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How I Bought an $8M/Year Company With Only $5,000
Ever wonder how someone bought an $8M/year company with only $5,000? Gary Shelton did just that, and in this interview, he reveals his exact model. Gary is "The Coaching King," having acquired, scaled, and sold 12 different businesses over the last 50 years, each hitting 8-figures per year. He explains why mindset is the #1 reason most entrepreneurs never hit $1M a year in revenue and shares the lessons he learned from his mentor who built the first black-owned billion-dollar company. If you want to learn how to acquire businesses with little of your own money, build systems that allow them to run without you, and develop the perseverance to succeed, this conversation is for you. Check out the company: https://goshelton.com
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š NETWORK BEFORE YOU NEED IT (6 LESSONS THAT MADE SEAN $15M)
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ā¶ Get my eBook free - https://welivetobuild.com/network
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š WORK WITH ME
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ā¶ Buy 300 Lessons From 300 Founders: https://welivetobuild.com/300-lessons-ebook
ā¶ Book a Paid Advisory Session: https://welivetobuild.com/book-a-call
ā¶ Startup Fundraising: https://welivetobuild.com/fundraising
ā¶ Sponsor the Channel: https://www.welivetobuild.com/sponsorship
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š CONNECT WITH SEAN
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ā¶ LinkedIn: https://linkedin.com/in/seanweisbrot
ā¶ Inquiries: welivetobuild@gmail.com
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š CHAPTERS
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00:00 - "Life is Quick, Man."
01:34 - The REAL Reason Businesses Fail to Hit $1M/Year
03:42 - The Money Lesson My Grandfather Taught Me at Age 4
06:35 - My First Million-Dollar Business Acquisition
08:29 - The #1 Thing That Gives a Business REAL Value
11:19 - How I Bought an $8M/Year Company With $5,000
14:48 - "I'm Not Betting The Farm Unless The Crops Are On Fire"
17:22 - The 2 Things to Look For When Buying a Business
22:20 - The Hardest Part of Being an Entrepreneur
30:45 - "I Don't Work. I Do What I Love."
Leave a Review (it truly helps us grow): https://welivetobuild.com/reviewHow I Made $15M: https://welivetobuild.com/networkSubscribe on YouTube: https://youtube.com/@seanweisbrotFollow Sean on LinkedIn: https://linkedin.com/in/seanweisbrotMore episodes
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302. Stop Wasting Money on Big AI Models (Do This Instead)
27:46||Ep. 302Are your AI inference costs starting to eat into your startup's budget? In this episode, I sit down with Rob May to discuss the impending shift in the AI industry: moving from massive, expensive frontier models to optimized, task-specific workflows. Rob explains why using a massive model for a simple task is like paying an astrophysicist to balance your checkbook, and how routing requests to smaller models can significantly cut down on your token spend. We also dive into the realities of startup hiring, including why executives must network for talent months in advance and how "experienced" corporate hires can completely derail your early-stage systems. Finally, Rob shares his ultimate advice for founders: why cozying up to massive markets is the best way to de-risk your business. Check out the company: https://neuromatic.com----------------------------------------------------------------------------------------------------------------------------š NETWORK BEFORE YOU NEED IT (6 LESSONS THAT MADE SEAN $15M)----------------------------------------------------------------------------------------------------------------------------Get my brand new eBook free - https://welivetobuild.com/network-----------------------------------š WORK WITH ME-----------------------------------ā¶ Buy 300 Lessons From 300 Founders: https://welivetobuild.com/300-lessons-ebookā¶ Book a Paid Advisory Session: https://welivetobuild.com/book-a-callā¶ Startup Fundraising: https://welivetobuild.com/fundraisingā¶ Sponsor the Channel: https://www.welivetobuild.com/sponsorship---------------------------------------------š CONNECT WITH SEAN---------------------------------------------ā¶ LinkedIn: https://linkedin.com/in/seanweisbrotā¶ Inquiries: welivetobuild@gmail.com---------------------------š CHAPTERS---------------------------00:00 - Why Founders Must Network Before Hiring03:45 - The $30,000 Corporate Hiring Mistake06:20 - Selling to IT Professionals vs. Sales Teams08:15 - The Alex Hormozi Free Content Strategy10:50 - How to Reduce High AI Inference Costs13:30 - Tasks vs. Models: The Future of AI16:45 - Moving AI Workflows to Microservices21:10 - The "Big Market" Secret to Entrepreneurship
