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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Cardiologist Jim Min watched too many 50-year-olds die with no heart-attack warning. He co-founded Cleerly to automate detailed coronary scans—no invasive procedures, no endless manual work.

Yet healthcare’s glacial pace, payers, and federal approvals all stand in his way.

Hear how he’s testing AI across thousands of patients, fighting for universal insurance coverage, and coping with near-burnouts. If you’re a founder navigating hyper-regulated markets, Jim’s journey is the blueprint.

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Why You Should Listen

1. Heart Disease Kills More Than All Cancers Combined – The staggering truth behind silent heart attacks (and why most diagnoses come too late).

2. Jim’s Big Bet on Early Detection – He’s using advanced AI to spot “dangerous plaque” long before a patient gets chest pain or drops dead.

3. A 10–15 Year Fight to Save Lives – The brutal reality of building a medtech startup in a system that moves slower than any other.

4. Surviving a 17-Day Runway – How his mission-focus (and supportive backers) pulled Jim’s startup back from the brink.

5. Why repeated failure drives game-changing breakthroughs

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Keywords

Heart Disease Detection, Medtech Startup, Coronary CT Angiogram, AI in Healthcare, Early Heart Attack Prevention, FDA Approval Process, CPT Code Reimbursement, Plaque Imaging, Cardiovascular Innovation, Clinical Trials

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(00:00:00) Embracing Failure & Surviving Dark Days

(00:01:56) From Cardiologist to Startup Founder

(00:03:07) What Most People Don’t Know About Heart Attacks

(00:06:39) Using AI & Imaging to Predict Heart Attacks

(00:09:19) Why Cleerly Needed to Exist

(00:16:34) The Reality of Healthtech

(00:20:41) How Cleerly Built its First Product—and Why it Wasn’t an MVP

(00:28:33) Raising $225M to Prove a Radical Idea

(00:33:57) Finding Product-Market Fit & the Fight Worth Having

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Adam Robinson once struggled with a stagnant email SaaS stuck at $3M ARR, but he kept experimenting until he found how to solve a problem no one else was tackling—and everything changed. Suddenly, buyers were begging for his identity-based marketing tool—so he spun out Retention.com and grew it to $14M+ in annual profit with no outside funding.

In this episode, Adam reveals why he ignored “scalable hacks” until his product proved undeniable, the two keys that finally unleashed product-market fit, and how he uses no-friction brand marketing on LinkedIn to sign up thousands of new leads.

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Why You Should Listen

1. He chose profit over fundraising – Adam shows how ignoring “growth-hack hype” and focusing on real word-of-mouth built a wildly profitable SaaS.

2. Shocking pivot to product-market fit – A failed email tool spun out a game-changing identity product that users demanded.

3. The #1 trap killing early-stage founders – Why “growth hacking” tactics fail without genuine pull, and what to do instead.

4. Bootstrapping to $14M profit – His surprising path from 3M stalled ARR to unstoppable momentum (with a team of only six).

5. LinkedIn brand building done right – How to attract thousands of perfect-fit leads—no spammy sequences required.

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Keywords

Bootstrapped SaaS, Product Market Fit, Email Marketing Growth, Founder Lessons, B2B LinkedIn Strategy, High Profit Margins, Startup Pivot, Word-of-Mouth Marketing, Early-Stage Experimentation

Timestamps
(00:00:00) Intro
(00:01:57) A Bootstrap Story
(00:06:33) Why Bootstrapping Often Means You Can't Lose
(00:10:36) The downside of raising VC
(00:19:53) A Case Study: Constant Contact
(00:22:45) Find an Unsolved Porblem
(00:32:06) PMF and Word of Mouth
(00:46:45) Piece of Advice

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Dan Park joined Clutch when it was selling 20 cars a month. Then he grew it from $20M in 2019 to $200M in sales by 2022. He was one of Canada's fastest growing companies. Just as he was going to close a $100M round, the macro changed completely. Suddenly, he was left with only six weeks of cash. He was forced to go through a 97% down round at a $15M valuation.

Just two years later, he not only grew right back to a $575M valuation, he also doubled revenue from its previous peak to $400M.

This episode unpacks every near-disaster move, including turning off test-drives (and why it worked), re-engineering unit economics in real time, and renegotiating debt so Clutch could keep buying cars.

Dan’s hard-won lessons will change the way you think about speed, iteration, and survival.

