🚨 NEW: Cameron and I are super happy to be launching the Traction Lab Venture School, a new program to help founders of early-stage startups find paying customers. Kicks off March 23rd. Only 20 spots. You in?

Hey friends 👋

It’s almost a cliché. Some VC tells you to “go bigger” on your fundraise, another investor says to keep it small, and you’re stuck in the middle.

So in this episode, we tackle one of the most confusing decisions founders face: how much money should you actually raise? We break down the false dichotomy of “go big or go home” and why ego has no place in fundraising decisions.

We dive into three realistic scenarios where founders are wrestling with round size—from a bootstrapped SaaS founder being pushed toward a $2M round when they only need $500K, to a profitable fintech debating whether to raise at all, to an AI startup running out of runway with thin traction.

The key insight? It’s all about capital efficiency and what you’re actually buying with that money. In early stages, you’re buying learning, not growth—and 10x the money doesn’t mean 10x the learning.

Our hot take: raising too much too early can actually screw you over when it comes time for your next round. We also get into why you need to understand investor business models—their “right size” round might not match your stage at all.

In our Frivolous Thoughts segment: JDM battles his display link monitor (send help), and Cameron updates us on the Kings’ ambitious 16-game losing streak. Yes, he said ambitious. 😅

—Cameron and JDM

🚨 NEW: Cameron and I are super happy to be launching the Traction Lab Venture School, a new program to help founders of early-stage startups find paying customers. Our first cohort kicks off on March 23rd, and spots are limited. Learn more →

Hey friends 👋

Ever had a big enterprise prospect come knocking and suddenly your entire startup strategy is up for debate?

Yeah, we see this all the time…

So this week we’re tackling the seductive allure of enterprise deals. You know the ones—big logos, bigger contract values, and that intoxicating feeling of “legitimacy.”

But it’s never that simple, is it?

Most enterprise plays are distractions dressed up as opportunities.

Long sales cycles (6-18 months vs. weeks), customization demands that kill repeatability, and the classic trap of pausing your working sales motion to chase a single whale.

We dive into three real-world scenarios in which founders are considering an enterprise pivot. From cybersecurity tools chasing Fortune 500 pilots to legal tech crushing it with small firms but tempted by big logos, we break down each move and rate it on our conviction scale.

Sometimes, selling to enterprise really is the right move. The key? Evidence over ego. Paid pilots over promises. And never, ever betting your last 11 months of runway on a sample size of one.

And then, Frivolous Thoughts:

* JDM finally finds his new EDC backpack (the near-perfect Simon Sinek Optimist bag from Solgaard).

* Cameron shares his Sacramento theater adventures with some unexpected horror movie tie-ins.

As always, thanks for listening.

—Cameron and JDM

Hey friends 👋

We’re coming up on 75 episodes (yes, we’re calling that a win), and this week we’re tackling the decision every founder faces: should you pivot, persevere, or pack it in?

It’s easy to confuse “hasn’t worked yet” with “never going to work.” But the difference between those two things is where smart founders separate themselves from the pack.

We break down the evidence-based framework for making these calls. Not the hustle culture “never quit” nonsense, and not the “fail fast” hand-waving either.

The real question is when should you go all in, and when should you cut your losses while you still have resources left?

Then we put it to the test with three realistic scenarios: an AI cold email tool competing with ChatGPT, a freelancer management platform debating focus, and a social book app burning through runway with no revenue model—and, yeah, we had thoughts on that one!

For each startup, we rate them on our conviction scale and show you exactly what evidence we’re looking at. Think of it as strength training for your decision-making muscles.

Seth Godin nailed it in The Dip: winners don’t win because they never quit. They win because they quit everything else and go all in on the right thing.

Frivolous Thoughts:

* JDM discovers a criminally underrated Muppets show from 2015

* Cameron reveals the surprising origin story behind Claude AI’s name…and it deserves a podcast by itself.

As always, thanks for listening.

—Cameron and JDM

Hey friends 👋

This week we’re tackling one of the hairiest questions in early-stage startups: when do you stop doing everything yourself?

