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  • Cory Cleveland

Consider This: Time Committed VS Failures Had

Is raising millions of dollars in capital the main indicator of success?


My name is Cory, I am the President of Creative Return and the host of The Insider’s Guide To Finance. The following are my insights and learnings from the interviews and dealings I have with talented entrepreneurs, operators, and financiers. I hope you find them valuable in your endeavours.


A number of interviews I have done shed light on an interesting path to success. That is time committed in a single company vs. failures through multiple ventures. For my argument here, raising millions in capital is an indicator of success.


This mini-revelation came to me as a couple of entrepreneurial guests I've interviewed have achieved noteworthy success but not of the overnight variety.


For example, Nic Beique, founder and CEO of Helcim raised $ 16 million in 2022 to continue the growth of his company. Another guest, Jason VandeBoom founder and CEO of ActiveCampaign raised $100 million in a Series B round to continue the growth of ActiveCampaign (coincidently, the email tool sending you this newsletter).


What these two, and many others have in common is they've been leading the same businesses they founded for over a decade. They started their businesses, not with a glamorous unicorn vision but with a common commoditized value proposition (a payments reseller and an IT development shop respectively).


What they had instead of a grand idea was the wherewithal to commit to their chosen industries and deliver value where they could. From this commitment came the identification and informed pursuit of growth that warranted validation and meaningful investment. In the case of Jason's company, the latest valuation is over $3 billion on a $240 million raise.


Contrary to this approach of long-term business building is the cliche approach of raising money and then failing fast. This approach does yield success, but with a lot more volatility, haste and waste. A lawyer friend of mine told me that most successful tech entrepreneurs have on average seven failures under their belt before achieving marketable success.


Perhaps my argument needs a better definition of success and failure, but it is worth celebrating those who choose to commit to the long run.


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