Story In A Bottle Podcast

As we’ve learned, there is no clear path to successful entrepreneurship and Alanna Gregory’s story is a shining example of that. With an engineering background and beginnings in the world of finance, she was unexpectedly struck with inspiration. Now, as the co-founder of Vive, an on-demand blowout scheduling app for women in metropolitan areas, she’s had to continue to make a lot of risky decisions in order to grow and pivot her business. Over pinot noir, generously provided by Alphabet City Wine Company, she talks to us about the importance of assessing the data at every turn, but that ultimately your passion for your company is paramount to your success.

What you’ll learn:

- Sometimes data doesn’t tell the whole story

- How pivoting in life and in your company can be a saving grace

- Why the motivation of founding a company should be more than big business

- Why it’s important to put something out there, even if it’s not 100%

Direct download: SIAB_AGregory_v3.mp3
Category:general -- posted at: 12:25pm EST

Chris Messina says he has lived a life “peppered with serendipity.” A native New Englander, he’s also lived a life that truly embodies the spirit of the internet - a place where everyone has an equal voice, where democracy enables true societal progress. At least in theory. Over Failla Pinot Noir, Chris discusses his high school days in New Hampshire, battling his school to ensure the Gay/Straight Alliance had a place on its website (a battle which almost cost him his diploma), helping develop web standards with the launch of Mozilla, using pioneering social media tactics to launch BarCamp, and how no matter what he does, it’s about continuing in a career he 100% believes in.

What you’ll learn:

  • The challenges of web design in the early days of the Internet
  • The story behind the invention of the hashtag (#)
  • How web standards have remarkably improved the state of product creation
  • How his event, Barcamp, helped launch Techcrunch, Pandora and Flickr
Direct download: SIAB_CMessina_v3.mp3
Category:general -- posted at: 7:49am EST

There comes a time when a person struggles with the “What If” moment in their life and/or career. For Alexandra Cavoulacos, that fork in the road came when she had to decide between continuing down the stable and successful partner track as a consultant at McKinsey or to throw caution to the wind and create her own company, The Muse, a startup she co-founded with Kathryn Minshew. Over glasses of Alsatian white wine, generously provided by Alphabet City Wine Company (, she discusses how she and Kathryn had been burned creating a startup once before and why, since choosing the startup route, she hasn’t looked back.

What you’ll learn:

- The myths and benefits of going through an accelerator program, and why the prestige should not negate the hard work it takes.

- How the stresses of a startup evolve and change as you achieve success.

- Why it’s important for founders to put themselves outside of their comfort zone; “just fucking launch.”

- Gender biases and how to navigate them in raising venture.

Direct download: SIAB_ACavoulacos_v3.mp3
Category:general -- posted at: 5:01pm EST

The medical industry, while growing and innovating all the time, appears to be stuck in the past; often leaving patients needing something more user friendly. Jay Parkinson, MD, is trying to rethink that world, leveraging the benefits of technology and the emotionality of humanity. He founded Sherpaa in 2012 in order to make health, medicine, and insurance more accessible to everyone. And he’s just the guy to do it; while he’s a pediatrician by training, he has a clear aptitude for systems thinking (a quality which is actually antithetical to the competitive spirit encouraged in med school).

Over Bulleitt Bourbon, provided by Alphabet City Wine Company, we discussed how he’s a taken a problem solving approach and an always-ask-why mentality since med school, and how it’s lead him to focus on creating patient-centered practices and products utilizing technology to actually help people with ease.

What you’ll learn:

  • The parallels between digital product creation and innovation in the medical industry
  • The importance of always remembering to ask “why?”
  • Why sometimes the best thing to do is the simplest.
  • How medicine is too often overly tied to tradition.
  • What having a cofounder and having a spouse have in common.
Direct download: SIAB_JParkinson_v3.mp3
Category:general -- posted at: 7:39am EST