume that includes a Harvard degree, international journalism experience with CNN, and even parakeet wholesaling (yes, that’s right). Gillian explains how the single driving motivator has always been to set her sights on a new place and see what happens and how she’s able to continue to achieve that today, even with a founder’s schedule keeping her mostly grounded.

What You’ll Learn:

  • The myriad trials-and-errors of fundraising
  • How it’s possible to turn your passion into a business
  • The benefit of changing your perspective - and the impact it can have on your career
Direct download: SIAB_GMorris_v3.mp3
Category:general -- posted at: 8:25pm EST

A strong investment thesis can help VCs sift through the plethora of companies that come their way. With Primary Ventures, Brad Svrluga’s second venture firm, he’s focused on companies that are solving real problems with SAAS products for both businesses and the general public. Over Mezcal, Brad talks about his path to venture after shortly considering a career in chemistry, his quick shot up and even faster fall down in the venture world of the dot-com boom, and what it takes to get in front of him and his partner to pitch your startup.

What You’ll Learn:

  • The challenges in building product and distinguishing between what the market thinks they want vs. what the market needs
  • Why investing in a great idea and an authentic founder without a clear business plan is okay
  • How the way startups approach funding is can be an example of how they run their companies
Direct download: SIAB_BSvrluga_v3.mp3
Category:general -- posted at: 8:30am EST

Caitlin Strandberg has a resume that spans many industries and roles -- from studying history in undergrad and a MBA from Harvard post-grad, to a stint in content creation and publishing in the music world, to hands-on founder apprenticeship at noteworthy startup, Behance — she’s appreciated many perspectives. However, over Arnold Salazars (an homage to her hometown in Florida that she shares with pro golfer Arnold Palmer) she explains that her drive is that of the eternal student - that once she overcomes a steep learning curve of one industry, she’s searching onward to the next. That path has served her well, and especially today, as a “student" of Venture at Firstmark Capital, where she brings her unique background to the table while she embarks on the path to becoming the next best investor.

What You’ll Learn:

- The value of having a great mentor

- How sometimes making a career out of your passion may not be the best move

- The benefit of being a “student” in your career - and how to approach new opportunities

Direct download: SIAB_CStrandberg_v3.mp3
Category:general -- posted at: 12:40am EST

In the high risk world of venture capital, investors need to not only be savvy, but also innovative. Charlie O’Donnell stands out in the crowd as one such VC whose process is nothing less than unorthodox. The native New Yorker and sole partner of Brooklyn Bridge Ventures sets his own rules - taking meetings literally anywhere with anyone, resulting in one of the most diverse portfolios (including an incredibly diverse stable of founders) to-date. Over homemade milkshakes from one of his investments, Ample Hills Ice Cream, he talks about how this diversity is important for early stage investors specifically, but not without the challenges of growing into this position of power and the scrutiny that comes along with it.

What You’ll Learn:

  1. How to learn and grow from criticism and setbacks, especially when they are public
  2. How to find and deliver value in every meeting
  3. Why it’s important to know your expertise - and when to call on others who know more than you
Direct download: SIAB_CODonnell_v3.mp3
Category:general -- posted at: 11:45pm EST

Bianca Caampued, one of two small girls who founded the aptly named Small Girls PR, began her career under the equally appropriate internet pseudonym BiancaRocksOut. In those early days, she rocked out in every aspect of her life, from running PR for Cure, a thrift store in New York City to seeking out the unique opportunities of the social and tech landscape that the city afforded. The circumstance was primed such that when she connected with her co-founder, whose birthday party she crashed, they found they shared a desire to create content and an entrepreneurial spirit that lead them to create Small Girls PR. Over glasses of Pedialyte (there’s an explanation, we promise), she shares how their interest in creating a web series lead to the founding of their PR company and how they’ve figured it all out along the way. Now, several years, incredible clients and projects in, the company has grown well beyond its initial expectation, boasting a staff of 40+ spanning both coasts (and more than small girls, at that), but is still rocking out… maybe in a slightly different way.

