TWO EXITS. AND MORE YET TO COME…

ft. Ryan Atkinson

Ryan Atkinson, serial entrepreneur and investor, joins Raman Sehgal to unpack the repeatable playbook behind two successful exits in recruitment and professional services. They explore how A player teams, quality clients, and contract revenue created scalable, cash flowing businesses, why competitive tension changed the second sale process, and what happens after you achieve financial escape velocity but still feel the pull to build again.

IN THIS EPISODE

In this episode, Raman Sehgal sits down with Ryan Atkinson. Ryan is a serial entrepreneur and investor with more than 25 years of experience building, scaling, and successfully exiting recruitment and professional services companies. He’s co-founded and led some of Canada’s fastest-growing staffing and technology firms, including Redwood Global, Direqlink, and CORE Resources, a national leader in IT staff augmentation and Agile consulting.

Known for his ability to spot market gaps and move fast, Ryan has built businesses through every phase of the cycle—startup, hyper-growth, acquisition, and integration. He grew Redwood Global from two founders to $30 million in annual revenue, earning multiple PROFIT 500 awards before selling to S.i. Systems. At CORE, he helped hundreds of enterprise clients modernize their workforces through Agile transformation and cloud-based staffing models.

A lifelong problem-solver, Ryan’s superpower is turning complexity into clarity—whether that means building go-to-market engines, scaling sales teams, or closing the deals others can’t. He leads with energy, candour, and a bias for action, helping founders and executives push through the noise to execute.

Ryan Atkinson – Rylora Ventures

WHAT WE COVER

How building A player teams and A list clients became the repeatable playbook behind two high growth exits
Why contract staffing created defensible, cash flowing annuity revenue that drove valuation
The difference between selling exclusively the first time and creating competitive tension the second time
What it really takes to be diligence ready, from clean books to ironclad client and contractor agreements
The bucket of money versus cash flow dilemma that hits after exit
Achieving escape velocity financially, yet still feeling the pull to build again

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Ryan Atkinson

Ryan is a serial entrepreneur and investor with more than 25 years of experience building, scaling, and successfully exiting recruitment and professional services companies. He’s co-founded and led some of Canada’s fastest-growing staffing and technology firms, including Redwood Global, Direqlink, and CORE Resources, a national leader in IT staff augmentation and Agile consulting.

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