How To Founder

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