301. The Secret ADHD Advantage Nobody Talks About
31:35||Ep. 301Does having ADHD make you a better entrepreneur? Transformation artist and former actress Helen Millar believes her neurodivergence is actually her greatest superpower. In this episode, Helen reveals why the ADHD brain's high risk tolerance and elite pattern recognition give founders a massive edge in business. We explore how to trust your deepest intuition, why playing small is the most dangerous thing you can do, and why having the wrong support system is worse than having none at all. Helen also shares her wildly unorthodox approach to networking , and why she walked away from a successful acting career to maintain her integrity. Plus, we finally uncover the psychological truth behind "Resting Bitch Face" and why itās actually a sign of intense, ADHD-driven deep listening. Check out the company: https://hearthealer.co.uk----------------------------------------------------------------------------------------------------------------------------š NETWORK BEFORE YOU NEED IT (6 LESSONS THAT MADE SEAN $15M)----------------------------------------------------------------------------------------------------------------------------Get my brand new eBook free - https://welivetobuild.com/network-----------------------------------š WORK WITH ME-----------------------------------ā¶ Buy 300 Lessons From 300 Founders: https://welivetobuild.com/300-lessons-ebookā¶ Book a Paid Advisory Session: https://welivetobuild.com/book-a-callā¶ Startup Fundraising: https://welivetobuild.com/fundraisingā¶ Sponsor the Channel: https://www.welivetobuild.com/sponsorship---------------------------------------------š CONNECT WITH SEAN---------------------------------------------ā¶ LinkedIn: https://linkedin.com/in/seanweisbrotā¶ Inquiries: welivetobuild@gmail.com---------------------------š CHAPTERS---------------------------00:00 - The Secret ADHD Advantage 01:47 - Trusting Your Intuition & Playing Big 03:40 - Spotting Fake Support Systems 06:14 - The "Piss Up in a Brewery" Networking Guide 08:40 - How to Get Noticed When You're a "Nobody" 10:38 - The Art of Being Interested (Not Just Interesting) 14:06 - Don't Be a Slave to Your Business 16:56 - Why I Walked Away From Acting 18:12 - The Dark Side of Media Manipulation 21:50 - How to Become a Transformation Artist 26:54 - The Truth About "Resting Bitch Face" and ADHD 30:00 - Becoming a Master of Meaning
300. How One Free Mentor Made Me $15,000,000
55:36||Ep. 300For our 300th episode, the podcast is officially rebranding to focus on business networking! To celebrate, I brought on my very first mentor, Meir Simhi. Years ago in China, Meir helped me realize my true value in networking, which eventually led to me generating $15 million in crypto fundraising sales.In this episode, Meir breaks down his new "Product Theory" and why asking "what to sell" is the wrong question. We deconstruct my new business idea (feeding your frustrations to your dog) and explore the true definition of a market. Check out the company: https://brandmasters.io----------------------------------------------------------------------------------------------------------------------------š NETWORK BEFORE YOU NEED IT (6 LESSONS THAT MADE SEAN $15M)----------------------------------------------------------------------------------------------------------------------------ā¶ Get my eBook free - https://welivetobuild.com/network-----------------------------------š WORK WITH ME-----------------------------------ā¶ Buy 300 Lessons From 300 Founders: https://welivetobuild.com/300-lessons-ebookā¶ Book a Paid Advisory Session: https://welivetobuild.com/book-a-callā¶ Startup Fundraising: https://welivetobuild.com/fundraisingā¶ Sponsor the Channel: https://www.welivetobuild.com/sponsorship---------------------------------------------š CONNECT WITH SEAN---------------------------------------------ā¶ LinkedIn: https://linkedin.com/in/seanweisbrotā¶ Inquiries: welivetobuild@gmail.com---------------------------š CHAPTERS---------------------------00:00 - Episode 300 & The Business Networking Rebrand02:37 - The Loneliest Part of Entrepreneurship05:08 - Why Chasing Respect Repels People09:02 - How Meir Mentored Sean in China15:47 - The WeChat Course Failure19:10 - How Networking Made Sean $15 Million in Crypto23:51 - Why E-Commerce is Just "Commerce" Now26:24 - "The Product Theory": How to Decide What to Sell36:21 - Deconstructing Sean's "Dog Treat" Business Idea46:55 - The 4 Axes of Defining a Market54:26 - Why Shenzhen, China is the Future
