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My First Million
18 case studies found
Gelt (Keith Wasserman) / Sky (Galena Wasserman)
by Keith Wasserman and Galena WassermanKeith Wasserman and his cousin Damian started Gelt in December 2008 by purchasing a single fourplex in Bakersfield for $150,000 with just 2.5% down ($5,000 borrowed, $10,000 credit card cash advance) during the financial crisis. Over the next decade, they grew to manage over $1 billion in real estate assets by focusing on value-add multifamily properties through strategic renovations and raising capital from 700+ accredited investors. Galena Wasserman runs Sky, a parallel real estate development company that acquires and renovates buildings through ground-up construction and adaptive reuse, with both operating on the principle of 'making money on the buy' by identifying undervalued properties and creating value before exit or hold.
Mike Brown's Oil & Gas Aggregation Company
by Mike BrownMike Brown founded an oil and gas mineral rights aggregation company in May 2013 with his former naval flight officer friend. Operating in the Midland Basin/Permian Basin, they bought fragmented mineral rights from private owners and packaged them for sale to private equity funds. With only 5 employees at peak and completely bootstrapped using other people's money to fund acquisitions, the company grew to handle 45-50 deals annually and eventually achieved an eight-figure exit.
Tiny Capital
by Andrew WilkinsonTiny Capital is a long-term holding company for profitable internet businesses founded by Andrew Wilkinson. The company acquires majority stakes in established, cash-flowing internet businesses across multiple verticals including design firms, SaaS products, job boards, and content platforms. Operating with a hands-off approach and conservative financing, Tiny Capital has grown to manage approximately 20 companies with 350-400 employees generating double-digit millions in revenue.
David's Tea
by David SegalDavid's Tea was founded in 2007 by David Segal and his distant cousin to make tea fun and accessible to mainstream North American consumers. The company grew to a $200 million revenue business with a $1 billion market cap at its peak before going public on the Nasdaq. Segal sold his stake in 2016 after internal management conflicts made the company lose focus on its core business.
f.ink
by Furconf.ink is an emerging tech incubator founded by Furcon (former CTO of AppLovin, which IPO'd at ~$20B valuation) that invests in young engineers building on cutting-edge technologies. Rather than a traditional startup with revenue metrics, f.ink operates as an investment/mentorship vehicle where Furcon provides capital, technical expertise, and intensive hands-on collaboration through a Discord community of founders exploring hardware+ML, crypto/DeFi, and other frontier technologies.
Ben & Jerry's
by Ben Cohen, Jerry GreenfieldBen & Jerry's was founded in 1978 by two former friends who met in PE class as poor runners and reunited when one was rejected from medical school. Starting with a $5 ice cream making course and $12,000 in seed funding, they initially struggled in their Vermont shop during winter but pivoted to selling pints directly to restaurants and convenience stores. When Pillsbury strong-armed distributors to drop Ben & Jerry's in favor of their Haagen-Dazs brand, the founders turned adversity into their greatest marketing opportunity, launching the viral 'What's the Dough Boy Afraid Of?' campaign that generated massive PR, consumer awareness, and growth.
Girdley Enterprises
by Michael GirdleyMichael Girdley runs Girdley Enterprises, a diverse holdco with over $100M in revenue across 8-10 businesses including Alamo Fireworks (20-30M+ revenue), Dura Software (a rollup generating multiple millions), a coding bootcamp (low eight figures in revenue), a drive-through coffee chain, and hirewithnear.com. His philosophy emphasizes finding good operators to run businesses while he focuses on strategy, partnerships, and capital allocation rather than day-to-day operations.
Missouri Star Quilting Company
by Al DoadMissouri Star Quilting Company is a bootstrapped, family-owned e-commerce business co-founded by Al Doad and his mom Jenny that generates nine figures in annual revenue. The company started when Al's mom discovered a six-month waitlist for machine quilting services, leading Al to buy a machine and launch a service business. Growth accelerated dramatically when they launched a YouTube channel featuring Jenny teaching quilting (now nearly 1M subscribers) and implemented a daily deal strategy inspired by Woot.com, combined with turning their manufacturing facilities into a tourist destination called the "Disneyland for quilters" that attracts 100,000+ visitors annually.
