Feel the Boot

I see about 1,000 startups a year and invest in one or two. Here's the real conversion rate at every stage of startup funding, from first message to wired funds.

When I ask a founder to send me their deck, there's about a 1.5% chance I'll end up writing them a check. Most founders hear "send me your deck" as a really strong statement of interest. Most investors don't want to talk about how few investments they actually make compared to the number of pitches they get.

The effort an investor puts into responding tells you how seriously to take it. A deck request takes ten seconds to type. Due diligence is real work. And even a soft circle commitment, the strongest signal short of money in the bank, only turns into a wire about half the time in my experience.

In this episode I walk through my own funnel, from 1,000 pitches to 100 deck requests to 10 real conversations to one or two checks, and why it drops to zero in years I'm not deploying capital. I cover why my numbers are a floor rather than a typical figure, and what a meeting, due diligence, and a soft circle are each really worth.

Then I get into why so many commitments fall apart even when nobody's acting in bad faith, including the angel who backed out of a million dollar commitment to me at the last instant. Why a fully soft circled round is really about half funded, and why being oversubscribed puts you in a much stronger position. And the question to ask the investor at each stage so you find out where you stand sooner.

The rule underneath all of it: don't take your foot off the gas until the money is in your bank account.

Links

Pitch Audit: I review your deck and materials, then we spend an hour on exactly what's blocking your raise. $500: https://founderquest.com/pitch-audit

Full write-up: https://ftb.bz/135B

Watch the video version: https://ftb.bz/135V

Free fundraising toolkit: https://ftb.bz/raise

The PACT from Founder Institute: https://fi.co/insight/the-pact

Bad startup advice usually comes from smart, successful, well-meaning people. That's exactly what makes it so hard to catch.

A prototype-stage hardware founder was told by a reputable investor at a large VC firm never to raise less than $5 million, which implies a valuation around $20 million. That ask would have gotten her laughed out of every investor meeting I've ever sat in. The investors I actually work with would want to see $750,000 at $3 to $4 million pre-money.

He wasn't running a scam. He was answering a question about a company that wasn't hers.

Every piece of startup advice is aimed at a specific company, real or imagined. It assumes a stage, a level of capital intensity, an opportunity size, and something about what the founder actually wants. Advisors rarely state those assumptions out loud, and most aren't even aware of them. Your job isn't to decide whether the advice is good. It's to work out what company it was built for, and whether that's yours.

In this episode I cover how that $20 million valuation would have wrecked her next round and burned her best investors, the handful of advisors genuinely worth running from, including success fees that are illegal in the US unless the person is a registered broker-dealer, and why advice from the most credible sources is the hardest to question.

Then I get into where the same mismatch shows up outside fundraising, in process, in pricing, and in technology decisions. How much scrutiny a piece of advice deserves, scaled to how hard it would be to undo. What valuation methodologies are really used for, which is not what you'd hope. And the bias built into my own videos, stated plainly, so you can discount me appropriately.

It comes down to two questions. Is this advice for you? And how hard would it be to undo?

Links

Book a first call with me, one hour, $500, refundable if we're not a fit: https://api.leadconnectorhq.com/widget/bookings/first-council-call?utm_source=podcast&utm_medium=show_notes&utm_campaign=ep134-advisors

Full write-up: https://ftb.bz/134B

Watch the video version: https://ftb.bz/134V

Free fundraising toolkit: https://ftb.bz/raise

Notes

No timestamps, no podcast link, per your instruction. Links go to blog and video only.

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Booking link carries utm_source=podcast&utm_medium=show_notes. Plenty of listeners never open show notes at all, so treat low numbers here as normal rather than as a problem with the copy.

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Investors form their first judgment about you before you've said a word about your product. At the early stage they bet on the founder, not the idea, which makes the signal you send long before the pitch one of the most important things you can control.

In episode 133, Lance Cottrell sits down with Christine Blosdale, the Expert Authority Coach, to turn personal branding into something practical for founders who are raising money. They get into why expertise so often fails to translate, how to fix a pitch deck that buries the point, and the difference between confidence and the kind of braggadocio that makes investors run. Christine shares the "crown jewels" approach to surfacing the parts of your background that actually matter to investors, and Lance connects each idea back to the pitch decks and team slides he reviews every week.

You'll also hear why your headshot and team slide quietly decide how seriously you're taken, how to handle imposter syndrome before a raise, and what it means that investors now Google and ChatGPT your name before a meeting. If you're a founder building credibility, visibility, and investor trust, this one is for you.

