Feel the Boot delivers advice and experience to entrepreneurs, helping them create and grow successful businesses. We help founders go from overwhelmed entrepreneur to successful CEO.
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May 19, 2026Episode 1319 min
Friends & Family Round: How to Protect Your Relationships AND Raise Money
The friends and family round is how most founders raise their first capital — but it's also where the most relationships get damaged. If you don't structure it right, you can accidentally screw over the people trying to help you, torpedo your next funding round, and make every family gathering awkward for years.In this episode, I break down exactly how to talk to your friends and family about investing, how to structure the deal using a SAFE (Simple Agreement for Future Equity), and the ethical responsibilities you have when your investors trust you more than they understand the deal. Plus, I'll give you a tool you can send directly to your prospective investors that explains everything they need to know — from someone with no conflict of interest.Whether you're pre-revenue, pre-product, or just trying to figure out how to ask your parents for startup capital without ruining Thanksgiving, this episode has you covered.LinksBlog post: https://ftb.bz/131B YouTube: https://ftb.bz/131V Free Startup Fundraising Toolkit: https://ftb.bz/raise-yt Video to share with your F&F investors: https://ftb.bz/friends-and-family-explainer Y Combinator SAFE templates: https://www.ycombinator.com/documents
April 14, 2026Episode 13047 min
How to Build a Go-to-Market Engine That Makes Investors Pay Attention — with Javier Lozano Jr.
Most founders are doing "random acts of marketing" — a little LinkedIn, some ads, a blog here and there. Trying to be everywhere, succeeding nowhere.Javier Lozano Jr. was the CMO at Wrapmate during their run from ~$1M to over $20M in revenue and a $16M raise. His fix was counterintuitive: do less. Find the one channel showing signals, go all in, and master it before adding anything else.In this episode, Javier talks about changing one variable that took their ideal customer profile hit rate from 15% to 95% on the same budget — and how his team used "narrative engineering" to build the credibility trail that made their raise possible months before they needed the money.Show notes and full transcript: https://ftb.bz/130BWatch on YouTube: https://ftb.bz/130VYTFree Fundraising Toolkit: https://core.feeltheboot.com/raise?utm_source=podcast&utm_medium=audio&utm_campaign=organic_content&utm_content=ep130Subscribe to BootPrints: https://ftb.bz/join-p
March 24, 2026Episode 12944 min
Your Product Won't Speak for Itself — Why Technical Founders Get Overlooked | Shayna Davis
Most technical founders think their product will do the talking. It won't.Shayna Rattler-Davis has spent 15+ years helping leaders at companies like IBM, L'Oréal, and dozens of STEM startups learn how to show up with credibility in high-stakes environments. She hosts The Influence Economy Podcast (top 3% globally) and works with technical founders who are brilliant at building but struggle the moment they have to represent their company externally.In this conversation, we dig into:The competency gap most technical founders don't realize they haveWhy investors bet on leaders, not products — and what they're actually looking forHow to develop your leadership identity before you start raisingThe difference between thought leadership and just reciting your feature listWhere to start if you have zero public presence and a fundraise on the horizonThe mistakes founders make when trying to project credibility they haven't built yetA dead simple weekly exercise your whole founding team can start todayShayna drops a story about watching 24 people on tech panels in a single day and only ONE who didn't need help. If that doesn't make you question how you're showing up externally, nothing will.📋 Get Shayna's free insights report on leadership identity, branding, and messaging for technical leaders: https://techinfluence.us🔗 Connect with Shayna on LinkedIn: https://www.linkedin.com/in/shaynarattler/🎬 Watch this episode on YouTube: https://ftb.bz/129V📝 Read the full blog post: https://ftb.bz/129B🛠️ Free Fundraising Toolkit — Investment Readiness Scorecard, Validation Blueprint, Pre-Seed Valuation Guide, and more: https://ftb.bz/raise