Carter Ventures (Independent Sponsor)
by Maitab (full name not provided in text)Maitab is a 29-year-old independent sponsor who acquires distressed D2C e-commerce brands and turnarounds them using operational excellence and rapid cash recovery strategies. Starting from a health issue at 17, he built several seven-figure e-commerce businesses in guitars and pedals before pivoting to private equity-style investing. His current portfolio includes three majority-owned platform companies (SoloWood Flowers, a succulent company, and an apparel brand) worth mid-eight figures in revenue, plus minority stakes in 8-10 other companies.
Zuru
by Nick MowbrayZuru is a toy manufacturing and consumer goods company founded by Nick Mowbray and his brother Matt, growing from a bootstrapped operation sleeping in bushes in China to a $2B+ revenue private company. The founders used relentless cold outreach, persistence through repeated rejection, and a focus on manufacturing excellence and automation to disrupt the toy industry and expand into FMCG categories. Today Zuru runs at ~40% net profit margins and operates globally with sophisticated automated production lines.
Formidable Fellowship
by AnandFormidable Fellowship is a nonprofit founded by Anand (and friend Raj) that provides $1,000 grants to middle and high school entrepreneurs who have proven revenue. Launched with $500K in funding, they received a few hundred applications in their first round, accepted 23 grantees, and have attracted contributions from notable entrepreneurs like Mesh from HubSpot and Sean Griffey from IndustryDive. The program serves as an MVP for Anand's larger vision of building a national network of schools of entrepreneurship.
Moonbug Entertainment
by ReneeMoonbug Entertainment, founded by Renee (formerly of Maker Studios and Disney), acquired undermonetized children's YouTube channels including Cocomelon, Blippi, and Little Baby Bum. The company scaled from ~$20M ARR in 2019 to $230M+ with $100M EBITDA in 4 years, then exited to Blackstone-backed Candle for $3 billion in 2023, demonstrating the massive value in aggregating and monetizing organic YouTube IP.
Touchland
Touchland transformed hand sanitizer from a commodity product into a luxury item by applying premium design, fragrance, and limited collaborations (Hello Kitty, Disney). The founder raised $67,000 on Kickstarter, achieved $1M in first-year revenue, and experienced explosive growth during COVID-19. Recently acquired for $880M with projected $130M annual revenue.
Multiple businesses (Chris Amon's portfolio)
by Chris AmonChris Amon is a serial entrepreneur running 6+ profitable side hustles simultaneously, generating approximately $8,000 per day in cash flow. His portfolio includes the Beaver Snacks e-commerce business (reselling Bucky's merchandise), pet cremation logistics, Bitcoin mining hosting on Facebook Marketplace, and concept-stage ideas like floating golf hole-in-one challenges and repurposing tourist trap businesses. He operates with a bias toward rapid validation, focusing on low-competition market segments with high-ticket pricing and strong margins.
Tommy Distressed Investing (Personal Business)
by TommyTommy is a solo distressed investing operator who specializes in buying bankruptcy claims—particularly in cryptocurrency—at steep discounts and waiting for payouts. Starting with a small hedge fund buying Mt. Gox claims in 2014 for ~$80 per Bitcoin and eventually realizing 40x+ returns, he's built a lifestyle business operating from low-cost jurisdictions, partnering with institutional firms on larger deals while personally compounding capital at 30-50% annually through claims work and selective deep-value positions.
Tiny (formerly Tiny Capital)
by Andrew WilkinsonTiny is Andrew Wilkinson's investment holding company that acquires and operates profitable businesses. Starting with $4-5 million in seed capital from his design agency MetaLab's profits in 2013, the company has grown to manage over $300 million in revenue across 30 businesses, with $65 million in ARR and $40+ million in EBITDA. The company went public via reverse merger in 2021 and now manages a $200 million fund alongside its core operations.
Eggcartons.com
by Sarah MooreSarah Moore acquired an existing multi-million dollar egg carton business (Eggcartons.com) with zero dollars and no prior experience in the industry. She grew the business post-acquisition through unconventional strategies including database scraping, mass outreach, finding free labor, and radical simplicity over innovation. Her story demonstrates how acquisition, aggressive outreach, and operational efficiency can scale an existing business without traditional funding.
Epic Gardening
by Kevin EspirituKevin Espiritu built Epic Gardening from a $300/month gardening blog into a $45M business through content marketing, product development, and strategic acquisitions. He grew primarily through YouTube and blogging, expanding into seed trays, plant varieties, and competing gardening properties. His journey exemplifies how passion projects can scale to nine-figure valuations through smart M&A and brand building.