Claim OwnershipHow To Founder
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© Anthony Franco
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Founders are pioneers of economic prosperity. We equip them for the journey.
Think you know the real story of entrepreneurship? Think again. "How to Founder" dives headfirst into the messy, often unspoken realities of building a business. We're not here for the typical success stories; we're challenging conventional wisdom, tackling tough topics, and giving you the unfiltered truth about what it actually takes to succeed. If you're ready to move beyond the status quo and are looking for a podcast that's as ambitious as you are, subscribe now. It's time to rewrite the rules and build your own
Think you know the real story of entrepreneurship? Think again. "How to Founder" dives headfirst into the messy, often unspoken realities of building a business. We're not here for the typical success stories; we're challenging conventional wisdom, tackling tough topics, and giving you the unfiltered truth about what it actually takes to succeed. If you're ready to move beyond the status quo and are looking for a podcast that's as ambitious as you are, subscribe now. It's time to rewrite the rules and build your own
167 Episodes
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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 between two different games. Solo gives you freedom, speed, and full control. Teams give you leverage, collaboration, and the ability to build beyond yourself. Both can win. But you can't play both games at once. We break down the real trade-offs, the systems solo founders need to scale, why the worst hire is your first one done too early, and how to know which ceiling you're actually optimizing for. This is permission to choose your constraint consciously.Keywords: solo founder, hiring decisions, business models, founder constraints, scaling strategies, team building, entrepreneurship trade-offs, founder freedom, growth decisions
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 CEO of The Designers Group, breaks down the difference between collaboration and consensus, why transparency has limits, and how to create psychological safety without sacrificing decision velocity. You'll learn when to gather input, when to make the call, and how to build values into your hiring process instead of your wall.If you're stuck in meeting hell or wondering why your team feels slow, this episode will show you how to move faster without burning trust.Keywords: decision-making, team alignment, psychological safety, startup leadership, company culture, decision velocity, team management, founder advice
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 time. Line cooks paid on attendance and quality ratings who batch tasks for efficiency.This episode breaks down how to structure every role for performance-based pay, why it filters for the right people during hiring, and how it eliminates the micromanagement trap that keeps founders stuck. Discover why most businesses fail to run independently, what changes when you stop rewarding time, and how to build systems that work better when you're not there.Keywords: commission-based compensation, performance pay, business automation, building sellable businesses, eliminating micromanagement, founder independence, systems design, hiring for results
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 by copying big company org charts, what happens when you hire managers too early, and how to build around accountabilities instead of people. Learn why flat hierarchies create bottlenecks, how to map the real communication patterns in your business, and when teams beat departments.If you're adding your third employee or your thirtieth, you're doing organizational design whether you realize it or not.Keywords: organizational design, startup structure, team building, management hierarchy, accountability framework, communication patterns, business growth, org chart design, flat hierarchy
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, known as "The Sales Whisperer," breaks down why the old information advantage is dead. Buyers now arrive with hours of research and paralysis to match. The modern salesperson's job isn't delivering information. It's helping people make decisions by asking questions they haven't rehearsed and matching how they sell to how prospects actually buy.You'll learn why bad scripts give all scripts a bad name, how to break prospects out of their defensive armor, and why humanity might be the next killer app in an increasingly automated world.Keywords: sales psychology, psychological triggers, closing sales, sales training, founder sales, Wes Schaeffer, Sales Whisperer, buyer psychology, decision making, sales techniques
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 customers weren't buying software but buying proof they were "real marketers." You'll learn the difference between the Forrest Gump approach to building followers (just be so visionary people show up) and the tactical approach (manufacture the movement), and why neither works alone. And you'll understand why authenticity isn't optional: manufactured personas collapse when flaws surface, while honest vulnerability creates durable followings.Whether you're trying to attract your first customer, your first investor, or your first employee, this episode reveals what makes someone genuinely followable.
