Ross Lipson is a true serial entrepreneur who has made it both by bootstrapping and raising capital. He’s what Amazon is to books for the food and cannabis industry. He’s still only 33 years old.
During our interview on the Dealmakers Podcast, Ross Lipson shared his journey from young hustles to dropping out of college, to selling multiple companies and now scaling a third. Plus, his tips on what it takes to get a scrappy startup off the ground, setting your company up to scale, why all entrepreneurs should take a road trip, and how his new business has grown 700% thanks to COVID-19.
Ross Lipson credits a lot of his success to both parents and growing up in Southeast Michigan.
His mother is a therapist who he thanks for being incredibly supportive of all of his decisions over the years. Including dropping out of college after just one week.
His father is an entrepreneur who has been running his own successful business for more than 35 years. He instilled the foundations of entrepreneurship in Ross and his brother Zach from a young age.
They were taught there were no limits, and whatever they dreamed they could achieve. He says the hard part of being an entrepreneur is just getting started. It’s not a lack of ideas. It is that 99% of people never take action on them. With their dad that wasn’t an option. He taught them confidence, and to just take the next step. Including taking them to an IP attorney when he was just around 10 years old.
That spawned many early side hustles. He tried everything from going to Sam’s Club with his mom and then breaking down the candy and reselling it to his friends at school, to colognes and burned CDs, to Pokemon cards.
Ross says he did well enough at school, but it just wasn’t what interested him.
It was only a matter of days at Michigan State before he fell in with some other entrepreneurs and started hustling on his first real startup.
It was food delivery for students. Well before you heard of uber eats. They bootstrapped it and got scrappy. Since most people didn’t have computers they went door to door to restaurants. They would drop off fax machines and say “just let me send you orders.”
To get the orders they would be up at 4 am breaking into school classrooms. They would take over the chalkboards with their ads, or plant flyers in the library. It was work, but it worked.
Setting Up to Scale (Or Not)
Lipson has learned a lot about scale through his various ventures.
One of the things he seems to have consistently gotten right was taking on a new market right before it inevitably exploded.
He also learned some of the things which can prevent you from achieving real scale.
They grew the company quickie to multiple universities, kind of like Facebook. Only they had different operating names at each one. At Michigan State, they were Go Green. At the University of Michigan they were Eat Blue, and so on. They also had partners at each school which owned a piece of their market. It was too fragmented.
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