299. Why "Self-Improvement" is Ruining You (And What to Do Instead)
27:14||Ep. 299Are you obsessed with self-improvement? Mental performance coach and former Wall Street hedge fund manager Evan Marks argues that constantly trying to "fix" yourself actually takes you further away from who you really are. In this episode, Evan explains why he completely rejects "positive psychology" in favor of "opportunistic reality". He trains high-achievers to treat their negative emotions as data and be ready for chaos like a "jaguar in the brush". Check out the company: https://m1performancegroup.com----------------------------------------------------------------------------------------------------------------------------š NETWORK BEFORE YOU NEED IT (6 LESSONS THAT MADE SEAN $15M)----------------------------------------------------------------------------------------------------------------------------ā¶ Get my eBook free - https://welivetobuild.com/network-----------------------------------š WORK WITH ME-----------------------------------ā¶ Buy 300 Lessons From 300 Founders: https://welivetobuild.com/300-lessons-ebookā¶ Book a Paid Advisory Session: https://welivetobuild.com/book-a-callā¶ Startup Fundraising: https://welivetobuild.com/fundraisingā¶ Sponsor the Channel: https://www.welivetobuild.com/sponsorship---------------------------------------------š CONNECT WITH SEAN---------------------------------------------ā¶ LinkedIn: https://linkedin.com/in/seanweisbrotā¶ Inquiries: welivetobuild@gmail.com---------------------------š CHAPTERS---------------------------00:00 - The Fear of Regret00:26 - The Hardest Part of Being an Entrepreneur01:21 - Reinventing Yourself at 4603:06 - The Fear of Failure vs. Regret04:39 - Wall Street Stress & Uncertainty05:46 - Why Positive Psychology is Fluff10:50 - Why Self-Improvement is Ruining You12:10 - How to Build Trust and Be Vulnerable13:35 - Gen Z, Masculinity, & Coaching the Elite15:20 - Does Trauma Create High Achievers?20:18 - The Pain of Denial & Ignorance22:30 - The "Leaf vs. Root" Metaphor23:51 - Losing Purpose After a Big Exit
298. Why VCs Really Reject Your Startup (The "No Conviction" Truth)
36:36||Ep. 298What does it actually mean when a venture capitalist says they "don't have conviction" in your startup? Vaughn Crowe, an investor at MVP Capital , explains why VCs struggle to give founders honest feedback and what that dreaded rejection phrase really translates to. In this interview, Vaughn reveals how he sniffs out scammers versus real entrepreneurs by evaluating their true desire to build a big business. We discuss why having a massive advisory board at the pre-seed stage can be a major red flag , and whether founders should take a salary from their funding or bootstrap completely. Plus, he explains why leading your first VC meeting with a pitch deck is a fatal flaw and what you should do instead. Check out the company: https://nvpcapital.com----------------------------------------------------------------------------------------------------------------------------š NETWORK BEFORE YOU NEED IT (6 LESSONS THAT MADE SEAN $15M)----------------------------------------------------------------------------------------------------------------------------ā¶ Get my eBook free - https://welivetobuild.com/network-----------------------------------š WORK WITH ME-----------------------------------ā¶ Buy 300 Lessons From 300 Founders: https://welivetobuild.com/300-lessons-ebookā¶ Book a Paid Advisory Session: https://welivetobuild.com/book-a-callā¶ Startup Fundraising: https://welivetobuild.com/fundraisingā¶ Sponsor the Channel: https://www.welivetobuild.com/sponsorship---------------------------------------------š CONNECT WITH SEAN---------------------------------------------ā¶ LinkedIn: https://linkedin.com/in/seanweisbrotā¶ Inquiries: welivetobuild@gmail.com---------------------------š CHAPTERS---------------------------00:00 - How VCs Spot Fake Founders & Scammers03:37 - Should You Hide Competing Term Sheets from VCs?09:30 - Why Advisory Boards are a Red Flag for Early Startups17:54 - Should Founders Take a Salary?21:50 - Do Founders Still Need VCs in the Age of AI?24:26 - Why VCs Won't Give You Honest Feedback30:00 - The Real Meaning of "I Don't Have Conviction"34:30 - Never Open a VC Meeting With a Pitch Deck
297. Why Your Social Media Content Isn't Getting Subscribers