JDM’s calling in from 30,000 feet (but not really), and we dove deep into the psychology behind premature delegation. You know the pattern: founder gets scared of sales calls, hires a “head of sales” at 28 customers, then wonders why growth stalls.

We break down the progression from founder-only → founder-led → founderless work. And… most jobs need to stay in founder mode WAY longer than you think. Because you’re not just selling or building—you’re gathering evidence about what actually works.

Delegate too early and you speed up your burn while slowing down your learning.

We put three startups through our conviction scorecard. One founder was “focusing on product and vision” (red flag alert) while their sales guy closed deals and engineers built whatever customers asked for. Yikes.

Another had both co-founders deep in the trenches, documenting processes before hiring. Night and day difference.

The episode gets spicy when we make Claude generate revenue numbers in real-time for a marketplace startup, and Cameron calls out JDM’s bias.

Plus, frivolous thoughts: JDM’s master plan to game toddler psychology with wheeled luggage, and Cam mourns another Kings losing streak.

—Cam and JDM

Hey friends 👋

This week we’re tackling something we see constantly in pitch decks: impressive growth charts that hide their broken unit economics.

We dive into the real math behind customer acquisition cost (CAC), lifetime value (LTV), and payback periods—and why your revenue numbers might be hiding a ticking time bomb.

Our core question: If you stopped acquiring customers tomorrow, would your existing customers actually pay back what you spent to get them? Or are you just scaling debt?

We break down three real scenarios (okay, realistically contrived):

* A coffee subscription bleeding money on every box

* A B2B SaaS company betting everything on year-two renewals

* A meal planning app in “land grab mode” (our response: 🤯😤)

The pattern we keep seeing is a founder focusing on MRR growth while ignoring the fact that each customer costs more to acquire than they’ll ever pay back. That’s not growth—that’s buying your way out of business.

We get into the weeds on cohort analysis, retention curves, and why “brand awareness” is usually code for “we haven’t figured out profitable acquisition.” Plus, JDM does actual math in real time. It gets messy, but that’s the point… you get to hear exactly how we process these numbers (perfect for an audio podcast 🙃).

In Frivolous Thoughts:

* JDM confesses his addiction to productivity gadgets served up by an eerily accurate algorithm

* Cam discovers the joy of supporting artists through Patreon.

As always, thanks for listening.

—Cameron and JDM

Hey friends 👋

This week we’re tackling something every founder obsesses over but few actually understand: burn rate and runway.

But we’re going way deeper than just how many months you have left.

Runway isn’t just a countdown clock. It’s actually about what you’re buying with every dollar you burn. Are you learning? Growing? Building infrastructure that matters? Or just... burning to feel productive?

The episode gets real when we throw down three startup scenarios and rate them on our conviction scale. One’s spending $85K/month with only $18K in MRR (yikes). Another’s blowing $28K/month on Facebook ads in a single city. The third? Actually seems to have figured something out.

We break down why team size against customer count matters, why “investing in growth” often means “gambling on growth,” and how to think about your next major milestone in terms of evidence, not just revenue targets.

Plus, we get into the distinction between default alive and default dead—because where you land on that spectrum changes everything about how you should be spending.

And, of course, we have frivolous thoughts: JDM discovers a Lord of the Rings fitness challenge (walking from the Shire to Mordor), and Cameron explains why loan data is called “tape.”

—Cameron and JDM

Hey friends 👋

Ever had a customer ask for a feature and felt that immediate pressure to say yes?

This week, we’re tackling something every founder faces: the difference between scope creep disguised as customer validation, and high-conviction feature development.

We break down why customer requests aren’t always worth building, even when they come from your biggest accounts.

The stakes?

It’s not just wasted time and money—you’re building technical debt that turns your nimble pirate ship into a slow-moving container ship. Every feature you add based on weak signals makes it harder to pivot when you need to.

Through three real-world scenarios, we show you exactly how to evaluate feature requests. We dive into what separates “nice to have” from “urgent pain point,” and why you need to move customers from *saying* they want something to actually putting resources behind it.

The key: look for patterns, validate willingness to pay, and understand if you’re solving a real bottleneck—or just being nice.

Our conviction scale ratings ranged from “absolutely not” to “get an LOI first”—and we explain exactly why.

