Episode Stack: https://stackl.ist/4sSOZBB

Andrew Boos is the founder of Darwinian Ventures, a fractional sales advisory firm that builds go-to-market teams for early-stage B2B startups. He's also quietly investing in his own clients from profit, not a fund.

Before Darwinian, Andrew had a profitable exit at 24 from a startup that began as an ad exchange for China (yes, really), fell into post-exit depression nobody wanted to hear about, learned enterprise sales under a CRO with a $4.2 billion annual quota at a Sutter Hill incubation, blew his exit money trying to launch a quantitative hedge fund, and started freelancing to pay rent when law firms came knocking.

We talk about why a linear path to entrepreneurship is a privilege, what happens when your North Star disappears after an exit, how he built Darwinian from a solo 1099 gig into an embedded sales team that's worked with 100+ startups, and why he's now writing small checks into companies where he can see product-market fit before the founders do.

🔗 Episode Stack: Link on Stacklist

AI is moving so fast that it's hard to know what to pay attention to and what to tune out. In this episode, Michael Hoy (co-founder and CEO of Atlas) and I dig into what it feels like to build a company during the most disorienting moment in tech most of us have ever experienced.

Michael shares the full Atlas origin story, from winning Product Hunt's product of the day, week, and month, to the humbling realization that 1,200 users didn't translate into a single paying customer. We talk about why the startup advice machine creates more noise than clarity, how AI is shifting from exciting to existential, and why the founders who win are the ones who learn to trust their own signal over everyone else's opinions.

We also get into Michael's vision for where Atlas is headed: a trust layer for the coming agent-to-agent economy, and why that future might be closer than most people think.

Topics we cover:

• Why this month felt like AI truly woke up.
• Building 12 projects in a week and what that means for everyone else.
• The gap between Product Hunt traction and real product-market fit. Education-based marketing that leads with curiosity, not fear.
• Doing things that don't scale on purpose.
• Michael's advice to founders: trust what you're feeling and shut out the noise.

Episode Stack: https://stackl.ist/4rYFAYM

8 years in corporate sales. One birthday trip to Hawaii. Quit mid-vacation. Became Miss Hawaii 2025. Built a retreat business.

All in 24 months.

Nicole Miranda's timeline sounds impossible. It's not.

This episode is about what happens when you stop optimizing for other people's definitions of success and start trusting that you're on the right river.

We covered:

- The moment she quit her sales job

- Manifesting Miss Hawaii with Dr. Joe Dispenza

- Building Six Degree Soul (tours + retreats)

- Upcoming events in Oahu (August) and Bali (October)

- Why "follow your passion" misses the point

For anyone stuck in a "good" job that's killing them.

Episode Stack: https://stackl.ist/4qaixcK

Summary

In this episode I sit down with Vlad Cazacu, Founder and CEO of Flowlie, to talk about the long, winding path that led him from an immigrant kid obsessed with science magazines to building one of the most thoughtful fundraising tools I’ve used as a founder.

We go way back. Before Flowlie was helping founders raise hundreds of millions of dollars, Vlad was running a textbook startup in college, turning down an acquisition offer because it did not feel big enough at the time. That early mix of curiosity, naivety, and ambition shows up again and again in his story.

Vlad spent years on the investing side, working in venture capital and family offices, seeing thousands of deals and learning how capital actually moves. Flowlie did not start as a founder product at all. It began as an internal tool for investors, then pivoted after founders started asking a simple question: “Are we even a good fit for these investors?” We talk about the shoebox office in Miami, the moment Stripe lit up with their first paid users, why fundraising is mostly unnecessary overhead, and how AI should remove friction instead of adding noise. This is a true zero-to-something story, told while still very much in motion.

Key moments we cover:

• Growing up in Romania and falling in love with building through curiosity
• Building and shutting down a college startup after turning down an acquisition
• Writing a book before ChatGPT and how it unlocked a VC career
• Why Flowlie started as an investor tool and pivoted to founders
• The first Stripe notification that made everything feel real
• A future where founders only show up for investor meetings

Key takeaways:

• Naivety is often a feature, not a bug, in early founders
• Fundraising is a system problem, not a confidence problem
• The right tool removes emotional and cognitive overhead

Chapters

00:00 The Naivety of Startup Beginnings

03:03 The Journey to Entrepreneurship

06:07 The Birth of Barter Out

09:01 The Influence of Family and Curiosity

12:04 Lessons from Early Ventures

14:55 Transitioning to Venture Capital

17:58 Building Flowlie: The Next Chapter

22:57 The Pivot to Founders' Needs

30:00 Building the Team and Culture

37:05 Funding Journey and Growth

38:13 Future Vision and AI Integration

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/3QPuHaW

Ever wondered how creativity meets entrepreneurship? Dive into this conversation with Kyle Hudson and Will Taylor on "Zero to Umm..." where they chat about Will's journey from a physicist in a creative family to launching startups.

Get ready for some raw insights as Will reveals his experiences with a CV writing service, on-demand dry cleaning, and solving logistics with tech-driven solutions. They talk about the ups and downs of risk-taking, the grind of starting from scratch, and why failure is just another chapter in the entrepreneurial story.

Plus, hear about the tech behind Will's current venture, Workflow, where simplicity meets power in creative collaboration tools. The conversation covers the importance of validating ideas with real users and the charm of maintaining a small, effective team.

So if you're into creativity, startups, or just need a push to venture into the unknown, this episode's packed with relatable stories and valuable lessons. Don't miss out—catch the full episode now!

Send us a text

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

Summary

In this conversation, Cristina Cordova shares her journey through the startup ecosystem, detailing her experiences at various companies including Tapulus, Google, Stripe, Notion, and Linear. She discusses the importance of company culture, the role of partnerships in growth, and the significance of finding the right fit in a startup. Cristina emphasizes the value of working with strong founders and the need for startups to have a clear vision and product-market fit. Her insights provide valuable lessons for aspiring entrepreneurs and those looking to navigate the tech industry.

Chapters

00:00 The Journey into Startups
11:24 Finding the Right Fit in Tech
18:20 Building Relationships and Partnerships
23:59 Building Payment Infrastructure: The Early Days of Stripe
29:19 Transitioning to Notion: A Personal Journey
36:04 Joining Linear: The Right Fit and Company Culture
44:02 Key Insights for Startup Success: Lessons Learned