Ryan Westwood: Slow Down to Speed Up, Investing, $250M Exit

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Ryan Westwood: Slow Down to Speed Up, Investing, $250M Exit

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In this episode of the Startup Ignition Podcast, we sit down with Ryan Westwood, a prolific entrepreneur and investor who recently scaled Simplus from zero to 600 employees and sold it to Infosys for $250 million. Ryan shares his incredible journey from weeding gardens to earn his first pair of Air Maxes to executing a massive "roll-up" strategy in the Salesforce ecosystem. We dive deep into the mechanics of acquiring companies to increase valuation multiples, the importance of "slowing down to speed up," and how he is applying his playbook to his newest venture, Fullcast. Ryan also opens up about family philanthropy, the discipline of meditation, and the relentless mindset required to win.

(00:00:00) Introduction to Ryan Westwood and his $250M exit

(00:02:06) Reading Ryan’s bio: Entrepreneur, Investor, and Philanthropist

(00:04:07) Startup Mad Libs: "Venture Capital is your enemy"

(00:05:52) The biggest startup killer: Premature scaling

(00:10:24) Ryan’s 4 rules for investing in a company

(00:11:00) Angel investing and focusing on building Fullcast

(00:15:21) Earning Nikes at age 11: The reward of hard work

(00:20:34) Shifting from tech to revenue generation

(00:24:36) Living on $1450/month to save capital for the first startup

(00:28:37) The origins of Simplus and identifying the CPQ opportunity

(00:31:20) Finding a niche in Salesforce customization

(00:33:57) The "Roll-up" Strategy: Acquiring 7 competitors in 3 years

(00:38:07) The current state of Private Equity and finding buyers

(00:41:12) Using a mix of debt, equity, and cash for acquisitions

(00:43:11) The paranoia of closing a deal during the onset of COVID

(00:47:42) Using a Series C "Blocker" to negotiate a higher price

(00:49:42) Why Ryan left Infosys despite a $150M EBITDA year

(00:51:58) Drafting off the Salesforce brand and staying differentiated

(00:53:20) "Jab, Jab, Right Hook": Giving value before asking for the sale

(00:55:03) Networking and the power of being a good person

(00:59:55) The Fullcast story: Buying a company to fix sales operations

(01:01:19) Rolling equity and doubling down on the new venture

(01:02:08) Growing Fullcast valuation to $125M in seven quarters

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