What You’ll Learn:

- Whether or not a formal business plan is necessary when starting a company

- The value of culture and a personal brand within your company

- The perspective of starting a company with social media at its core

Direct download: SIAB_BCaampued_V3.mp3
Category:general -- posted at: 3:00pm EST

If there are two sides to every story, it seems that at the speed in which information travels these days, and the multitude of sources, perspectives are, more than ever, in great conflict. Enter Michael Cervieri. Michael has always known he was meant to be a Writer (with a capital “W”), and, while he spent his early days pursuing the life of a great novelist, he has consistently chosen to entrench himself in perspective and presented his work accordingly. However, when his travels in Central America lead him to deviate from fiction down a path of adventure journalism he was able to see most clearly where that perspective was most desperately needed. Over negronis, Michael talks about how this awareness lead him back to journalism school on the heels of 9/11 and a stint in the Middle East thereafter, and how it’s all culminated at his current project - the Future Journalism Project. His mission has never been more clear; the news cycle demands a rewrite and while the interconnectedness of social has given us the ability to share information at a rapid pace, not all news warrants that protocol.


What You’ll Learn:

  • How every company is a media company.
  • Why discerning the importance of news events is an ongoing challenge for the public - “When everything has this heightened importance, nothing really has heightened importance.”
  • The difference between the practice and academics of journalism.
Direct download: SIAB_MCervieri_v3.mp3
Category:general -- posted at: 5:50pm EST

Renee DiResta's career has been far from conventional; from a government gig to programmer-turned-trader on Wall Street to a stint as a VC in Silicon Valley, she's certainly appreciated many points of view. Today, as the Founder and Director of Marketing of Haven, a shipping container marketplace catering to myriad clientele, that varied experience has proven to be helpful as she navigates the complicated world of a startup - especially one trying to innovate and bring a centuries old industry into the world of digital. Over virgin mimosas (orange juice and seltzer) she explains how she's had to evolve her working style from industry to industry, the importance of empathy when building both products and teams, the logistics of logistics and the many challenges of revolutionizing one of the the world’s first industries.

What You’ll Learn:

  • As a startup, how to avoid building something nobody wants (hint: it starts with company leadership)
  • Why a product should aim to “enable” rather than “disrupt”
  • How to succeed in an industry even if you’re not a subject matter expert
Direct download: SIAB_RDiResta_v3.mp3
Category:general -- posted at: 9:21pm EST

In the world of User Experience, the argument of formal education vs. on the job training is bigger than ever. One could argue that Tomer Sharon began his education in User Experience long before the field even existed. As a young man serving seven years in the Israeli Defense Forces, and as a project manager at a defense contractor after, he was immersed in training in problem solving and complex systems and the use of technology in critical circumstances. However, what his service left him longing for was bringing creativity into his day to day vernacular, which finding, was less clear. After several attempts at school and work - from copywriting to advertising gigs - he eventually found a path officially into User Experience; a world he understood long before he arrived. Since then, he’s spent the better part of his professional life at Google where he helped inform many products, most recently gathering insights impacting search results - a system that, while simple to the user, is solely so because of the careful consideration of the team. Today, as Head of UX at WeWork, he has taken his immense knowledge of complex systems and user research to bridge the customer experience both on and offline. Over Sam Adams he tells us about his approach to resolving the issues of this growing company and why, while largely unavailable to him, formal education is at the top of his checklist for potential User Experience candidates.

What You’ll Learn:

  • The importance of a discerning mind in user research - why all insights shouldn’t be taken at face value.
  • How becoming your audience may be the key to understanding your product.
  • Behind the scenes of Google’s hiring process and why it takes so long
Direct download: SIAB_TSharon_v3.mp3
Category:general -- posted at: 2:46pm EST

Drew Grant has spent the better part of her professional career at the forefront pop culture; from her early days as an editorial assistant at to establishing one of Observer’s most successful verticals, it’s a niche subject matter where her personal interest and voice thrive. Over hard root beers provided by ABC Wine Company, she recalls some of the more exciting moments of her career: from her early childhood inspiration that got her interested in entertainment news (spoiler: it has to do with Jurassic Park) and how it ultimately paid off, meeting President Obama (twice!), and the unique opportunities and editorial liberties she’s been given, including most recently becoming the Arts and Entertainment Editor of the New York Observer. She attributes her success to staying true to her passion & voice and never taking herself too seriously - we attribute it to her natural talent.