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, how to automate referral requests so they happen without you remembering, and why seventy-nine percent of business owners have virtually zero strategic referral partners—and how to build a network that actively fills your calendar. This is the infrastructure that replaces cold outreach with warm introductions.Keywords: referrals, B2B sales, referral partnerships, sales process, Brandon Barnum, business development, lead generation, sales strategy
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 "Practitioner's Paradox" is secretly capping your revenue, and why being a strategic underachiever might be the smartest move you can make. The team shares personal battles with the "overcommitment trap" and reveals the counterintuitive mental hygiene habits that keep successful founders in the game.Keywords: founder burnout, startup psychology, mental health for entrepreneurs, scaling challenges, business strategy, productivity myths, leadership alignment, Anthony Franco, Chris Franks, Stephanie Hayes
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 truth about when debt accelerates your business versus when it destroys everything you've built. Discover why your EBITDA matters more than your assets, how customers can be your best source of capital, and the one question every founder must ask before signing a personal guarantee. This is the financing conversation nobody had with you before you needed it.Keywords: debt financing, equity financing, SBA loans, personal guarantee, startup funding, convertible debt, factoring, business loans, EBITDA, founder advice
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 email by spending thirty minutes researching each recipient before writing a single word. That investment in understanding inbox psychology turned strangers into allies who wanted to help.In this episode, globally recognized networking expert Lirone Glickman breaks down the exact four-line structure that turns cold emails into conversations, the know-like-trust sequence that warms relationships before you ask for anything, and why ending with a question mark instead of a period increases response rates by twenty percent. Discover the mindset shift that makes outreach feel less like begging and more like offering value, plus the common mistakes that guarantee your email gets deleted.Keywords: cold email strategies, networking tips, business outreach, email response rates, Lirone Glickman, founder networking, relationship building, sales outreach
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 customers, but trapped in limbo with misaligned partners. Together, we break down the two types of business closures, the brutal mechanics of bankruptcy, and why founders suffer alone when they don't have to.This conversation doesn't sugarcoat the shame, the financial wreckage, or the mental health toll. But it also reveals what happens on the other side—and why closing a business isn't failure, it's survival.Keywords: business shutdown, startup failure, bankruptcy, zombie company, founder mental health, business closure, failing business, entrepreneurship challenges
You sold your company. The wire cleared. Six months later, you're more anxious than when you were working 80-hour weeks.Most founders spend years planning their exit strategy and zero hours planning what happens the day after the deal closes. Tom Freiling led a digital publishing company to NASDAQ, sold it, then launched into his next venture without taking a breath. Looking back, he calls it his biggest mistake. The problem wasn't that he kept working. The problem was he never figured out who he was outside the company he'd just sold.This episode breaks down the post-exit transition most founders get wrong. We explore why your anti-portfolio matters more than your vision board, how to structure strategic downtime so it doesn't become purposeless drift, and why the best thing you can do after an exit is help other founders while you figure out what comes next.Keywords: exit strategy, post-exit planning, founder identity, second venture, entrepreneurship transition, Tom Freiling, strategic downtime, anti-portfolio
Your benefits broker just bought a boat. You paid for it.Mid-size companies waste an average of eighteen hundred fifty six dollars per employee annually on hidden broker fees their advisors never disclose. These aren't mistakes. They're business models built on your ignorance. When your broker's compensation rises with your costs, fiduciary duty dies. They'll smile, bring donuts to enrollment meetings, and quietly collect six figures in carrier kickbacks while explaining there's nothing more they can do about rising premiums. Donovan Pyle spent years on both sides of this system, flying brokers on luxury vacations to ensure they recommended his employer's insurance products. Now he's a whistleblower exposing the three hundred billion dollar brokerage blindspot and helping companies reclaim wasted benefits dollars through fiduciary-based consulting.Keywords: employee benefits, health insurance costs, benefits broker fees, fiduciary advisor, healthcare waste, self-insurance, PEO alternatives, benefits optimization, startup benefits strategy, health benefits procurement
You bought the expensive firewall. You paid for the certifications. You still wake up wondering if one phishing email could wipe you out.Most founders throw money at cybersecurity like it's insurance against catastrophe. They stack tools, chase compliance badges, and assume more spending equals more protection. Meanwhile, the three attack vectors responsible for 82% of breaches sit wide open because they're boring to fix and nobody sells a flashy product for them.Tolulope Michael has trained over 1,000 cybersecurity professionals and worked with major companies including FedEx and Nomad Health. He's watched founders waste tens of thousands on security theater while ignoring the unglamorous fundamentals that actually stop breaches. This episode cuts through the vendor noise to reveal what founders must lock down first and what expensive "solutions" are just performance art.Keywords: cybersecurity, security theater, phishing attacks, password security, multi-factor authentication, HIPAA compliance, data breach prevention, risk mitigation, startup security, small business cybersecurity