49:14||Ep. 297Are you getting thousands of views on your YouTube Shorts but struggling to turn them into loyal subscribers or paying clients? Ben Pines, who helped scale Elementor from $0 to $100M ARR, explains exactly why your social media strategy is falling flat and how to fix it. In this live "workshop" style episode, Ben and Sean deconstruct Seanās own content strategy. They discuss why AI has completely killed generic SEO content, why short-form video often leads to "empty views," and the secret to transitioning from a generic content creator to a highly paid trusted advisor. Ben reveals how to use the "Ezra Klein Method" to turn your content into a deep, problem-solving engine that naturally attracts your ideal audience. Check out the company: https://benpines.com----------------------------------------------------------------------------------------------------------------------------š NETWORK BEFORE YOU NEED IT (6 LESSONS THAT MADE SEAN $15M)----------------------------------------------------------------------------------------------------------------------------ā¶ Get my eBook free - https://welivetobuild.com/network-----------------------------------š WORK WITH ME-----------------------------------ā¶ Buy 300 Lessons From 300 Founders: https://welivetobuild.com/300-lessons-ebookā¶ Book a Paid Advisory Session: https://welivetobuild.com/book-a-callā¶ Startup Fundraising: https://welivetobuild.com/fundraisingā¶ Sponsor the Channel: https://www.welivetobuild.com/sponsorship---------------------------------------------š CONNECT WITH SEAN---------------------------------------------ā¶ LinkedIn: https://linkedin.com/in/seanweisbrotā¶ Inquiries: welivetobuild@gmail.com---------------------------š CHAPTERS---------------------------00:00 - Why You're Getting Views but No Subscribers01:45 - Deconstructing a Failing Content Strategy03:40 - The Golden Rule of Content: What Pays the Rent?08:35 - Why "Curiosity" is Killing Your Podcast12:40 - How to Tie Your Content Directly to Your Business18:00 - Why AI Has Ruined Generic SEO Content19:25 - The "Ezra Klein" Method for Building True Authority22:50 - Stop Pretending You Know Everything26:30 - Flip the Script: Solve Client Problems Live38:30 - The Truth About YouTube Shorts & Distribution43:30 - Elementorās $100M Lesson: You Need a Bigger Story
296. The 150-Year Vision for Humanity
28:54||Ep. 296What will human civilization look like in 150 years? Abdo John Hajj, partner at Type One Ventures, believes we are at the beginning of a deep tech supercycle that will transition humanity into a "Type 1 Civilization"āone that harnesses the full energy of its host star and becomes truly interplanetary. In this interview, Abdo explains why space is not just about rockets, but about building the infrastructure for abundance. We discuss why Tesla's Optimus robots will likely colonize Mars before humans do , the critical need for a "circular economy" in space (mining water for fuel) , and the geopolitical reality of who will enforce the law on the lunar surface. Check out the company: https://type1ventures.com----------------------------------------------------------------------------------------------------------------------------š NETWORK BEFORE YOU NEED IT (6 LESSONS THAT MADE SEAN $15M)----------------------------------------------------------------------------------------------------------------------------ā¶ Get my eBook free - https://welivetobuild.com/network-----------------------------------š WORK WITH ME-----------------------------------ā¶ Buy 300 Lessons From 300 Founders: https://welivetobuild.com/300-lessons-ebookā¶ Book a Paid Advisory Session: https://welivetobuild.com/book-a-callā¶ Startup Fundraising: https://welivetobuild.com/fundraisingā¶ Sponsor the Channel: https://www.welivetobuild.com/sponsorship---------------------------------------------š CONNECT WITH SEAN---------------------------------------------ā¶ LinkedIn: https://linkedin.com/in/seanweisbrotā¶ Inquiries: welivetobuild@gmail.com---------------------------š CHAPTERS---------------------------00:00 - Why Space is the Next Deep Tech Supercycle02:20 - The "Space HoldCo" Strategy: Investing in Infrastructure06:30 - Elon Musk: The Ultimate "Venture Operator"08:35 - The Reality: Why Space Startups Need Government Contracts12:35 - Star Trek vs. Star Wars: The Future of Civilization14:15 - Geopolitics: Who Enforces Law on the Moon?16:45 - Sending Tesla Bots to Build Martian Colonies21:00 - The Next-Gen Space Station: Axiom Space22:20 - Mining the Moon for Water & Fuel27:00 - The Power of Vision & Systems Thinking
295. Stop Hiring Advisors Who Want a Retainer (The Equity Playbook)