What You’ll Learn:

  • Why childhood influences shouldn’t be ignored.
  • The value of having a scripted response (and perhaps more than one) in potentially overwhelming situations.
  • The importance of finding ways to evolve while staying true to yourself - for both businesses and individuals.
Direct download: SIAB_DGrant_v3.mp3
Category:general -- posted at: 11:06pm EST

Firat Parlak is a true problem solver, but his path to becoming a professional User Experience Designer came about through a series of unconventional steps. As a 14-year-old, he immigrated to the United States from Turkey, landing in New York City with equal parts ignorance and motivation. Determined to make a life for himself, he spent all of his energy focusing on high school, after school language classes, and working as a Flash developer through the contacts he made scouring Craigslist. What culminated was a refined sense of problem-solving, both personally and professionally, and an unprecedented self- and circumstantial- awareness with which to approach those problems. Today, as the founder of Awesome, a mobile design agency, he is now applying these life lessons not just to the work he does with his team, but also by educating others. His most ambitious education project is a program aimed to bring the vocational studies of User Experience to the incarcerated, a challenge given that the audience has no access to modern technology and internet. Over sauvignon blanc provided by ABC Wine Co., he explains that while his journey has been winding, he maintains that with passion “not everyone is made for UX, but anyone, not matter who you are, could be made for UX” as long as empathy remains the core of what you do.

What You’ll Learn:

  • Why emotional intelligence can be just as important as formal training and education.
  • Key advice for getting started in UX and the first decisions you should make.
Direct download: SIAB_FParlak_v3.mp3
Category:general -- posted at: 12:27pm EST

If anyone has been at the forefront of innovation in media and technology for as long as the World Wide Web has existed, Elizabeth Osder can certainly claim that title. Growing up in Englewood, New Jersey, one of her earliest memories was spending time in the local print shop with her mom - a graphic designer - basking in the scent of the ink and sitting in awe of the prints she’d made; it was those experiences that inspired her to become a journalist. However, as she delved into her studies and career, particularly in photojournalism, she ultimately had the realization that the infatuation was not actually with the printed materials she made, but rather telling the story mattered to her most. Over diet ginger beers, Elizabeth talks about how it was this mantra that has kept her at the forefront of technology; from helping launch the first version of the New York Times online, shaping the digital focus of NYU and Columbia University’s journalism programs, and today as she helps reinvent video strategy and experience for local news companies. While her path has certainly been winding and the industry is ever changing, her charge remains: never lose sight of the bigger picture - the story.

What You’ll Learn:

  • The most important key to creating the best work is to put together a team of professionals that can solve the problem.
  • Why tenure is a killer of innovation.
  • The danger in people caring more about where they are doing something rather than what they are doing.
Direct download: SIAB_EOsder_v3.mp3
Category:general -- posted at: 2:14pm EST

Direct download: SIAB_CBrown_v3.mp3
Category:general -- posted at: 2:20pm EST

Prita Kumar boasts an impressive resume where her academic accolades are only surpassed by her practical experience. As a NYU Stern graduate, her trajectory seemed clear as she embarked on a life in the world of finance. However, an incessant need to problem solve paired with an MBA from Harvard Business School drove her to create a product she truly believed in. Over glasses of Chardonnay provided by Alphabet CIty Wine Company (, she discusses how her concept for Booya Fitness - a streaming group exercise class experience - immediately caught on, winning grant money and sponsor backing, gaining an audience, and potential investors. Booya’s a momentum was fueled by Prita’s hard work facilitating all parts of the business, a drive that kept Booya moving forward in an uphill battle against the saturated intersection of content and fitness. Unfortunately it was a battle that Prita ultimately realized was going to prevent her from ever reaching critical mass. This Story in a Bottle shows the excitement of potential success, but illustrates the true challenges of how to stay afloat and even pivot when you desperately believe in your idea and just need that “one more thing” to keep you going - and how to pick yourself up when that one thing arrives too late.

