How Scott Leese Turned Self Doubt Into 16 Revenue Streams

Every sales leader has felt like a fraud at some point. That moment when you're sitting in the boardroom, nodding along as executives throw around acronyms you don't understand, wondering if everyone can see right through you.

Scott Leese not only felt this way … he embraced it. And that mindset shift transformed him from a sales rep with 7 months of experience into a serial entrepreneur with 16 revenue streams and 9 companies.

The Fraud Who Kept Going

"I felt like a fraud straight away," Scott admits about his first management role. 

"Like I don't know how I'm in a sales leadership role. I have seven months total sales experience."

But here's what separated Scott from the countless others who let imposter syndrome paralyze them: he kept going anyway.

While others wallowed in self-doubt, Scott developed a three-part framework that's driven his entire career:

1. Commit to Learning: "I was okay saying, 'I'm a fraud. I don't belong in this room yet. So I better study whatever I need to study so I do belong.'"

2. Eyes on the Prize: "I might feel like a fraud, but I still need to eat today. I still got to pay rent. I don't have time to sit around and wallow."

3. Perspective as Power: Drawing from his health struggles, Scott uses perspective as an anchor: "Nothing's going to be harder than being in the hospital for four years straight. This thing might feel difficult, but it sure beats nine surgeries."

The Bias for Action

What makes elite performers different isn't their lack of doubt… it's their bias for action despite the doubt.

"I think people overestimate others' memory of your own failure," Scott explains. 

"We could launch a brand new podcast today, and if it flops in two months, nobody will even remember we tried. We're not that important."

This perspective freed Scott to take calculated risks throughout his career, from leaving San Francisco sooner to building multiple revenue streams while still in corporate.

The Diversification Playbook

Scott's current portfolio includes 16 revenue streams across 9 companies but it didn't happen overnight. His advice for sales leaders stuck in golden handcuffs?

Start with the intersection of what you love and what makes money:

• Love real estate? Combine your sales skills with property investment

• Into fitness? Build a community that you can eventually monetize

• Fascinated by investing? Start building expertise while networking

"Find a buddy," Scott advises. "Rather than start a podcast by yourself, start one with a friend. 50% of something is better than 100% of nothing."

The Biggest Career Mistake

Scott's transparency about failure is as valuable as his success stories. His biggest career failure? Taking a VP role purely for the money without vetting the company.

"I did a lousy job vetting the founder, the executive team, the product, the market. This is a colossal mistake. I lasted six or seven months… it's the only blip on my resume."

The lesson? 

"I was very coin-operated. All I cared about was salary and OTE. I should have taken bigger swings… the difference between walking away with 500K versus 5 million from an exit is life-changing."

Your Next Move

Scott's journey from imposter to icon wasn't about eliminating self-doubt.. it was about acting despite it. As he puts it: "I like putting myself in rooms where I'm the dumbest person there because it forces me to level up."

The question isn't whether you feel ready. 

The question is: what are you going to do today to move forward anyway?