Scaling to 8 Figures after Rejecting VC: Maarij Rehman on How to Win by Nailing Enterprise Sales

What does it take to scale to 8 Figures after rejecting VC?

After raising a $250,000 round and getting accepted into the prestigious Techstars accelerator, Maarij Rehman had achieved what most founders only dream of. But it was at this peak that the "love affair with investors had started showing cracks". He took the rare step of rejecting the Techstars offer and embarked on a path to return the capital he had already raised. This wasn't the story of a failed startup; it was the beginning of an anti-VC playbook for building a real business.

This mindset was forged years earlier when Maarij dropped out of university in his final term to start his first company. His initial idea—selling complex optimization software to large courier companies—collided with the reality of change management and union resistance. This failure led to a critical pivot with a new mission: if you can't help them, beat them at their own game by building a better, faster courier company yourself.

Freed from the VC pressure of hyper-growth, Maarij focused on what truly mattered: cash flow. In this episode, he shares the bootstrap strategies that allowed him to scale Envoi, including his proudest achievement: convincing Walmart to agree to Net 15 payment terms. He then reveals the audacious story of using a loophole in his convertible note agreement to buy out one of his institutional VCs and reclaim his company's destiny.

This is a masterclass in how to win enterprise sales, why patience is a bootstrapped founder's superpower, and how to scale to an eight-figure business on your own terms.

Agenda:

• The Unconventional Start: Dropping out of the University of Waterloo in his final term and how his entrepreneurial father became his first investor by funding the business with his final tuition payment.

• The Critical Pivot:

• The initial idea to solve the "traveling salesman problem" for large couriers like UPS.

• Why the idea failed: The profound lesson that a great solution is useless if your customer is fundamentally resistant to change.

• The pivot: Realizing "the guys that we're trying to help don't want to be helped," they decided to use their own tech to become a better courier company.

• The Anti-VC & Bootstrapping Playbook:

• The funding journey: Raising $250k from two institutional VCs after an initial investment from his dad and a pitch competition win.

• The turning point: Getting accepted into Techstars but rejecting their $120k funding offer because he had no clear path to deploying the capital effectively.

• The Buyout: How he spotted a loophole in the convertible note to buy out one of his VCs and regain control of the company's path.

• Enterprise Sales & Growth Strategy:

• How he got his first meetings with VPs at large companies by using the "student" angle on LinkedIn.

• Cash Flow is King: The single most important lesson was prioritizing payment terms over price. His proudest achievement isn't landing Walmart, but getting them to agree to Net 15 terms.

• The "Help Us, Help You" Strategy: How to leverage your performance to renegotiate terms with massive clients once you've proven your value.

• The Full-Circle Endgame: How, after years of competing, Envoi signed a strategic partnership with one of Canada's largest couriers, effectively turning their sales team of hundreds into Envoi's sales team.

Memorable Quotes

"Being profitable doesn't matter. Cash flow matters." 

"If you don't ask, you never get. That's been my motto for the last few years, just ask" 

"Make other people look good and you will succeed" 

"The problems that I have today are problems that I would have killed to have three years ago, four years ago, five years ago."