What You’ll Learn:

  • How wearing multiple hats as a founder can ultimately inhibit the business
  • The challenges of running a business for three and a half years on a shoestring budget
  • Navigating the the myriad advice you receive as a founder - because everyone has some and not all of it is right for you
Direct download: SIAB_PKumar_v3.mp3
Category:general -- posted at: 1:29pm EST

Jesse Middleton is, at his core, a problem solver. Early in his career, he used this ability, in addition to his natural curiosity of the internet, to found and “pivot” several companies. Ultimately, his trial and error  of his businesses lead him to partner with the then-budding coworking space, WeWork, adding to their suite of offerings as co-founder of WeWork labs. However, as the company grew exponentially, so did Jesse’s role, and in that growth,opportunity struck again. Now, as a VC at Flybridge, he uses his valuable problem solving skills along with the knowledge he’s gained as an operator to invest in and advise the companies seeking his support. Over dirty martinis, he explains the key characteristics that have helped his career thrive: the importance of a familial atmosphere when approaching business, overcoming the obstacles of being an introvert, and through it all, why every major decision he’s made ultimately comes down to what feels right.

What You’ll Learn

  • Why being suspended from school is not always a bad thing
  • How transparency with your investors is core to your relationship
  • How problem solving is a unique skill in and of itself - especially for operators
Direct download: SIAB_JMiddleton_v3.mp3
Category:general -- posted at: 5:41pm EST

While Jocelyn Leavitt has had a clear goal throughout her academic and professional career - to make education more accessible - her path to achieving it has been anything but. The spark was ignited while she was majoring in geography at Dartmouth, however, since then she’s spent her time teaching the underprivileged in Hawaii and New York, earning an MBA from Columbia University, pursuing a path in private equity and real estate before ultimately starting in the software space. It’s this varied experience and drive to bring inclusivity to the tech world that’s given her a unique set of skills suited to create Hopscotch - the only application optimized to build and consume apps exclusively on mobile. Over micheladas from ABC Beer Company, she describes their growth since launching in 2013, and the success in continuing to inspire kids ages 9-12 in their early stages of programming to create and play games and hopefully start a lifelong love of making.

About this episode:

  • Why not having a technical background shouldn’t deter anyone from innovating within the space
  • The differences in the startup and tech scenes in New York versus San Francisco
  • How computer science can and should influence younger generations
Direct download: SIAB_JLeavitt_v3.mp3
Category:general -- posted at: 9:07am EST

Nihal Mehta has been investing in the mobile space for the last 15 years, long before he became General Partner of Eniac Ventures. In fact, he started his career founding one of the earliest mobile ad products, long before the smartphones and ad buys we know today. In those early days he invested his time and effort chipping away at the potential the mobile space offered. After seeing many successes and failures as a multi-company founder, exits to companies like Omnicom and Google, and the evolution of technology and honing his expertise, he now spends his days advising companies with founders who share his passion for the industry. Over Pinot Noir he explains what inspired him to get started in this, then, largely uncharted territory and how his experience as a founder makes him uniquely qualified to invest today.

What You'll Learn:
- What early stage companies should do before they raise
- Why former founders make optimal VC partners
- How investing in early technologies can pay off

Direct download: SIAB_NMehta_v3.mp3
Category:general -- posted at: 8:36am EST

It’s been said that “knowledge is power” and no one embraces that more than Elizabeth Green. She has dedicated her life and career to bringing information to the masses in the hopes of bettering the US education system. Over Campari and Soda provided by Alphabet City Wine Company, she remembers very distinctly the moment in highschool when she realized the educational inequities amongst her own group of friends. From then on she was compelled to a path of journalism - with the aspiration of shedding a light on this increasingly complicated industry. However, when the traditional newsroom fell short in it’s support of the coverage she felt so passionately about, Elizabeth took matters into her own hands to create a publication that would cover it correctly. Now, as the cofounder and CEO of Chalkbeat, a nonprofit education news organization with the goal of keeping regional educators abreast of policy within their industry, she faces a new set of obstacles. All this while still finding the time to continue to be a thought leader in the community and writing a New York Times Book Review Notable Book: Building a Better Teacher: How Teaching Works (and How to Teach it to Everyone)”

