Wesley turned a simple AI headshot generator into a $10M ARR, profitable company—in just two years.

He was fired from his job, broke in San Francisco, and, after getting rejected by 30 VCs, down to his last few thousand bucks. But Wesley saw a moment: generative AI was taking off, and no one was tackling AI headshots.

Fast-forward two years, and he’s doing $10M in revenue, profitable, with just 10 employees. He shares every bold tactic—bundling random AI packs, hacking Google rankings, landing affiliates, and manually doing customer support until there was no time left. Wes shares insights that every founder should know, including how he navigated intense competition, handled burnout, and maintained growth without a sales team. You’ll walk away with clear, actionable strategies you can apply immediately.

If you want a raw, practical take on zero-to-10M product-market fit in the AI era, this one’s unmissable.

Why You Should Listen:

• How Wes grew Aragon to $10M ARR—without burning any money.

• The guerrilla marketing tactics Wes used to turn a $30 idea into millions of revenue.

• Why starting early let him outrun lookalike competitors.

• How one affiliate blog post drove more than 50% of early sales.

• How he managed high early churn in the early days until the product improved.

Keywords:

AI startups, early-stage growth, product-market fit, AI headshots, founder stories, affiliate marketing, startup tactics, SEO for startups, guerrilla marketing, startup growth strategies

(00:01:54) Zero to $10M in Two Years

(00:02:34) Exploring Ideas Before AI

(00:05:25) Discovering the AI Headshot Opportunity

(00:07:37) How Getting Fired Led to a Startup

(00:18:31) Doubling Down on Professional Headshots

(00:24:11) Early Guerrilla Marketing and Traction

(00:27:59) From $2K to $200K a Month

(00:32:13) Affiliate Marketing as a Growth Lever

(00:43:18) The Moment of True Product Market Fit

(00:47:18) Surviving Near-Failure and Burnout

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Mike first raised $30M for a marketplace that never truly had product-market fit. Then he bet only $10K on ButcherBox. A few years later, he's doing $550M in revenue and he's profitable.

The difference is in his first startup he was just catering to investors— in his second one only to customers. If you’re an early founder chasing growth, listen to how Mike ditched vanity metrics, found sustainable traction, and grew ButcherBox past $500M in revenue—with no outside funding.

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Why You Should Listen

1. Why not raising can often be a powerful forcing function.

2. Why what VCs want is often not the same as what customers want.

3. How to differentiate in what seems like a commoditized market.

4. Why there is no stronger force in startups than true product-market fit.

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Keywords

product market fit, bootstrapping, butcherbox, direct to consumer, CPG subscription, grass fed beef, founder lessons, Kickstarter, food startup, early stage founder

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(00:00:00) Mastering the VC Game

(00:01:45) How I Raised $30M Without Product Market Fit

(00:08:21) Why my VC-backed Startup Failed

(00:15:34) Growing Revenue but Losing Money

(00:28:07) Early Signals of Real Product Market Fit

(00:34:59) Solving Supply Chain to Scale ButcherBox

(00:39:43) Bootstrapping to $550M (The Power of Constraints)

(00:51:18) Product Market Fit from Day One

(00:52:42) Why Founders Need a Lifestyle Plan

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Gopi Rangan has invested in 29 early-stage startups from scratch. He shares a simple but powerful approach to picking the right VCs, structuring your pitch (long-term vision + short-term plan + fuzzy mid-term path), and proving you are the sort of founder every pre-seed investor craves.

If you’re raising a pre-seed or seed, Gopi’s tips will make your process faster, more targeted, and a lot less painful.

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Why You Should Listen

1. The 2-minute test for "real" pre-seed investors – Spot VCs who truly lead early rounds vs. those who waste your time.

2. His 3-step framework for finding your perfect lead – Forget the 100 investor pipeline. Zero in on 10 prospects who’ll actually write a check.

3. How to balance short-term execution with a massive mission – Win over pre-seed VCs by knowing your next 6 months and your 10-year ambition.

4. Why "business acumen" beats everything – Gopi explains how it trumps domain expertise or brand-name credentials.

5. When to be fuzzy, when to be precise – The counterintuitive approach that shows you’re open to customer feedback while still having big vision.

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Keywords

Pre-seed Funding, Early-Stage VC, Business Acumen, Go-to-Market Strategy, Founder–Investor Fit, Strategic Networking, Seed Round Pitch, Warm Introductions, Mission-Driven Startups, Conviction Investing

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(00:00:00) Why Ruthless Prioritization Wins

(00:03:29) Why Investing at Pre-seed is Personal

(00:08:36) Investing When There Are Still Typos in the Pitch Deck

(00:12:23) Spotting Founders with Exceptional Business Acumen

(00:17:21) Great Ideas in the Hands of the Right Founder

(00:26:29) The Practical Guide to Raising Your Seed Round

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