Dive into the raw, unfiltered journey of startup founders and CEOs as they navigate the tumultuous waters of entrepreneurship. "Zero to Umm..." flips the script on typical success stories, focusing instead on the pivotal moments of uncertainty, fear, and adaptation that truly define a startup's path.
Jared White (Matey AI): Building AI You Can Trust in a Courtroom
Episode stack: https://stackl.ist/4baJeZm (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
25 Jun 2026
The Vision. Unfiltered. (Here's Where We're At)
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
29 Apr 2026
Cody Schneider (Graphed): What It Takes to Build AI Marketing Agents That Work
Episode Stack: https://stackl.ist/4vWPzAl (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
Inside a recent episode
Thomas Peham - Otterly.ai
Published 15 Apr 2026 · Transcript excerpt
[…] And I look at this in the sense of We're still so early in this whole AI game and it's going to be massive. It's going to be massive. And the question I receive a lot from brands and marketing teams is, Thomas, is my website even relevant in six months, right? Is my marketing as I do marketing right now even relevant in six months or in a year from now? I always mention two things. I really believe there is a role, like there will be marketing managers, marketing people working in businesses, obsessing over the creative side of things, the storytelling side of things. And then there will be technical marketers doing technical things, implementing agents and whatnot. […]
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