099: Raising Capital, Deal Structure, and Scaling Multi-Million Dollar Companies with Dan Fleyshman


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Dan Fleyshman is a serial entrepreneur and the youngest founder of a publicly traded company in history.

At 23, after selling $15M worth of clothing in six department store chains and getting a $9.5M licensing deal with STARTER apparel, he went on to scale his “Who’s Your Daddy” energy drink into 55,000 retail stores.

He later launched Victory Poker, which scaled to $65M within 10 months and became a top 5 international poker brand. Unfortunately, poker was banned in the US during that time, and overnight the business imploded. Dan lost everything and was forced to start over from scratch.

While it was a tough blow, he describes it as the best thing that ever happened to him. It led to him building the largest social media influencer agency in the world (Elevator Studio), becoming an angel investor for 37 different companies, starting multiple mastermind groups, and launching an investment fund, as well as an investor syndication group, among many other accomplishments and ventures.

In this episode, we dig into Dan’s entrepreneurial journey and discuss the most significant lessons he learned from building and scaling multi-million dollar companies.

You’ll get to hear his framework for investing in startups, how he attracts investors and funds major deals by structuring unique terms, and the story of starting a modern sports card store during the pandemic that has done $18M in sales in the first year.

Key Takeaways with Dan Fleyshman

  • Placing “quarterbacks” in your businesses so you can accomplish more without sacrificing your time.
  • How Dan scaled a $15M clothing brand and took his energy drink public by age 23, becoming the youngest founder of a publicly traded company.
  • How his $65M online poker company failed overnight, and why it was the best thing that ever happened to him.
  • What it was like for Dan to get a $9.5M licensing deal with STARTER apparel.
  • Becoming the largest social media influencer agency in the world (Elevator Studio), and how Dan leverages this business to make equity deals with his clients.
  • Dan explains how he uses a “rolling fund” to raise capital. This is a fascinating disruption to the traditional fund model that allows accredited investors to commit with a lot less risk.
  • Learn about Dan’s investor syndication group (now 800+ members) and the criteria he uses to de-risk deals and invest in companies with big potential, including Sneaker Con, which was recently acquired by eBay.
  • Partnering with the world-famous DJ Steve Aoki and DJ Skee to open Cards & Coffee, a modern sports card store that did $18M in sales in the first year.
  • Raising capital using the “7, 8, 9 deal structure” and how Dan used this model to attract investors (including myself) and finance Black Site Ranch—an $8M commercial property with a ton of utility and perks!
  • Learn about Dan’s 100 Million Dollar Mastermind Experience AND the Avengers Real Estate Mastermind.

Free Gift

Dan's giving away 2 of his e-books.

  • How to Set Up Your Personal Brand for Under $1000” which is the ultimate blueprint to launch your personal brand.
  • How to Set Up Your Business for Under $1000” which provides essential strategies & tips you need to get started on your business idea quickly, affordably & effectively.

To get access to this gift, visit LifestyleInvestor.com/99

Want the Full Show Notes?

To get access to the full show notes, including audio, transcripts, and links to all the resources mentioned, visit LifestyleInvestor.com/99

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To get access to The Lifestyle Investor: The 10 Commandments of Cashflow Investing for Passive Income and Financial Freedom visit LifestyleInvestor.com/book

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