CHAPTERS 0:00 - Investors judge you before you say a word 1:15 - Why expertise doesn't translate: clarity over credentials 3:11 - Bet on the founder, not the product 3:45 - The media kit photo that opened doors 5:51 - Build your founder press kit (your crown jewels) 8:21 - The 10-second elevator pitch (and the $5M version) 9:32 - Confidence without the arrogance 11:49 - Imposter syndrome and the Dunning-Kruger trap 13:09 - Why great actors battle imposter syndrome 13:56 - "Why you?" Proving you're the right founder 16:38 - The Walt Disney story: surfacing hidden value 18:34 - You're too close to your own pitch deck 19:29 - LinkedIn and video: where investors hunt 21:54 - Headshots and the team slide that kills your raise 25:21 - Props that make founders memorable 28:16 - When to start, and your AI-era footprint (ChatGPT) 30:37 - Books, content, and the biggest bang for your buck 35:18 - Free quiz: rate your expert authority 36:44 - It's never too late

LINKS Blog post: https://ftb.bz/133B Watch on YouTube: https://ftb.bz/133V Podcast: https://ftb.bz/podcast Free Startup Fundraising Toolkit: https://ftb.bz/raise-yt

From Christine Blosdale: Free Expert Authority quiz: https://expertauthorityquiz.com Website: https://www.christineblosdale.com LinkedIn: https://www.linkedin.com/in/christine-blosdale-579697168 Instagram: https://www.instagram.com/christineblosdale/

ABOUT FEEL THE BOOT Feel the Boot helps early-stage founders raise money and build companies that last. Lance Cottrell is an angel investor, founder of Anonymizer, and president of North Bay Angels, teaching the fundraising process he wishes he'd had when he started. New videos on pitching, investors, and startup strategy every week.

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.

Links

Blog 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

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/130B

Watch on YouTube: https://ftb.bz/130VYT

Free Fundraising Toolkit: https://core.feeltheboot.com/raise?utm_source=podcast&utm_medium=audio&utm_campaign=organic_content&utm_content=ep130

Subscribe to BootPrints: https://ftb.bz/join-p

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 have

Why investors bet on leaders, not products — and what they're actually looking for

How to develop your leadership identity before you start raising

The difference between thought leadership and just reciting your feature list

Where to start if you have zero public presence and a fundraise on the horizon

The mistakes founders make when trying to project credibility they haven't built yet

A dead simple weekly exercise your whole founding team can start today

Shayna 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

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.

CHAPTERS

0:00 Intro

0:32 Dave's path from hockey enforcer to serial entrepreneur

1:36 Building Achievers.com and the $110M exit

3:08 Why non-traditional founders have an edge

3:52 The enforcer mentality and entrepreneurial grit

7:05 Building for the future: swappable AI engines

8:25 AI models are commodities, not loyalties

10:30 AI is table stakes now

10:43 The dumbbell theory: where to build in the age of AI

15:53 AI visibility: does ChatGPT, Claude, or Gemini know your startup exists?

19:47 What separates visible companies from invisible ones

21:00 How to use LLMTel to check your AI visibility

23:01 What early-stage founders should do now to show up in AI

25:18 GEO vs. SEO: what's different, what's the same

26:48 Mid-roll break

27:09 The 1,440-minute time management system

31:04 Color-coding your day in 10-minute blocks

32:23 Constraint-based prioritization: always work on the bottleneck

34:36 Embracing uncertainty and getting comfortable with failure

36:23 Building things nobody wants (and how to avoid it)

38:27 Why Dave went so granular on time tracking

40:51 Surviving a traumatic brain injury while running multiple companies

41:51 Notifications are other people's priorities

46:54 It's going to suck, and that's normal

47:59 When to pivot vs. when to double down

50:23 Going to zero twice: Great Recession and COVID

53:03 Business as an infinite game

55:01 Closing thoughts

🔗 LINKS & RESOURCES

Dave Burnett's AI Visibility Tool (LLMTel): https://llmtel.com

Dave's Digital Marketing Agency: https://aokmarketing.com

Dave's Book "From Bricks to Clicks": https://aokmarketing.com/book

Dave 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.

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/127B

Watch the video: https://ftb.bz/127V

[FREE TOOL] THE INVESTMENT READINESS SCORECARD

Don'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/raise

WHAT 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" Trap

1:30 Why 99% of Success is Decided Before the Pitch

3:15 Filter 1: The Harsh Math of Venture Capital

5:45 The "Corpse Audit": Why Timing is Your Delta

8:10 Case Study: The "Empty Box" Pitch at North Bay Angels

11:20 Filter 2: Proving Customer Hunger

14:45 Filter 3: Defensibility & The First-Mover Fallacy

17:30 Filter 4: The Machine & Unique Insights

20:15 Is Your Startup Default Alive or Default Dead?

22:00 Your Next Step: The Readiness Scorecard

ABOUT FEEL THE BOOT

I’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

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 STEPS

1. 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-outreach

2. 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/intensive

In 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

🛑 Stop Networking! Build Trust and Community to Fund Your Startup | David Homan

Are 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 & Links

Find the full transcript and blog post here:

👉 https://ftb.bz/125B

Watch the video:

🎥 https://ftb.bz/125V

Connect 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