Zero to Umm...

Episode stack: https://stackl.ist/4baJeZm

We taught computers to do math, then to write. Jared White thinks the real unlock is teaching them to read, and he's proving it in the one place that punishes a wrong answer hardest: the courtroom.

Kyle sits down with Jared, founder and CEO of Matey AI, whose path runs from building quantitative trading desks in Austin, through a stint in crypto, to an AI-native legal company built for criminal defense.

They get into why he started in the least forgiving domain he could find, how the economics of building have flipped, and the advice he'd give a younger founder: start with the customer, because implementation is the easy part now.

In this episode:

0:00 Intro — coffee mugs, merch, and a Matey logo story
5:35 Pricing as a moving target (version 18 and counting)
7:33 Reading a Cursor bill as an asset, not an expense
10:26 Jared's path: software, burnout, and building a trading desk
17:25 Naming Matey: the Wordle of the day and "your first mate"
20:22 Why this feels like the early web all over again
24:34 When AI coding finally got good enough to trust
28:17 Why start in legal — the least forgiving problem
30:55 "Executive Mate": an AI that could run a company
31:49 Scaling the team, hiring misfires, and the data problem
37:37 Human-in-the-loop, shrinking toward zero
40:38 The raise, and a go-to-market year ahead
50:19 Advice to a younger founder: start with the customer

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

My podcast guest couldn't make it today. So I figured I'd just tell you where we're at.

What came out was probably the most honest version of the Stacklist vision I've said out loud: why the internet has been broken since 1995, why your website and Instagram and LinkedIn are all symptoms of the same problem, and what we're actually building to fix it.

No deck. No script. Just 9 years of thinking, a slice of pizza, and where we're going.

In this episode:

00:00 – Intro
00:39 – Why we've all normalized chaos online
03:03 – What we're actually building (it's not an app)
05:29 – How it works for people
06:30 – How it works for businesses
10:18 – What's wrong with Linktree and what we built instead
12:45 – The link between brands and people
14:00 – Spark → match → fire → fireball

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

You've heard the pitch: AI agents that run your marketing, write your content, manage your ads, source your leads. It sounds like science fiction, or at minimum, like something that works for someone else's company. Cody Schneider has actually built it. In this episode, Cody, co-founder of Graphed, former growth lead at Rupa Health, and serial builder from Coeur d'Alene, Idaho — sits down with Kyle to get specific about what's real and what's hype in the AI go-to-market space. He's not philosophizing from the outside. He built a sourcing agent before breakfast the morning of this recording.

Discussion topics:

- Why "just give an agent a task" fails, and what agent orchestration actually looks like when it works
- The AI SDR post-mortem: why those tools didn't fail because AI is bad, and what the wrong optimization metric actually costs you
- How Cody thinks about "biology": whether an idea has the structure to become a real company or a good side project
- The compounding go-to-market loop: layering channels, acting on signal, and why you never stop what's working
- Data quality as the hidden killer of every AI analytics project (including why your Facebook ads API data is probably wrong)
- Vibe coding from 0 to 80% vs. 80% to production & why that gap is where companies get stuck
- What a GTM engineer actually does in 2026, and why that skillset is one of the rarest in the market right now
- The future Cody is betting on: agent teams, services bought as outcomes, and what happens when the cost of intelligence approaches zero

Key moments:
[00:00] Board meetings with your agents
[01:00] An agent Cody built before 8am and what it did [04:12] How Cody evaluates whether an idea has "biology" to be a real company
[08:56] From Etsy scraping to Rupa Health: the origin story
[15:48] Signal and noise — acting fast when you have it
[18:00] Why AI SDRs failed (it wasn't the agents)
[22:12] Software that molds to the user: the end of dropdown UIs
[27:12] Vibe coding's dirty secret
[33:06] Where Cody sees Graphed in six months
[49:15] Cody's homework for non-technical founders right now
[52:30] Kyle's live Graphed demo: Apollo, Stripe, QuickBooks, Brex, and PostHog in one afternoon

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

Steven Plappert closed Forecastr's Series A the day before his last payroll would have cleared the bank. Six weeks later, he's sleeping eight hours a night for the first time as a founder.

In this episode of Zero to Umm, Steven and I trace the full arc: failing his first company after three years, walking the Appalachian Trail from Georgia to Maine, meeting his co-founder Logan Burchett by accident at a CFO shop in Louisville, and building Forecastr through six years of round-to-round survival.

Key topics:

• Why curiosity, a greatness obsession, and a high tolerance for volatility pointed Steven toward entrepreneurship
• The FantasyHub shutdown that paid him $12,000 a year for two years — and the identity crisis that followed
• 2,000 miles on the Appalachian Trail and the idea that wouldn't stop nagging him while he walked
• The second-time founder playbook: why Steven never raised without a paycheck and never dropped below three months of runway
• Hell Week at Christmas 2020 — four people hand-migrating 100 Google Sheets models into the new product
• The Series A that died when Silicon Valley Bank did
• His Iron Man suit philosophy: why Forecastr is building for a human in the loop, not against one

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

Thomas Peham spent a decade building marketing engines for other people's companies — from a tiny PLG startup to a venture-backed company that raised $138M in funding. Then he noticed something that changed everything: ChatGPT was answering questions his clients used to win on Google, and nobody had a way to measure it.

In this episode, Thomas shares the full story behind Otterly AI — from the aha moment in his car to a Product Hunt launch with no pricing, a TechCrunch feature before Christmas, and scaling to 20,000 users in a single year without taking VC money.

Key topics:

• Growing up in Austria with no business background and stumbling into SEO through HTML hobby projects
• Building Usersnap's inbound engine from zero marketing budget to seven figures through content alone
• The moment he realized AI search was going to disrupt everything he'd spent years mastering
• Launching on Product Hunt with a "super scrappy" product and no pricing page
• Why 15% of website traffic now comes from AI agents — and what that means for marketers
• Bootstrapping a 17-person company in a category that didn't exist two years ago

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.