March 3, 2026Episode 12855 min
Hockey Enforcer to $110M: Dave Burnett on Grit, Time, and Making AI See Your Startup
Former hockey enforcer Dave Burnett took punches for a living, then helped build Achievers.com (sold for $110M), watched his own business go to zero twice, and came back both times. In this episode, we dig into why founders with non-traditional backgrounds often outperform the textbook startup playbook, how to make sure AI models actually know your startup exists, and a time management system built around 1,440 minutes that will change how you think about your day. CHAPTERS0:00 Intro0:32 Dave's path from hockey enforcer to serial entrepreneur1:36 Building Achievers.com and the $110M exit3:08 Why non-traditional founders have an edge3:52 The enforcer mentality and entrepreneurial grit7:05 Building for the future: swappable AI engines8:25 AI models are commodities, not loyalties10:30 AI is table stakes now10:43 The dumbbell theory: where to build in the age of AI15:53 AI visibility: does ChatGPT, Claude, or Gemini know your startup exists?19:47 What separates visible companies from invisible ones21:00 How to use LLMTel to check your AI visibility23:01 What early-stage founders should do now to show up in AI25:18 GEO vs. SEO: what's different, what's the same26:48 Mid-roll break27:09 The 1,440-minute time management system31:04 Color-coding your day in 10-minute blocks32:23 Constraint-based prioritization: always work on the bottleneck34:36 Embracing uncertainty and getting comfortable with failure36:23 Building things nobody wants (and how to avoid it)38:27 Why Dave went so granular on time tracking40:51 Surviving a traumatic brain injury while running multiple companies41:51 Notifications are other people's priorities46:54 It's going to suck, and that's normal47:59 When to pivot vs. when to double down50:23 Going to zero twice: Great Recession and COVID53:03 Business as an infinite game55:01 Closing thoughts 🔗 LINKS & RESOURCES Dave Burnett's AI Visibility Tool (LLMTel): https://llmtel.comDave's Digital Marketing Agency: https://aokmarketing.comDave's Book "From Bricks to Clicks": https://aokmarketing.com/bookDave on LinkedIn: https://linkedin.com/in/davebburnett 📥 FREE FUNDRAISING TOOLKIT Grab templates and tools I built for the founders I coach: https://feeltheboot.com/raise 🎬 Watch the video version of this episode: https://ftb.bz/128V📖 Read the full blog post: https://ftb.bz/128B ABOUT FEEL THE BOOT Feel the Boot helps early-stage startup founders navigate the fundraising process. Whether you're preparing for your first pre-seed round or struggling to close a seed raise, we cover the strategies, frameworks, and mindset you need to raise capital and build a fundable company. Hosted by Lance Cottrell, angel investor and president of North Bay Angels. Subscribe and follow Feel the Boot wherever you listen to podcasts for episodes on startup fundraising, pitch decks, investor outreach, financial modeling, and founder strategy.
February 10, 2026Episode 12729 min
The 4 Filters: Why You Aren’t Fundable... Yet
Most founders think fundraising fails because of "bad luck." Usually, it fails because of simple physics.Fundraising is a sales funnel. If you have a structural leak at the top, no amount of "slick" pitching will produce a check at the bottom. In this episode, we pop the hood on pre-seed fundraising to look at the four filters your startup must pass before you even think about building a deck.Stop the "Fundraising Theater" and start building a machine that investors actually want to buy.Read the full blog post: https://ftb.bz/127BWatch the video: https://ftb.bz/127V[FREE TOOL] THE INVESTMENT READINESS SCORECARDDon't guess if you’re ready. Use the same diagnostic tool I use to screen startups for the North Bay Angels. Identify your gaps and fix them before you waste your one "bite at the apple."Get the Toolkit & Scorecard: https://www.FeelTheBoot.com/raiseWHAT WE COVER:Filter 1: The Math (Portfolio Physics): Why a "nice" business isn't always a venture-investable business. We look at the $100M revenue requirement and the "Why Now" delta.Filter 2: The Evidence (Market Pull): The difference between "that’s a good idea" and "I need this now." We discuss unit economics and why $1 of marketing must generate $2 of net profit.Filter 3: