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Feel the Boot

Feel the Boot

By: Feel the Boot
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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.

Copyright 2019-2023 Feel the Boot
Career Success Economics Leadership Management Management & Leadership
Episodes
  • The Real Odds of Getting Funded, Stage by Stage
    Sep 30 2026

    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

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    10 mins
  • Why Great Advisors Give Terrible Startup Advice
    Aug 25 2026

    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.

    Toolkit uses the generic ftb.bz/raise. Podcast volume doesn't justify a dedicated short link.

    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.

    Some directories cap descriptions around 4,000 characters and strip formatting. This is well under, and it degrades fine to plain text.

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    19 mins
  • Investors Judge You Before You Say a Word
    Jun 23 2026

    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.

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    37 mins
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