What You’ll Learn:

  • How and when journalism can effect real change
  • As a founder: the importance of empowering a team to put their best work forward
  • The anxieties of being a startup founder and business owner at different stages of her company’s lifecycle
Direct download: SIAB_EGreen_v3.mp3
Category:general -- posted at: 5:53am EST

Rob Markman is the storyteller’s storyteller. Growing up in the in the heart of the cultural epicenter that was Brooklyn in the 80s & 90s, during the birth of rap music, he was hooked on to the genre early on. However, when his friends’ interests halted at memorizing the lyrics to Slick Rick or Kris Kross, he dug deeper. As he continued to mature, he did so alongside the music, eventually taking a chance on open mic nights and battling in lower Manhattan. Over Hennessey and Cokes, he tells us that at the core of this obsession has always been clear: to change the culture of how we talk about music and his innate drive to investigate the meaning and influence of each track in an encyclopedic manner. It makes sense then that as he entered into the professional world “journalism chose him” and he made a name for himself in the industry as Senior Hip-Hop editor for MTV (and also noted as one of BK Mag’s Most Influential 100). Now, as Artist Relations Manager at Genius, he’s even closer to realizing his goals than ever before, bridging the gap between artists and fans and helping to bring the heart of the story back to the forefront of the conversation.

What You’ll Learn:

  • The pros and cons of technology’s influence on the music industry.
  • How your passion can become your career in ways you may not have expected.
  • Why in a creative industry, the true star should be the work and not necessarily the artist.

Photo credit: Daniel Dorsa

Direct download: SIAB_RMarkman_v3.mp3
Category:general -- posted at: 1:18am EST

Maddy Maxey boasts a career path that spans a variety roles and industries - from Tommy Hilfiger to General Assembly she has covered the fashion and technology realms with fluidity and ease, and at 23, it’s only just the beginning. It’s a background that has not only returned high recognition like being listed as one of Forbes 30 Under 30, but has also  provided her the experience to recognize and carve out a unique intersection of the two industries - and led to the founding of her company, the Crated. Focusing on cutting-edge innovation, her company collaborates with others in the space to further the offering of wearable tech, and most specifically, smart fabrics. Over tempranillo provided by Alphabet City Wine Co. she gives us the fascinating perspective of how she was able to be a trailblazer in this industry, especially with the challenges of it being in its infancy, why not being popular in high school was ultimately a good thing, and that, above all else, being a maker is her single greatest motivator.

What You’ll Learn:

- How sometimes a hands-on education is better than following a university curriculum.

- Why it takes a certain personality to start a business.

- How to make the most of resources in the early stages of an industry.

Direct download: SIAB_MMaxey_v3.mp3
Category:general -- posted at: 9:49am EST

Andy Ellwood started his first company at the age of 12 - a lawn care business unlike your typical teen gig - one that stayed in the family, and passed from brother to brother for 19 years. That experience, paired with his focus on finance at Texas A&M, has set his course as an expert salesman since, with an emphasis on his unique ability to make a sale, regardless of the product. That’s why, when making the leap from his home state of Texas to New York City with no job prospects, his best friend of several decades knew he would excel as the biz dev lead for his budding tech company, Gowalla (even if Andy didn’t know what “biz dev” meant. Or API. Or anything about tech, really.) It’s a decision that has lead him further down the path of technology, ultimately leading to his latest venture offering major savings to offline shoppers: Basket. Over bottles Shiner Bock, Andy shared his milestone experiences: how a tough professor steered him into finance, the continued benefits of being an Aggie, and his theory for how he avoided a Texas accent.

What You’ll Learn:

- How your competition can be a great motivator.

- Why sometimes confidence that you’ll learn on the job is all the experience you need.