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Why You Should Listen

1. He had just six weeks of runway – Find out exactly how Dan rescued Clutch from the brink.

2. Taking a car startup to $400M in sales – The surprising moves that made consumers buy cars online, sight unseen.

3. Cutting 75% of staff—then doubling revenue – The inside story of Clutch’s brutal pivot and swift rebound.

4. How to survive capital-intensive nightmares – Lessons on debt, term sheets, and crisis-mode fundraising.

5. Why fast iteration trumps everything – Dan’s secret to making big bets—then yanking them back if needed.

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Keywords

Used Car Marketplace, Capital-Intensive Startup, Near-Bankruptcy Turnaround, Automotive E-Commerce, Cash Flow Management, Startup Layoffs, Rapid Iteration, Debt Restructuring, Growth vs. Profitability, Founding Team Dynamics

Timestamp
(00:00:00) Intro
(00:02:23) The Birth of Clutch
(00:04:37) The Chicken and Egg Problem
(00:08:31) How Do We Scale This?
(00:14:21) Baby Steps and Achievable Milestones
(00:22:45) Becoming Profitable
(00:34:45) Do Whatever Makes Sense for The Business
(00:37:29) Finding Product Market Fit
(00:42:23) Piece of Advice

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Noah Greenberg grew a content-distribution product from zero to $1M ARR in just one year (and to $4M in 2 years) by focusing on a single channel most founders underrate: LinkedIn. He posted insights daily, highlighted key players in his industry, and made it impossible for prospects not to notice him.

In this episode, Noah reveals the exact step-by-step playbook, including how to structure 3-month pilots for fast feedback, craft DMs that actually get replies, and pick the right content “watering holes” so your future customers come to you eager to sign.

If you're a founder trying to figure out your go-to-market approach, you need to see what Noah did.

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Why You Should Listen

1. Turning LinkedIn into a Free PR Engine – Noah shows how daily micro-posts drive high-value leads without needing to go viral.

2. Finding Your First 10 Customers with 3-Month Pilots – Short trials = instant feedback on who’ll stay and who’ll churn.

3. Never Stop Triangulating – How 50 customer conversations per month reveal the right product, price, and packaging.

4. Selling without Selling – The “this isn’t a pitch” call that makes prospects lean in and ask, “Wait, how do we buy?”

5. Earning Credibility at Scale – Noah’s “watering hole” posts spark real engagement from decision-makers (and reel in 5-figure deals).

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Keywords

B2B Sales, LinkedIn Strategy, Early-Stage Growth, Founders’ Playbook, Bootstrapped Startup, Content Distribution, Sales Prospecting, Pilot Contracts, Outbound Leads, Product-Market Fit

Timestamps
(00:00:00) Intro
(00:02:35) Stacker's Origin Story
(00:06:00) How to generate warm leads
(00:15:53) How to use LinkedIn for lead gen
(00:21:42) No One Wants To Be Pitched
(00:26:06) How to get feedback on pricing
(00:38:08) LinkedIn Go-To-Market Strategy
(00:42:20) Breaking Above The Noise

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We break down the real startup playbook: fake users, fake traction, real secondaries. From starting a company with zero customers, to raising millions and launching a VC fund that's built to lose money, Jack shares the blueprint for getting rich (without working hard).

Forget chasing product-market fit.

Start chasing growth, money, and, most of all, hype.

Why You Should Listen

• Why you need to spend most of your time fundraising.
• Learn exactly how to fake traction, drive FOMO and raise millions-- even with a terrible product.
• Get Jack's ultimate playbook for quitting early and winning big (without working hard)
• How secondaries can make you rich BEFORE your startup fails.
• Why League of Legends is the key to startup success

Keywords

startup fundraising, pivot strategy, early stage VC, founder mistakes, product market fit, startup advice, venture capital, startup growth, entrepreneur mindset, founder stories

(00:00:00) Intro: Why Quitters Win and Fundraising Beats Traction

(00:02:54) Ex-Googlers Can’t Hack It as Founders

(00:03:12) Raising Money is Your Only Job

(00:10:49) How to Fake User Growth & Create FOMO

(00:14:18) Quit Fast, Pivot Faster

(00:15:28) Jabroni Capital: The World’s Worst VC Fund

(00:26:26) Hiring Hacks: How to Convince People to Join Your Startup

(00:28:27) Adam Neumann: Hero or Villain?

(00:38:16) The Real Jack Kuveke: Satire, Startups, and Why VC is Broken

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