How To Founder

Your profit report says things are great. Your bank account disagrees. What's actually happening?

In this episode, e-commerce CFO Abir Syed breaks down the profitability paradox that quietly kills growing businesses: why strong margins and a healthy P&L can coexist with a genuine cash crisis, and how founders who don't model their cash conversion cycle find themselves on a treadmill of expensive short-term debt they can ...

In this episode, we break down what user experience actually means — and it's not what most founders think. UX isn't your app's color scheme or button placement. It's the entire chain from first contact to renewal, and every gap in that chain is costing you customers you'll never get back.

Anthony Franco, founder of the world's first UX agency, joins Stephanie and Chris to unpack the most common UX mistakes f...

You signed the papers. The wire hit your account. So why does it feel like grief?

In this episode, we dig into the emotional reality of selling your business, the part nobody prepares you for. Veronica Zora Kirin, serial founder, two-time TEDx speaker, and anthropologist, breaks down why exits mirror the stages of grief even when they go exactly right. We cover how to read the slippage signal before you've stayed too long, what ...

Every option you keep open is silently billing you.

Most founders call it flexibility. Investors call it hedging. The founders who've been through it call it what it actually is: fear dressed up in strategic language. In this episode, Anthony, Chris, and Stephanie break down the optionality trap — why the instinct to keep doors open destroys more companies than bad products ever did.

They cover how to tell the difference between ...

Your company already has a culture. You just didn't design it.

Every founder talks about building culture intentionally. But culture isn't built during the retreat or the values workshop - it accumulates in every decision you make under pressure, every behavior you let slide, and every pattern you carry into the office from your personal life. Lisa Johnson, co-founder of Been There Got Out, built her business through ten yea...

Your team tripled. Revenue doubled. And somehow, you're slower, messier, and more dependent on the founder than you were at ten people.

In this episode, Chris Franks and Stephanie Hays dig into the specific mechanisms that cause growth to break good companies. Not the obvious failures, but the invisible ones: the informal communication patterns that disappeared when you added headcount, the profile mismatches that make your best...

The habits that made you a top performer at a big company can quietly wreck your startup.

In this episode, New York Times bestselling author and entrepreneur Randy Gage joins the conversation to dissect the mental software founders carry out of corporate life, and why it's so hard to uninstall. From surrounding yourself with sycophants to building overhead too fast, the traps are predictable. So are the fixes.

You'll ...

Your support costs are hiding your biggest competitive advantage.

Most founders treat customer service as a cost to minimize. Jeff Bezos built Amazon by treating it as a failure signal. Every support contact meant something broke. Fix the contact, and you've got a satisfied customer. Fix the process that caused it, and you've got a competitive moat.

In this episode, Steve Anderson, author of The Bezos Letters, breaks down how...

What if the infrastructure protecting you from scale is the reason you can't afford to reach it?

Basecamp's founder publicly abandoned the cloud after calculating they'd spent $3.2 million annually on AWS. Their discovery? Actual usage didn't match what they were paying for. Today we sit down with Vidar Hokstad, founder of Hokstad Consulting, who's spent twenty-five years helping startups stop overengineering the...

What if the price you're charging is teaching your customers your product isn't worth that much?

Most founders treat pricing as a math problem: add up costs, slap on a margin, done. But pricing expert Dan Balcauski reveals why this approach leaves massive value on the table. In this episode, we explore why your price is actually a positioning decision that determines everything from your sales motion to your customer quality...

You built something from nothing and somewhere along the way, you became "the person who does this." Your identity fused with your company, your role, your expertise. That merger felt like commitment. It was a trap.

The sunk cost dilemma runs deeper than money or time. It's about who you've become and the terrifying question of who you'd be without it. Founders hold onto failing strategies, dead partnerships, a...

You've known for months who needs to go. The documentation feels thin. The conversation you keep rehearsing never sounds right.

In this episode, staffing CEO Bill Kasko, who built Frontline Source Group to 31 locations over 25 years, breaks down why most termination problems are actually hiring problems. He shares the single interview question that reveals more about a candidate than nine rounds of interviews, explains why firin...

You handed it off. They dropped it. But what if the problem wasn't their execution?

In this episode, Chaz Wolfe, founder of Gathering the Kings Masterminds, breaks down the difference between delegation and abdication. He's built and sold multiple seven-figure companies and interviewed over 400 entrepreneurs, and his take on why most founders fail at delegation hits different. The issue isn't finding reliable people. It&...

Why do the least qualified candidates keep getting hired at the best startups?

Wistia's founders learned their best hires weren't credentialed specialists. They were self-starters who had built something on their own without anyone asking. In this episode we break down what startup founders are really evaluating when they hire, and it's not what job boards train you for. We cover what you're actually signing up for w...

What if the secret to raising capital isn't learning complex financial models, but building the same daily discipline that kept a restaurant owner alive on two weeks of cash reserves?

In this episode, we sit down with Heidi Knoblauch, who built Plum Oyster Bar, managed $180 million in venture funds, and now helps founders develop the financial instincts they need to succeed. Discover why most founders maintain three different se...

Your most profitable month might be your most dangerous. 

In 2015, Crumbs Bake Shop reported record revenue while filing for bankruptcy. Thirty locations. Profitable on paper. Couldn't make the next lease payment. The P&L lied. The bank account didn't.

In this episode, serial entrepreneur Colin Sanburg reveals the four "cash monsters" that devour businesses while founders celebrate paper profits. He breaks down ...

What do you owe someone in the thirty seconds after you've just ended their career?

Most founders prepare the spreadsheet, rehearse the legal script, and completely miss what actually matters: sitting across from someone whose identity is tied to a job that no longer exists. In this episode, Anthony, Chris, and Stephanie share their personal experiences on both sides of layoffs, the mistakes that make a hard conversation cruel, ...

What if your "growth" is actually a liability in an audit?

In this eye-opening episode, we sit down with former eBay and Sonos CFO Aman Verjee to demystify the brutal reality of going public. Most founders treat an IPO as an exit, but Aman reveals why it’s actually the start of a punishing new journey requiring a complete architectural overhaul. Discover the "invisible infrastructure" public companies possess tha...

What if the candidate with the perfect resume is actually your worst option?

Most founders default to experience when hiring. It feels safe. But that ten-year veteran from a Fortune 500 company has been trained to operate inside systems you don't have—and may never build. They expect structure, support, and clear swim lanes. Your startup offers chaos, ambiguity, and problems that don't fit job descriptions.

In this episode, w...