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Today, I’m joined by Joe Stolte, a serial entrepreneur, growth coach, and the CEO of Daily.ai, a company that helps brands publish AI-powered email newsletters that generate 40-60% open rates without writing a single piece of content.

As a program manager at Microsoft in his 20s, Joe was making over $250,000. But as an entrepreneur at heart, he knew he couldn’t ignore the call to go out on his own. After his first attempt at raising outside capital left Joe $37,000 in debt, he learned from his experience, going on to found 5 companies and exit 3.

Joe is also a former Inc 500 entrepreneur who helped create a $60M+ exit at GrowFlow, helped take Lottery.com public at $526M, and helped grow Tractionology Group to producing $44M in client revenue in 3 years.

In today’s episode, you’ll hear Joe’s firsthand experience about the pros and cons of bootstrapping vs. fundraising. You’ll also learn a step-by-step process for fundraising (even if you don’t have high-powered connections), how to set up powerful introductions to investors with deep pockets, and how to use AI to boost your revenue — not just your dopamine.

Inspiring Quotes
  • To get great at something, you have to play the tape back and make one improvement and then try again.” – Joe Stolte
  • I’d rather be patient for the right chess move than just barf all over the situation or move too quickly. I want to move more like an orca and less like a piranha at this stage of my career.” – Joe Stolte
  • To me, the core of business is asking how can I behave slightly more like a detached scientist that’s just interested in running 10,000 experiments until I crack them.” – Joe Stolte
  • “The absolute worst is rarely going to happen. Plan for the likely worst-case scenarios.” Joe Stolte
  • I’ll never do another venture-backed company again. I want to play my game.Joe Stolte
  • Raising money creates the ability to create a bigger outcome faster.Joe Stolte
  • I think AI is as transformative as electricity.Joe Stolte
  • f you can get around a great leader and absorb what they’re great at, you will shortcut so much of your journey.Joe Stolte
  • Get comfortable asking for help, because you are going to need a lot of it all the time for the rest of your career, and that’s a muscle worth building.Joe Stolte

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