How To Founder

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 when you join an early-stage company, how to position yourself so the founder sees you as someone who takes work off their plate instead of adding to it, and why getting in sideways through people and presence beats applying through job boards. Whether you're aiming for your first startup role or leaving corporate to join something earlier-stage, this conversation reframes the search.

Keywords: startup jobs, getting hired at a startup, founder hiring, early-stage careers, startup recruitment, job search, Anthony Franco, Chris Franks, Stephanie Hayes, How To Founder

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 sets of financials (and why that's killing their fundraising chances), how to build a data room that actually works, and the counterintuitive truth about investor hygiene that starts long before you need investors.

Heidi breaks down the venture readiness framework: creating a data room that lives in the cloud, practicing investor hygiene through monthly stakeholder updates, and doing the honest math on fundraising (if you need twenty yeses, you're talking to two hundred people). But here's what most founders miss: the easiest way to get capital into your company might not be fundraising at all.

This is the financial literacy conversation founders actually need—not theory, but the daily practices that separate operators who raise money from those who just talk about it.

Keywords: financial literacy, fundraising, data room, investor relations, venture capital, startup finance, financial discipline, Heidi Knoblauch

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 why standard financial statements fail founders, how forecasting builds strategic intention rather than just prediction, and why the five-line P&L cuts through complexity. Colin shares hard-won lessons from two decades of building, buying, and turning around businesses, including his own early-career turnaround where brutal honesty about reality made the difference between survival and collapse.

Whether you're struggling to understand why profit doesn't match your bank balance or preparing your business for eventual exit, this conversation reframes how founders should think about cash, valuation, and financial literacy.

Keywords: cash flow management, profit vs cash, financial statements for founders, business turnaround, Colin Sanburg, FinElevate, startup finances, forecasting, business valuation, entrepreneurship

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, and the approaches that have employees coming back the next day with flowers.

They break down the timing calculus that founders get wrong, why stoicism becomes cruelty in this moment, and what the remaining team needs to hear immediately after. This isn't the business mechanics. It's the human experience of delivering the worst news of someone's week, and leading through it.

Keywords: layoffs, founder leadership, firing employees, team management, startup challenges, difficult conversations, employee termination, leadership skills, company restructuring, entrepreneurship

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 that yours likely doesn't, why ARR is a banned term in SEC filings, and the lethal mistake mid-market companies make that cuts their valuation in half during due diligence. Whether you're aiming for the NASDAQ buzzer or looking for secondary market liquidity without the public overhead, this episode provides the high-stakes roadmap for building a durable, audit-proof business.

Keywords: IPO readiness, Aman Verjee, revenue recognition, secondary markets, public company CFO, growth capital, exit strategy

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, we dig into the experience-versus-potential debate, exploring when credentials matter, when they backfire, and how AI is reshaping the calculus entirely. You'll learn why Wade Foster built Zapier to 600 employees without an HR department, why sales might be the last role you should hire for experience, and the two traits that predict startup success better than any resume line.

Whether you're making your first hire or your fiftieth, this conversation will change how you evaluate candidates.

Keywords: hiring for potential, startup hiring, experience vs potential, hiring mistakes, founder hiring tips, early stage hiring, startup recruiting, building teams

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 Advantage, to explore why treating your organization as a system changes everything. Todd breaks down how silos form from good intentions, why decision rights matter more than reporting structures, and how small companies can use tools like RACI charts before problems emerge rather than after. You'll learn why your best performer might be your biggest liability, how to follow the "deer trails" your team has already created, and why adding resources is almost never the answer to a dragging function.

Whether you're building your first team or untangling years of accumulated confusion, this conversation will reshape how you think about organizational design.

Keywords: org chart design, systems thinking, organizational structure, RACI framework, decision making, silos, team structure, Todd Hagopian, business systems, operational efficiency

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 metrics is a war zone you funded.

Jon spent three decades watching companies accidentally design their marketing and sales teams to fight each other. He shares the structural fixes that actually work: replacing MQLs with sales-accepted leads, aligning everyone on a single metric, and building response time accountability that turns dead leads into closed deals. You'll learn why most CRMs are built for management instead of relationships, and how to create a single source of truth that ends the turf wars.

Keywords: marketing sales alignment, CRM strategy, lead management, sales accepted leads, revenue operations, marketing qualified leads, sales team structure, Jon Ferrara, Nimble CRM, Goldmine

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 remember when they believed in you before anyone else did. You've been to their kids' birthday parties. And now leadership requires you to make a call that will hurt them.This is the crucible where founders either become leaders or stay nice people running struggling companies. Because here's what nobody tells you: the inability to make hard decisions isn't kindness. It's a form of selfishness that protects your comfort while everyone else pays the price.Today, Anthony, Chris, and Stephanie dig into the decisions you've been avoiding, the real cost of delay, and how to make hard calls without losing your humanity.

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 muscles to build. Why the ceiling you're hitting isn't about your team or your market. It's about a version of yourself that's overstayed its welcome.

We cover the brutal transition at ten employees when tribal knowledge dies, why founders retreat to operator mode when anxiety spikes, how to find people who will actually tell you the truth, and the uncomfortable reality that every growth stage demands you fire yourself from jobs you're good at.

This isn't theory. It's the playbook for founders who refuse to be the reason their company stalls.

Keywords: CEO evolution, founder growth, leadership transitions, scaling yourself, company growth stages, self-awareness, delegation, entrepreneurship, startup leadership, founder bottleneck