Plus in Frivolous Thoughts: JDM’s quest for the perfect backpack and Cameron’s love for “The Pitt” on HBO Max.

As always, thanks for listening!

—Cam & JDM

Hey friends 👋

We’re kicking off 2026 with a reality check that could save you months of wasted effort: getting amazing feedback from users means nothing if they can’t sign the check.

In this episode, we dive into the critical difference between users (who love your product) and economic buyers (who actually pay for it). This is where most B2B founders burn precious time—running pilots with enthusiastic users while completely missing the person who controls the budget.

We break down the ecosystem of pain and why the person using your solution might experience completely different problems than the person purchasing it. Just because your Slack bot saves a product manager hours every week doesn’t mean their VP will pay $750/month for the team.

Through our game format, we evaluate four real-world scenarios from compliance training platforms to AI code review tools. You’ll see exactly how we assess whether founders are validating with the right people or just collecting feel-good feedback that leads nowhere.

Key insight: If your pilot doesn’t involve the economic buyer from day one, you’re prioritizing making it work over making it sellable.

That’s fundamentally backward.

We also talk about the “four asks” framework, paid pilots vs. free trials disguised as validation, and why “saving time” is usually a weak value prop (it’s what that time unlocks that matters).

In Frivolous Thoughts, Cameron shares his new vinyl collection journey and how it’s changing the way he experiences music, while JDM recommends the sharp writing and cinematography of “Wake Up Dead Man” on Netflix.

Thanks for spending another week with us. Time is the one resource you never get back.

—Cameron and JDM

Hey friends 👋

Can you believe this is our last episode before 2026?

(We feel like we’re aging in dog years over here.)

Since everyone’s buying gifts on marketplaces right now, we figured—why not talk about the business of marketplaces? Specifically, the #1 killer of early-stage marketplace startups: lack of liquidity.

This is what most founders miss: a marketplace only exists to make transactions more efficient. That’s it. If you don’t have buyers and sellers who actually want to do business together, there’s nothing to optimize.

No efficiency = no marketplace.

We break down what liquidity actually means and why it matters more than your tech stack or your fancy matching algorithm.

Then we dive into three real-world scenarios—a handyman marketplace, a fractional sales consultant platform, and a video editor marketplace. We rate each one live on our conviction scale, pulling apart completion rates, transaction volumes, and the dreaded “managed service” red flag.

And then sh*t gets weird… JDM gets surprisingly generous with his holiday spirit ratings while Cam channels full Scrooge energy.

In Frivolous Thoughts: JDM splurges on a cinema-grade camera for his “little entrepreneurship videos” (sure, buddy), and Cam gets a sunrise alarm clock that might actually help him wake up like a human.

See you in the new year!

—Cameron and JDM

Hey friends 👋

This week we’re diving into the metric that separates high-conviction founders from everyone else: time-to-customer (TTC).

Most startups die slow deaths because they’re testing the wrong things at the wrong time.

* They spend 12 weeks building a marketplace platform when they could validate demand in 12 days.

* They build elaborate paywalls when a simple conversation would tell them if anyone will pay.

We break down why TTC is really about the pace of learning: the faster you get validated data back from actual humans willing to part with actual money, the faster you de-risk your startup.

It’s not about building faster—it’s about testing smarter.

This week, JDM and Cameron walk through three contrived (but painfully realistic) scenarios: a B2B SaaS company planning an 8-week feature build before talking to customers, a marketplace building for 12 weeks before getting both sides on board, and a freemium app that waited way too long to test pricing.

The pattern? Founders who front-load feasibility (”can we build it?”) instead of desirability (”will anyone actually pay for it?”).

And, yeah… the order matters.

We also get into the weeds on rapid prototyping, fake door tests, concierge MVPs, and why you should almost never spend months building something before getting it in front of customers.

Plus, why 200 free users might actually be worse than zero users.

And in Frivolous Thoughts—JDM nerds out over a slow-burn Scottish cop show while Cameron drops a bomb about how the University of Utah just turned college sports into a $500M private equity play.

As always, thanks for listening.

—Cameron and JDM