30:09||Ep. 295Why do most startups waste thousands of dollars on advisors who deliver zero results? Ron Levin, a partner at Alumni Ventures, explains why you should never pay a retainer to an advisor and how to structure equity-based deals that actually align incentives. In this interview, Ron shares his transition from co-founding TravelPerk (a unicorn startup) to becoming a venture capitalist. He reveals why he prefers investing over operating, the "Cold Outreach" myth that stops founders from reaching VCs, and the new trend of startups hitting $1M ARR before even raising a seed round. He also breaks down his "Super Angel" scout program and why the best founders are often the ones who failed their first time. Check out the company: https://alumniventures.com----------------------------------------------------------------------------------------------------------------------------š NETWORK BEFORE YOU NEED IT (6 LESSONS THAT MADE SEAN $15M)----------------------------------------------------------------------------------------------------------------------------ā¶ Get my eBook free - https://welivetobuild.com/network-----------------------------------š WORK WITH ME-----------------------------------ā¶ Buy 300 Lessons From 300 Founders: https://welivetobuild.com/300-lessons-ebookā¶ Book a Paid Advisory Session: https://welivetobuild.com/book-a-callā¶ Startup Fundraising: https://welivetobuild.com/fundraisingā¶ Sponsor the Channel: https://www.welivetobuild.com/sponsorship---------------------------------------------š CONNECT WITH SEAN---------------------------------------------ā¶ LinkedIn: https://linkedin.com/in/seanweisbrotā¶ Inquiries: welivetobuild@gmail.com---------------------------š CHAPTERS---------------------------00:00 - Founder vs. Investor: Which is Better?02:20 - How to Find the "One in a Million" Startup05:08 - Why Venture Capital Still Works (Despite the Failures)07:54 - The "First Check" Myth: Who Really Invests First?08:35 - Why VCs Brag About Seeing thousands of Decks10:04 - The "Cold Outreach" Truth: How to Get a Meeting14:40 - Stop Hiring Advisors on Retainer (Do This Instead)17:00 - How to Use Advisors to Open Doors (The TravelPerk Story)19:50 - My Worst Investment Mistake ($50k to Zero)21:28 - The New Standard: $1M ARR for Seed Rounds?25:40 - Alumni Ventures Investment Strategy (Co-Investing)27:28 - The #1 Career Lesson: Do What You Actually Like
294. Stop Buying Stocks on Fidelity (Do This Instead)
27:52||Ep. 294Is AI about to replace your stock broker? Christine Healey, a pre-IPO investment expert, explains why Claude AI missed a critical detail in a deal that could have cost her client millionsāand why human brokers are still essential in the private market. In this interview, Christine and Sean discuss the "wild west" of pre-IPO investing, how to avoid scams when buying shares of companies like SpaceX and Stripe, and the secret tax strategies (like the Peter Thiel Roth IRA hack) that can save you millions. They also debate whether employees selling shares before an IPO is a red flag or just smart financial planning. Check out the company: https://healeypreipo.com----------------------------------------------------------------------------------------------------------------------------š NETWORK BEFORE YOU NEED IT (6 LESSONS THAT MADE SEAN $15M)----------------------------------------------------------------------------------------------------------------------------ā¶ Get my eBook free - https://welivetobuild.com/network-----------------------------------š WORK WITH ME-----------------------------------ā¶ Buy 300 Lessons From 300 Founders: https://welivetobuild.com/300-lessons-ebookā¶ Book a Paid Advisory Session: https://welivetobuild.com/book-a-callā¶ Startup Fundraising: https://welivetobuild.com/fundraisingā¶ Sponsor the Channel: https://www.welivetobuild.com/sponsorship---------------------------------------------š CONNECT WITH SEAN---------------------------------------------ā¶ LinkedIn: https://linkedin.com/in/seanweisbrotā¶ Inquiries: welivetobuild@gmail.com---------------------------š CHAPTERS---------------------------00:00 - Why AI Can't Replace Investment Brokers (Yet)01:30 - The Human Touch in Private Equity Deals02:20 - Direct Shares vs. SPVs: Which is Better?04:40 - Pre-IPO Scams: How to Not Get Ripped Off08:15 - Why Employees Sell Shares Before an IPO10:45 - How to Invest in SpaceX & OpenAI13:20 - What Does "Pre-IPO" Actually Mean?16:00 - Early Stage vs. Late Stage Venture Risk18:00 - Taking Fees as Equity (The "Carry" Strategy)19:25 - The Taboo of Secondary Sales21:00 - The "WeWork" Lesson: Why Cash Flow Matters24:00 - The Peter Thiel Tax Hack (Roth IRA Investing)26:50 - The #1 Lesson: Details Make the Deal