Luke Cannon: A Timeless Entrepreneur

Issue 08

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It’s Thursday, June 17, 2021, and this week’s founder is Luke Cannon:

  • A Versatile education

  • Marketing + Analytics, but not together

  • His current side project and new job

  • Luke’s Advice

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Luke's Story

A brief history

Luke, like many others, entered college without a big plan ahead of him. He liked business, and so enrolled in the business school.

Unfortunately for him, he wasn't all that interested in the early classes, so he worked his way through courses like art history before coming back to economics and the liberal arts.

Luke never truly moved away from business, though. He learned early on that each year his school held a business plan competition. Each year, Luke entered with a new idea – he and a team would scope out their business, write a plan, and present the idea to a committee of successful entrepreneurs or professors.

The competition allows alumni to return and continue to compete after graduation, so Luke continued to compete.

He's never made it past the second round of the competition.

Luke is working to prove their judgment wrong. We'll get to his latest project, Timeless, in a bit.

Straight into Startups

Luke considered going into consulting, even making it into later rounds of the interview process at a few firms. After gaining an offer at a startup in Washington D.C. he couldn't turn down, his path was set.

Luke worked for a startup creating an education product that focused on students learning to, wouldn't you know it, consult! His team consisted of around 40 people and, as a small company, allowed him to learn a lot about a ton of different roles.

Luke fell into marketing almost by accident, but he loved it from the start. Paid ads, some content marketing, and other tactics came quickly to him.

Covid threw a wrench in the operations though, leaving Luke and 36 of his coworkers without a job.

Off to the Uber for … plumbing?

Luke was engaged, his fiance lived in Chicago, and he wanted to eventually move there. Opportunity galore! One of his old bosses set him up with a company building a home services marketplace. If you needed a plumber, they would get one sent to you.

The timing was perfect. The company was growing rapidly, thanks to Covid and their new offering for remote service. Call a technician, show them the problem, and they'll try to help you solve it. Less time, less cost, more convenience!

Luke didn't get to work in marketing while he was there, however, and though he learned a ton about analytics – SQL, Tableau, and the ideas around them, it just wasn't his preferred path.

He's jobless! (not really)

Luke always had his vision to start his own thing. He was building an audience on LinkedIn, getting serious about making connections on Twitter, writing a newsletter, and starting his own project called Timeless.

Timeless is still in development, having just been opened up to a wider audience for testing this week (yours truly is in that first cohort!). The idea centers around your tweets having value, even long after they've been forgotten. Sign in, select tweets you want to resurface months later, and Timeless automatically posts them again for you.

See! Not jobless

Luke has been keeping it a bit of a secret, but he's now working in marketing again at a company called Magic. They're doing password-less logins, a true revolution in the technology world. Imagine no longer having to come up with a different password for each site. Or, more likely, not being shamed for continuing to use the same password you used in college!

Luke's Advice

  • Find your niche. Once you've done that, go a little further. You have to truly understand your piece of the puzzle to be highly successful.

  • Take big risks! There's no reason, especially in your 20's and 30's, not to do so. That's the only way to win big.

  • If you don't win, bet big again. Stretch to the very edge of your risk-tolerance level. Don't let one failed bet make you play it 100% safe for the rest of your life.

  • Analytics is a bit overrated in the marketing world, especially for startups. Learn the frameworks that work and stick with them!

You can connect with Luke through Twitter as @lukecannon727 or on LinkedIn. Check out to start showing off your old content again.


Procrastineur” is a newsletter about entrepreneurs’ successes and struggles, written by Will Whittenton. You can connect with me through my website, Twitter, LinkedIn, or send me an email at If you enjoy the newsletter, please share!

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