The Moat (Structural Defensibility): Why being a "first mover" is often a disadvantage and how to build friction that stops well-funded predators from crushing you.Filter 4: The Machine (Founder-Market Fit): Why investors don't fund science experiments and how to prove you have the unique insight to execute your blueprint.TIMESTAMPS:0:00 The "Fundraising Theater" Trap1:30 Why 99% of Success is Decided Before the Pitch3:15 Filter 1: The Harsh Math of Venture Capital5:45 The "Corpse Audit": Why Timing is Your Delta8:10 Case Study: The "Empty Box" Pitch at North Bay Angels11:20 Filter 2: Proving Customer Hunger14:45 Filter 3: Defensibility & The First-Mover Fallacy17:30 Filter 4: The Machine & Unique Insights20:15 Is Your Startup Default Alive or Default Dead?22:00 Your Next Step: The Readiness ScorecardABOUT FEEL THE BOOTI’m Lance Cottrell. I’m a former astrophysicist and successful tech founder turned startup advisor. I view company building as an engineering problem with solvable mechanics. No fluff. No hype. Just the hard truths you need to reach escape velocity.Subscribe for more pragmatic startup advice: [Link to your channel]#PreSeedFundraising #StartupFunding #VentureCapital #AngelInvestors #PitchDeck #Entrepreneurship #FounderTips #FeelTheBoot
January 23, 2026Episode 1266 min
The Investor Warm-Up Protocol: How to Turn Cold Investors into Warm Leads
If your first interaction with an investor is asking for money, you have already lost.Cold pitching investors has a success rate of nearly 0%. Warm introductions have a success rate of over 50%.The gap between those two numbers is where most fundraising rounds die.Most founders think they are stuck because they don't have a rich uncle or a deep network. The reality is: You just have the wrong process.In this episode, I break down the Investor Warm-Up Protocol, a 4-step engineering approach to manufacturing warm relationships from cold contacts. Read the full breakdown on the blog: https://ftb.bz/126B Watch The Video: https://ftb.bz/126V 🚀 RESOURCES & NEXT STEPS1. The Deep Dive (Workshop Recording):This episode is adapted from my full 90-minute workshop, "From Cold Outreach to Capital." It covers the entire system, including target list building, email scripts, and automation tools.👉 Get the Workshop: https://FounderQuest.com/cold-outreach2. The Full System (Founder Quest Intensive):Want to rebuild your entire fundraising stack (Model, Narrative, and Outreach) with hands-on coaching? Join the next cohort of the Founder Quest Intensive.👉 Apply here: https://FounderQuest.com/intensiveIn this episode, we cover:· The Radar Ping: How to become "familiar" before you ever send an email.· The "Quick Question": The specific type of DM that gets a reply (and what gets ignored).· The Update Loop: How to automate trust-building over time.· The Trap: Why pitching on the first call kills the deal.#startup #fundraising #venturecapital #founder #entrepreneurship
November 20, 2025Episode 1251 hr 3 min
The Super Connector System: David Homan on Building Relationships at the Speed of Trust
🛑 Stop Networking! Build Trust and Community to Fund Your Startup | David HomanAre you an introverted founder struggling to raise capital? Do you find most networking events to be a waste of time and purely transactional? Super connector, author, and composer David Homan reveals the systematic, high-integrity approach to connection that actually opens doors to investors, partners, and key advisors.In this powerful episode, David dismantles the myth that extroverts are the best connectors. He explains why your ability to listen deeply and build relationships at the speed of trust is your most valuable asset, turning the loneliness of the founder journey into a strength. You'll learn the crucial difference between building a transactional network and a supportive community. 🔑 Key Lessons You Will Learn:· The Introvert's Advantage: Why deep listening and high-quality, intimate connections beat "spray and pray" networking every time.· The Non-Ask Strategy: How to talk to investors before you need money to build momentum and let them experience FOMO.· Reputation Capital: The true cost of a bad introduction and why you must "honor the chain of connections" to protect your most valuable currency.· The Impact Ask: A systematic way to frame your requests to potential partners or investors so they immediately recognize how they can help.