- What distance you’ll travel to save $10.

Direct download: SIAB_AEllwood_v3.mp3
Category:general -- posted at: 9:43pm EST

Alli Goldberg and Jen Jamula have made a career out of coaching people to face their greatest fear; public speaking. It's a position they ended up in almost by happenstance. As Yale University theater grads, these ladies set out as many post-graduation students do, subsidizing their passion for acting with jobs they found less than fulfilling. However, when the pursuit of theater also left them wanting, a chance reunion gave them the spark for an idea - creating their own kind of theater using the Internet's greatest content as the script of their production, Blogologues. And as that legitimized, so did the requests for coaching as well. By way of a shared office space, Alli and Jen became some of the more popular folks around the water cooler, where budding entrepreneurs pined for assistance in crafting and telling their stories. Over Rebel Yell Small Batch Reserve Bourbon compliments of Fool’s Gold, the Blogologues and GoldJam founders tell how they evolved at every turn, ultimately turning their speaking advice into tailored workshops for companies large and small, and their quest as faux tech people to reestablish verbal communication (by starting the no text weekend).

What you'll learn:
Why public speaking skills matter, even if you think you don't need them.
The importance of knowing your strengths as a founder, and how to hire for your weaknesses.
The value of communication in a text heavy, digital world.

Direct download: SIAB_Blogologues_v3.mp3
Category:general -- posted at: 1:25am EST

Dennis Mortensen is a serial entrepreneur, despite his best efforts to avoid it; seemingly ingrained in his blood, Dennis comes from a lineage of business owners and seeing their painstaking efforts while growing up, originally hoped to avoid that path. However, when his plan to pay off college debt went awry, his instincts lead him on an entrepreneurial course which has been his trajectory since. In those early days, after several successful sales and exits, his strategy was bold: doubling down on his successes with each new endeavor and angel investing the next. Ultimately he hit his first bust, a venture he’s since coined his “very expensive MBA,” which left him with 4 tickets to the caribbean and some soul searching. Over red bulls, a staple of his daily diet, Dennis tells us how he got up after his fall, still unable to shake his entrepreneurial drive, the successes he’s seen since by focusing on a single thru line; focusing heavily on analytics and inching closer to digital intelligence and automation. This is a system he’s closest to today as founder and CEO of, an artificial intelligence startup committed to solving the problem of calendar management once and for all, or as he puts it, “we schedule meetings.”

What You’ll Learn:

  • The pros and cons of building a business exclusively on cash flow.
  • Why your product focus should be being world class at one thing, versus half-assed at seven.
  • Why all no commercial websites should exist without analytics.
Direct download: SIAB_DMortensen_v3.mp3
Category:general -- posted at: 2:44am EST

When Brian Smith and Jackie Cuscuna met, they were teachers. However, as time would have it, their relationship and careers have evolved to a place they could’ve never imagined. Over a decade later, as their relationship evolved, a shared dream has come to fruition as the purveyors of some of the country’s most delicious ice cream, Ample Hills Creamery in Brooklyn, New York (and they are not your typical entrepreneurs). Over Dark and Stormies (and delicious Bourbon Street ice cream), they share their true entrepreneur story: what inspired and continues to inspire them as ice creamers, how that path was in jeopardy after only 4 days of business, and how a special relationship with Disney has gotten them beyond the dark side (and continues to help them grow). While the journey has certainly not been an easy one, the result is undoubtedly sweet.

What You’ll Learn:

  • How not being prepared for the best case scenario may be a problem.
  • Why in entrepreneurship you should dare to be bold and never be afraid to throw a hail Mary pass
  • The importance of remembering to keep a balance in work and life - and noting where the two can intersect
Direct download: SIAB_AmpleHills_v3.mp3
Category:general -- posted at: 1:54am EST

