188: Join the Club

Happy Lunar New Year! 🐲🧧🐉

It’s the year of the Dragon, which is my wife (and my dad’s) ben ming nian, literally “root life year”. You’d think this would make it a lucky year, but it’s traditionally seen as a year of potential trials and misfortune.

So if there are Dragons in your life, give them an extra blessing when you see them for the next 12 months may contain some calamity.

It’s bizarrely warm for February in New York but I admit I've been enjoying the crisp air and sunshine of this mild winter.

I wanted to take a moment to reminiscence about a special group that played a significant role in my life when I first moved to New York. It was called Scotchrepreneur, and it was an incredible gathering of entrepreneurs who bonded over scotch and shared their problems.

The group was the brainchild of Derek Flanzraich, founder of Greatist and Ness. We had connected back in San Francisco in 2010. He moved to New York soon after, and when I finally arrived in 2014, he invited me to be part of this unique community. Every month, Derek would host the gatherings at his apartment, where we would each contribute $20 and indulge in a fancy bottle of scotch. 

One of the highlights of these meetings was reading the tasting notes that Derek put together. He would collect them from different whisky review sites across the web, and they were not your typical descriptions. We would laugh notes at like matchsticks, old band-aids, and even mushrooms grown in a basement. It made us feel cultured while taking a playful jab at the tasting notes industry.

I know you might be thinking that this sounds a reinvented "good old boys club," but Derek made sure the group was diverse and inclusive. He maintained a list of individuals who were thoughtful ambitious, and kind. While many of the regulars were men, there were several women who also became fixtures within the group, and seeing them build incredible businesses (one while becoming a mother) was inspiring and our conversations were respectful.

The format was simple: we split the scotch, and you brought your snacks and alternative beverage you wanted to drink. The opening question of each session was always the same:

"What is your biggest challenge?"

This part was intense and insightful. We would dig deep into each person's issue, offering advice and support. Sometimes, these discussions would take hours, but they were truly transformative.

The booze helped create a sense of vulnerability and we would drink and enjoy ourselves until the word "Scotchrepreneur" became a challenge to pronounce. At that point, we knew it was time to slow down. I know these days there are a lot of folks who are going sober or are cutting back their alcohol consumption, which makes sense, but I think in this environment the drinking really did help.

Derek really set the tone for going deep—fake challenges like "I think we're growing too fast" were batted away and in favor of questions like "I can't stand my cofounder" or "we're running out of money in 3 months".

Scotchrepreneur played a crucial role in many founders' lives, including mine. We tackled problems like dealing with difficult employees, making tough decisions about relationships, and so much more. Many agonizing personnel decisions and even personal relationships were rewritten thanks to this monthly forum.

Sadly, COVID caused Scotchrepreneur to close down. We attemptted to move online but trying to replicate the experience of drinking scotch in your living room while looking at a screen full of faces just wasn't the same. Many people also started moving out of the city. Derek had sold his first company the year prior and he and his wife Sarah wanted to get out of New York. This ultimately spelled the end of the group as we knew it.

I'm not sure if Derek has restarted this program in Austin, where he now lives. He‘s also become a father, and I can understand that dedicating an entire Friday evening and dealing with a potential hangover may not be as doable as it was in our twenties and early thirties. But I am really grateful for the amazing journey we had together over the years.

Scotchpreneur showed me the power of community, ritual, and a catchy name. Despite making no money on this project, I have no doubt it has been one of his many legacies as an entrepreneur and builder.

Do you have a Derek or a Scotchpreneur in your life? I’d love to hear about it.

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As I shared in this newsletter, community can be a powerful force for personal and professional growth. Which is why I want to tell you about to really special community oriented programs you might want to check out.

The Platform Launchpad—I completed this 6 week personal publishing cohort a few months ago and it is not hyperbole to say it transformed my relationship to posting. I'm seeing incredible results on LinkedIn and Eric and Kasey are truly mensches. Their next cohort starts Feb 19—sign up using my link here.

The Next Chapter—This is my first ever group coaching program, at a price point that's more accessible that 1:1 coaching. It's designed for midcareer outliers—creative professionals who are in transition from job to startup, from sabbatical to next venture, or some other kind of transformation.

If you've ever thought about working with me, but felt the pricing might be a little steep, this is a perfect opportunity for you. Learn more and apply here.

—Jason

Recent Issues

How I Can Help You

As most of you know, I'm now a full-time coach and CEO via my firm Refactor Labs. With that, I have a couple ways I can help. Reach out if any of these speak to you or your organization.

🧢 Executive Coaching: 1:1 + small group sessions that unlock transformational growth through extended partnership.

🛠️ Participatory Workshops: Interactive seminars designed to learn and practice crucial skills for navigating complex transitions—storytelling, emotional intelligence, experimentation and more.

🎤 Keynote Talks: High energy presentations that challenges audiences to dream bigger and act bolder in the pursuit of excellence.

Coming soon: Templates, exercises, and other low-cost ways to build resilience and develop your outlierness.