· Community Security: The high cost of opportunism and the strict rules required to filter out toxic, low-integrity contacts from your inner circle. 🔗 Resources & LinksFind the full transcript and blog post here:👉 https://ftb.bz/125BWatch the video:🎥 https://ftb.bz/125VConnect with David Homan: https://orchestratedconnecting.com/ 🚀 Struggling to Raise Capital?If you are a founder who needs checks now and hasn't built that network yet, don't worry. Learn the proven, systematic steps for warming up cold connections and securing investment directly:Cold Outreach Workshop for Founders:🔥 https://FounderQuest.com/cold-outreach#DavidHoman #FeelTheBoot #Founder #Startup #VentureCapital #RaisingCapital #Entrepreneurship #SuperConnector #RelationshipBuilding #Introvert #SEO
August 26, 2025Episode 12410 min
124. The 6 Startup Pitches Every Founder Needs
The 6 Startup Pitches Every Founder Needs Most founders only create one pitch deck, and it costs them investors. In this video, I’ll show you the six pitches every startup founder needs to win funding. From your 3-minute competition pitch to your self-guided deck for investors to read on their own, each version has a specific purpose. Skip one, and you risk losing the deal. You’ll learn:✅ Why different contexts demand different pitches✅ The right length and structure for each type of pitch✅ How to avoid the common mistake of using the wrong deck at the wrong time✅ How to build a self-guided deck that actually gets read By the end, you’ll know exactly how to tailor your message whether you’re on stage, in a meeting, or in an investor’s inbox. 📌 Want to go deeper? Join my Pitch Deck Alchemy workshop for a 90-minute masterclass on designing a deck that gets you funded: https://founderquest.com/pitch-deck-alchemy Read the Blog: https://ftb.bz/124B Watch the Video: https://ftb.bz/124V
July 11, 2025Episode 12310 min
123. Founder/Market Fit: Your Startup’s Early-Stage Advantage
Founder/Market Fit: Your Startup’s Early-Stage Advantage Stop guessing about “Founder–Market Fit.” In this episode I break down how investors spot it at the pre-seed stage— and what to do if you don’t have it yet. When founders enter a market they’ve never lived, credibility gaps, weak insight, and scarce access can stall everything from customer discovery to fundraising. I’ll show you:What “Founder–Market Fit” really means and why VCs look for it before they fundClear warning signs you don’t have it (yet)Practical moves to build or borrow the fit you needHow great FMF accelerates product-market fit, hiring, partnerships, and Series A readiness Whether you’re raising your first round or refining your pitch, use these ideas to turn experience into a strategic edge. 🔗 RESOURCES & NEXT STEPS Blog article & full transcripthttps://ftb.bz/123B The Feel the Boot Videohttps://ftb.bz/123V Free founder community — The Crossroadshttps://ftb.bz/crossroads Fundability Quiz — Are you really ready to raise?https://ftb.bz/fundable
June 19, 2025Episode 12212 min
122. How Founders Sabotage Themselves with ChatGPT
Are you outsourcing your thinking to ChatGPT? That’s a fast track to sabotaging your startup. In this episode, I share two real conversations I had with founders who said they got their market size numbers from ChatGPT. That is a red flag for any investor. The problem is not that they used AI. The problem is that they didn’t understand what the answer meant or where it came from. I walk through the right and wrong ways to use tools like ChatGPT in your startup. Whether you’re researching your target market, writing content, or creating your financial projections, you need to know what is solid and what is just noise. You will learn:· When using AI makes sense and when it is a trap· How to ask for citations so you can verify the data· Why AI-generated financials almost always fall apart· What to do instead so you can sound sharp and raise with confidence This isn’t about avoiding AI. It is about using it well so you can think clearly, move faster, and make better decisions. 📍 Join The Crossroads Founder Community: https://ftb.bz/crossroads📊 Take the Fundability Quiz: https://ftb.bz/fundable🎙 Listen to the Podcast: https://ftb.bz/podcast📝 Read the Blog: https://ftb.bz/122B
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