Jenny Boylan has spent her life and career in constant transition. She embodies this evolution not only as a personal motivator and measure for progress as a notable member of the transgender community, but professionally, as she encourages others to do the same, regardless of their pursuits. As writer and professor in the English Department at Colby College and now at Barnard College, she has helped budding writers find and refine their voices and love of the craft for over 20 years. As a writer, she’s authored thirteen books and dozens of short stories, more recently shifting from humor to share her personal transition through the likes of her memoir “She’s Not There: A Life in Two Genders” - the first bestselling work by a transgender American. Most recently she has become one of the de facto spokespeople and advocate in the LGBT community and appeared as a consultant and cast member on “I Am Cait” (amongst other efforts). Throughout, she has used her experience to empower others, helping them find their way within an often divided community. Over a selection of ABC Beer Co.’s favorite beers, she explains the obvious and not so obvious challenges she’s encountered: why not all transgender people are not created equally and the value of being honest about yourself in order to connect with others in a meaningful way.

What You’ll Learn:

  • Why making people laugh is great, but making people cry is better.
  • How division within a minority group can often be as detrimental as those who oppose them.
Direct download: SIAB_JBoylan_v3.mp3
Category:general -- posted at: 7:22pm EST

It has been said that often the truth is stranger than fiction, and no one demonstrates that more than Stephen Elliot, founder of The Rumpus. He has spent his life using writing and filmmaking as an outlet for expression when he often had nothing else. Growing up in group homes for orphaned kids in Chicago, he found himself in precarious situations and circumstances, ultimately at the helm of his own destiny. Over ginger beers provided by Alphabet City Beer Company, he describes exactly what that meant: negotiating his right to attend public school, why majoring in history lead to a tailspin with drug use, how he overcame that to get a Masters from Northwestern, all the while suffering the severe ups and downs that culminated in his life’s work. The results are captured in his novels and films, particularly his memoir, the Adderall Diaries, (and then the film about making the film that James Franco wrote and starred in). Today, as a contributor to Epic, he continues taking on new perspectives to tell stories, immersing himself in situations for months at a time in order to give the behind the scenes take on things like LA’s Silicon Beach, amongst others, as well as his own experience having a “real” job for the first time in his whole life.

What You’ll Learn:

  • Why sometimes having no money is better than not having enough money
  • What it’s like to go through your career without ever having a “real” job
  • What happens when you bring a dominatrix to a film premiere  
Direct download: SIAB_Elliot_v3.mp3
Category:general -- posted at: 1:09am EST

Michele Serro’s career has been driven by finding and seizing opportunities as they are presented to her. As a kid, this meant that a natural singing talent turned into a pursuit of an Opera career and training at both Julliard and Indiana University. However, when subjectivity and politics trumped her passion, she shifted her artistic abilities and soft skills to the world of design, where she was able to gain experience in product and innovation at IDEO, amongst other places. It was when she was confronted with the practical and emotional challenges of first time homebuying that entrepreneurship struck and she was inspired to “revolutionize, not disrupt” the real estate world with her company Doorsteps. Over negronis with campari provided by ABC Wine Company, she explains how, while unconventional, the path of her career and consistently being a “beginner” ultimately lead to her success as an entrepreneur, why that success should not only be defined by the acquisition of her company, and the challenges of figuring out what comes next.

What You’ll Learn:

  • The value of knowing your strengths as a founder and knowing which part of the process they should impact
  • How empathy and prototyping should drive design
  • Why founders should “date” ideas before building them
Direct download: SIAB_MSerro_v3.mp3
Category:general -- posted at: 12:14am EST

Oz Lubling’s lifelong obsession with the internet began at its inception; in a time when there were no rules or standards, this self-taught developer was always focused on creating products and pushing the envelop. This carried over to the foundations of his professional career -- a developer turned UX professional -- when both disciplines were largely undefined and Mountain View was still a rural town in Northern California. Over lychee martinis Oz recalls the course of his 20+ year career alongside the growth of internet; why being employee number one of the now digital agency behemoth Razorfish gave him a front row seat its evolution and how after several years he’s found his way back to making products with its co-founder, Jeff Dachis at One Drop.

