From Sales Rep to Boostrapped SaaS founder: Jesse Ouellette, founder of Leadmagic

Ryan is joined by bootstrapped SaaS founder Jesse Ouellette in this episode. Jesse talks about how the pandemic presented the perfect opportunity for the creation of Leadmagic, a website identification tool and talks about how you can turn your knowledge into revenue as well as what 99% of companies are missing in their outbound email activity.


  • It was after losing his job and feeling frustrated that Jesse decided he wanted to run something of his own. He started off consulting and then during the pandemic bootstrapped his own SaaS company, Leadmagic.
  • The pandemic presented a unique opportunity, Jesse had much more time on his hands and decided to spend that time learning more about software and this enabled him to go into the market.
  • There is space for more than one product in a market and Leadmagic prides itself on its accuracy, even if its appearance and UI aren’t the most polished.
  • Jesse’s sales background has allowed him to pre-empt and identify his client’s current and future needs with accuracy.
  • If you keep your cost of sales down but your product proposition value high, then you will be able to scale quickly and efficiently whilst keeping your customers happy.
  • Being an entrepreneur and founder isn’t easy, no matter how it is often sold, there are no quick wins, it’s hard work and it’s difficult.
  • To turn your knowledge into reoccurring revenue, you need to build an asset. You then need to find a way for people to interact with this asset before purchasing anything.
  • 99% of companies don’t have a plan in place to deal with the downsides of sequencing tools. So much of their outbound traffic is being lost to spam filters.


“You can have more than one product in the market”

“I know what people need, I have a good sense of that”

“If you’re gonna charge people, you’re gonna charge them on impact”

“You’re jeopardising your future as a start-up”

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Ryan Staley

Founder and CEO

Whale Boss




How do you grow like a VC-backed company without taking on investors? Do you want to create a lifestyle business, a performance business or an empire? How do you scale to an exit without losing your freedom?
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