How To Founder

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 fail...

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 roun...

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 is...

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...

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...

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 cel...

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 t...

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 infrastructur...

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...

What if your org chart is actually lying to you? Those neat boxes and reporting lines suggest work flows predictably from one function to the next. But watch what happens when a customer complaint lands. It bounces between departments while everyone optimizes for their own metrics. The customer waits. The system fails. In this episode, we sit down with Todd Hagopian, author of  The Unfair Advantag...

Your marketing team hit their numbers. Your sales team says the leads are trash. Both are right, and that's the structural failure you built. In this episode, Jon Ferrara, founder of Goldmine and Nimble, reveals why the marketing-sales war isn't a people problem. It's a compensation problem. Marketing gets bonused on MQLs. Sales gets bonused on closed deals. The gap between those metri...

You've known for months. The employee who was great in year one but can't grow with the company. The customer who's been with you since the beginning but costs more to serve than they pay. The prices you set when you were desperate that no longer make sense. You know what you should do. But knowing isn't the hard part. The hard part is that you actually care about these people. You...

What if the skills that made you successful are now holding your company back? Rand Fishkin built Moz to 150 employees before admitting he'd become the company's biggest bottleneck. His mistake wasn't incompetence. He kept doing the job that worked at fifteen people. In this episode, we map the specific shifts required at each growth milestone. What behaviors to abandon. What new muscl...

Your pipeline is lying to you. A sales coach tracked a client's team for ninety days and found forty percent of their pipeline would never close. Those zombie deals weren't just dead weight. They were stealing attention from the fifteen percent that could actually convert. Most founders treat every lead like a lottery ticket, terrified that the one they disqualify might have been the big w...

You're staring at the decision: hire your first person or stay solo. Everyone says you need a team to scale. But what if they're wrong? Jason Cohen ran SmartBear Software solo at seven figures and turned down acquisitions because staying solo was his competitive advantage. This episode isn't about choosing the "right" path—it's about understanding you're choosing betw...

What if your alignment meetings are just expensive procrastination? Jared Christopher built Yellowfin BI's sales team to 340% revenue growth in two years without a single alignment meeting. Each regional director had complete authority with one rule: defend your decisions with data. While competitors held stakeholder sessions, Yellowfin shipped. In this episode, Blima Ehrentreu, founder and CE...

What if paying people to show up is the problem? Joey Rockey has built 29 businesses, with 25 now running without him. His secret isn't better delegation or time management. It's designing businesses where employees get paid for results, not hours. Hotel housekeepers who finish by noon and earn more than hourly workers. Marketing teams compensated per customer acquired who iterate in real...

Most founders think organizational design is something you do once you're big. Wrong. Your company already has structure. Communication patterns exist. Informal networks formed the day your second employee started. The only question is whether you designed it or it designed itself. Chris and Stephanie break down when structure helps versus when it kills momentum. They explore why startups fail...

What if the most unethical thing you do in sales is refuse to apply pressure? Most founders avoid psychological triggers in sales because they feel manipulative. The result? Prospects drown in information, freeze in indecision, and walk away from solutions they genuinely need. The discomfort founders avoid creating is often the service prospects desperately require. In this episode, Wes Schaeffer,...

What transforms a lone visionary into the leader of a movement? In this episode, Chris and Anthony unpack the first follower principle and reveal what early believers are actually buying when they choose to follow you. Spoiler: it's not your product, your pitch, or even your vision. It's the identity upgrade they get from being first. You'll discover why Infusionsoft's early custom...

Eighty-four percent of B2B sales start with a referral—so why are most founders still waiting for them to happen naturally? In this episode, Brandon Barnum, CEO of HOA.com and author of Raving Referrals, reveals the system that turns referrals from occasional windfalls into predictable pipeline. Discover why asking for referrals at the beginning of a relationship (not the end) changes everything,...

What if everything you've been told about burnout is wrong? In this raw and revealing episode, hosts Anthony Franco, Chris Franks, and Stephanie Hayes dismantle the traditional definition of founder burnout. It’s not just about working too hard—it’s about a dangerous misalignment between your energy and your vision. Discover why "rest" might be the wrong prescription, how the "P...

What if that "non-dilutive capital" just put your house on the line? Most founders think equity is their only option, but 73% of businesses seeking financing actually apply for loans. The gap isn't about availability—it's about understanding what you're signing up for. In this episode, we break down SBA loans, personal guarantees, convertible debt, factoring, and the brutal t...

Why do some founders get replies from total strangers while your emails get ignored? Research from Boomerang analyzed five million emails and found messages between fifty and one hundred twenty-five words get the highest response rates. Yet most founders either write novels or fire off three-sentence pitches. When one founder launched his SaaS product, he built his early customer base through cold...

Founders spend an average of fourteen months running a business they know is dying. Why? In this raw, unfiltered episode, Anthony Franco opens up about the collapse of MC Squares—a company doing four hundred thousand in monthly revenue that imploded after an Amazon glitch tanked sales by fifty percent overnight. Stephanie Hays shares her battle with a zombie company: profitable, stable, loved by c...