What You’ll Learn:

  • The importance of context within product.
  • How even products which solve problems well can fail.
  • Why company culture may still have value in the modern tech world.
Direct download: SIAB_OLubing_v3.mp3
Category:general -- posted at: 8:49am EST

Allison Schrager doesn't see obstacles, only opportunities. As a student with no mathematical background she set out and earned a PhD in economics from Columbia University. When her graduate advisor failed her, she changed her trajectory and made a career as a successful pension economist. At the onset of the financial crisis of 2008, she transitioned to journalism. While her accomplishments and accolades across various industries are no short of impressive, most noteworthy about her is that the goals she strives to achieve seem to always sit at the pinnacle of what most would consider an insurmountable uphill battle. Over wine, Allison explains why she thrives in these challenging situations, why her dream jobs exists at the epicenter of finance and creativity, and how her enthusiasm may be her greatest asset.

What You’ll Learn:

  • Why obtaining wealth shouldn't be a goal for retirement.
  • How enthusiasm can bring opportunity, but doesn't replace hard work.
  • Why validation can be a motivator if you keep it in check.
Direct download: SIAB_ASchrager_v3.mp3
Category:general -- posted at: 8:59am EST

Wesley Verheove has made a career of helping others tell their story: from his time in the music industry, to partnering with startups, and most notably as a photographer, he finds the gifts that each brings to the table and helps to emphasize them. In his latest passion-project-turned-real-project, One of Many, he traveled to underrated art communities across the US to shine a light on them and unite makers in each; connecting them with others like them and giving them a platform to showcase their work. But what about the storyteller’s story? Over rose proviced by Alphabet City Wine Company, we heard from Wesley about how his patchwork background from rural Netherlands to Bloomington, Indiana and ultimately a bicoastal residency makes him uniquely qualified to be the one to unite the many.

What You’ll Learn:

  • Why you should follow your passions, even if the path seems unpaved.
  • Being successful in tech or art is not confined to New York or San Francisco.
  • How being a part of a team can ultimately help you become stronger as an individual.


Direct download: SIAB_WVerhoeve_V3.mp3
Category:general -- posted at: 10:24am EST

One of the ever-growing concerns as the digital world expands is what effect it will have on relationships; from business correspondence to social media to online dating, we’re constantly changing the way we interact with one another. Leading the charge in research and expertise, Andrea Syrtash is constantly monitoring and navigating the myriad perspectives and implications on modern relationships and advising on how to navigate them. A self-described “slasher” and naturally born advisor, her certified expertise spans across multiple forms of media as a coach, author, television personality, and most recently, podcast host. Over Chardonnay provided by ABC Wine Co., Andrea explains that while the problems she aims to solve can be complicated, her goal is quite simple: to contest the poor advice so often given in this space and to help people break free of their preconceived perspectives in order to find what suits them - from lasting companionships to a reason to swipe left.

What You’ll Learn:

  • The single thing that both men and women want in relationships.
  • How perspective becomes reality and how to changing it may be important.
  • Not all expertise comes from experience; sometimes the best way to advice comes from learning from others.
Direct download: SIAB_ASyrtash_v3.mp3
Category:general -- posted at: 7:51pm EST

If there’s one constant in the startup world it’s that no two companies can follow the same path to reach the same conclusions; LearnVest is no different. Over Ridge Three Valley Zinfandel, CFO and cofounder John Gardner recounts their very comprehensive story. As a hedge founder founder seeking an alternative path, he started the company from the ground up in a partnership between himself and his cousin Alexa. Over time, they grew and evolved that business in both size, offering, and locations, all the while setting and achieving goals only to reset and start the process again. It’s because of this laser sharp process and their keen ability to surround themselves with both subject matter experts as well as be inspired by universally innovative thought leaders which lead to their eventual, successful exit to Northwestern Mutual (and the work doesn’t stop there).

What You’ll Learn:

  • The importance of creating the narrative for your product, especially if it doesn’t exist.
  • How to approach growth incrementally and the importance of being comfortable with evolving the product versus having it all on day one.
  • Why striking a balance in experience with both employees and board members is key.
Direct download: SIAB_JGardner_v3.mp3
Category:general -- posted at: 9:18pm EST