Episode Stack: https://stackl.ist/48R3vkY

Don't miss this episode. I loved this conversation with Stephen Messer, who co-founded LinkShare with his sister in the late 90s and sold it to Rakuten after about 10 years. He's now building Collective[i], an AI platform that makes your professional network actually usable.

Stephen walked me through the first four years of LinkShare when they lived in one apartment, rotated shifts on two computers, and he worked directly on the main server because they couldn't afford another machine. During their pitches they had to spend first hour explaining what the internet was before they could even talk about the business. Revenue didn't grow until year six or seven because they charged 2% per transaction and needed massive volume.

One of my favorite stories: Michael Dell called him on a Sunday night and Stephen thought it was a prank for 30 minutes. That partnership changed everything. The first retailers all said "call us when you have affiliates," but direct marketers like Omaha Steaks understood the model from catalog days and signed up first.

Stephen was honest about why the skills from one successful company don't always transfer to the next one, why venture capital from top-tier firms isn't always worth the price, and his one rule for founders: never live above the second floor because the emotional swings will make you want to jump out the window at some point.

His take on most startup advice: ignore it and find your own style. Really appreciated Stephen's time and honesty about what building actually looks like.

Episode Stack: https://stackl.ist/3XlwM1O

I met Tracy in Hawaii when we were midway through our Blue Startups accelerator program. Tracy coaches founders, and also serves as a Mentor in the Blue Startups program.

Tracy came in and told such authentic (both inspiring and difficult) founder stories. We connected after and was thrilled she agreed to join us on Zero to Umm to tell some of those stores.. and more.

Tracy is the Co-founder and former CEO of Chewse, a corporate catering platform she launched from her dorm room, raised $40M for, and successfully sold in 2020. She now serves as an executive coach for founders, helping them navigate the intersection of leadership, mental health, and personal growth.

No matter what stage of the journey you're in, there's something valuable for you in this episode.

Takeaways

• Authenticity is crucial in fundraising.
• Building a startup is an emotional journey.
• Resilience is key to overcoming challenges.
• Staying true to oneself leads to success.
• The importance of a supportive team.
• Navigating the ups and downs of entrepreneurship.
• The role of personal growth in business success.
• Balancing personal and professional life.
• The impact of mentorship and guidance.
• Embracing change and transformation.

Send us a text

Episode Stack: https://stackl.ist/3W1QAGR

I had THE BEST conversation with Caroline Clark, Co-Founder and CEO of Arcade, about the journey from zero to building a product that's changing how teams create interactive demos.

We talked about her path from consulting to product marketing at companies like Atlassian, and what led her to start Arcade. What stood out to me was her honesty about the hard parts of building a company. The burnout, the failed launches, the moments at 4:30 AM questioning everything.

Some things that stuck with me:

• Why the best market isn't always the obvious one
• The real cost of being on the hook for marketing output (and why she built Arcade)
• How a "failed" product launch became their most successful enterprise offering
• The importance of staying close to what brings you joy when building

If you're in the early stages of building something, Caroline's advice about being passionate and not getting too attached to one-off moments is worth hearing. She's built up what she calls a "lower bar for embarrassment" over time, which feels like an underrated founder skill.

Chapters

00:46 - Introduction and Background
11:52 - Early Career and Transition to Marketing
25:21 - Joining Atlassian and Learning from Failures
34:12 - The Importance of Market Fit
45:44 - Venture Capital Insights and Growth Mindset
56:30 - Building Arcade: Challenges and Successes
1:09:18 - Future of Arcade and AI Investments
1:22:14 - Advice for Aspiring Entrepreneurs