When was the last time you made a business decision before asking what it costs in taxes?Most founders design their operations first, then call their accountant in March to calculate the damage. They hire in July, buy equipment in November, distribute profits in December, and never consider tax implications until the bill lands. Mike Jesowshek spent a decade watching entrepreneurs bleed five figures annually, not from missing deductions but from building their businesses backwards. According to the National Society of Accountants, small businesses overpay by $11,400 per year on average due to missed planning opportunities.In this episode, Mike breaks down the difference between tax preparation (compliance paperwork) and tax planning (proactive strategy that actually saves money). You'll learn why your entity structure matters more than you think, how to shift everyday spending from after-tax to pre-tax dollars, and which strategies work at $100K versus $1M in revenue. If you've ever felt like taxes are something that happen to you rather than something you control, this conversation will change how you build.Keywords: tax strategy, tax planning, S-corporation, LLC structure, small business taxes, tax deductions, entity structure, CPA advice, business tax savings, self-employment tax
What if that pit in your stomach before a difficult conversation isn't weakness—it's wisdom? Most founders think nervousness before hard talks signals they're unprepared. The reality? Zero anxiety means you're about to be too harsh or unclear. That discomfort is your nervous system telling you the stakes are real and the relationship matters. In this episode, we break down why calibrating your emotional state—finding the sweet spot between paralyzed and robotic—is the secret to conversations that build trust instead of destroying it. You'll learn when vague feedback is cowardice disguised as kindness, how to weaponize specificity without weaponizing the relationship, and why leaders who telegraph difficult conversations 24 hours ahead see double the success rates. If you've been avoiding a conversation that's quietly poisoning your team, this episode gives you the framework to finally have it.Keywords: difficult conversations, leadership communication, founder advice, performance feedback, firing employees, managing conflict, psychological safety, business communication, team management, leadership development
Why do the processes you create end up ignored? You document workflows, create templates, build systems—and then nobody uses them. The problem isn't discipline. It's design.Most founders treat processes like chores instead of products. They skip user research (who's actually using this?), ignore usability (can someone follow this under pressure?), and never iterate. Colin Gray turned this around by building The Podcast Host and Alitu using one principle: every process is a product for your future self.In this episode, discover the inflection points for documentation, how to design processes that actually get used, and why treating systems like shelf-ware kills growth. Learn the "First Use Test" that separates working processes from documentation theater, why most process metrics create worse problems than no metrics at all, and how to build systems your team actually wants to use.Stop building process graveyards. Start shipping systems that work.**Keywords:** process design, systems thinking, operational efficiency, business processes, team productivity, process automation, Colin Gray, podcast platform, Alitu
What if everything you know about authentic leadership is wrong?In this eye-opening episode, we sit down with executive coach Andrew Poles, a 3x founder who's guided over 10,000 leaders worldwide. Discover why the "authentic you" who got you here won't get you there, how elite founders rehearse their leadership character like actors prep for Broadway, and the exact moments you need to perform confidence you don't feel. We'll explore the neuroscience of performative trust, the scripts that turn micromanagers into visionaries, and why treating leadership as theater might be the most authentic thing you ever do. If you're waiting to "feel like a leader" before acting like one, your team is already looking elsewhere.Keywords: leadership development, executive coaching, founder mindset, authentic leadership, performance psychology, team management, Andrew Poles
What if the moment you finally exhale is the moment your business starts to die?This raw, unfiltered conversation between Chris Franks, Anthony Franco, and Stephanie Hays tackles the uncomfortable truth most founders avoid: success breeds complacency, and complacency breeds failure. They dissect why seventy-three percent of midsize companies plateau within three years of hitting profitability, explore the addictive nature of startup anxiety, and reveal why the most dangerous phrase in business might be "we've made it." From debating whether growth is actually essential to examining the mental health toll of perpetual hustle, this episode delivers the reality check every comfortable founder needs to hear. No guests, no filters—just three battle-tested entrepreneurs confronting the paradox that staying hungry requires intentional discomfort.Keywords: founder comfort zone, midsize business plateau, startup stagnation, entrepreneurial anxiety, business growth strategies, profitable company challenges, founder mental health, innovation versus stability
Ever wonder if you're the bottleneck in your own business?According to MIT Sloan Management Review, fifty-eight percent of executives admit their leadership approach hasn't evolved with their organization's growth stage. What worked brilliantly at five employees creates chaos at fifty. In this revealing episode, we sit down with Dr. Christiane Schroeter—TEDx speaker, top one percent podcaster, and leadership coach with a PhD in health economics—to explore how rigid leadership identities create predictable bottlenecks. Discover why self-awareness beats strategy, how to recognize when you're draining your team's energy, and why small leadership adjustments create massive organizational shifts. Whether you're consensus-driven facing rapid scaling or hands-on struggling to delegate, this conversation will challenge how you see yourself as a leader.Keywords: leadership development, founder growth, leadership styles, scaling companies, self-awareness, delegation, business growth, entrepreneurship, organizational development, team management
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