Discover how a chef-turned-entrepreneur built successful online businesses, overcame self-doubt, and grew a digital empire by creating value and saying no to perfectionism.

Guest:

Oliver Kenyon — Serial Entrepreneur, Managing Director & COO at Lovecars.com; Co-founder of Landing Page Guys and Fix Forums

Blog/Social: oliverkenyon.com | @OliverKenyon

What does it take to go from working nights as a teenage chef to running thriving digital businesses with tens of thousands of users? In this candid, practical, and inspiring interview, Oliver Kenyon joins Rebelhead Entrepreneurs to share his unconventional entrepreneurial journey — from launching his first website at fourteen to managing multiple companies. Listen as Oliver and host Adam talk through the realities behind “overnight” online success, why self-belief is non-negotiable, and how to handle perfectionism before it paralyzes your progress.

You'll hear Oliver’s hard-won lessons on personal branding, finding co-founders who complement your skills, and structuring your days for peak productivity. He dives into the importance of resilience, the danger of credit-fueled startup lifestyles, and how creating something of true value should always come before chasing the money. Whether you’re pondering a leap into entrepreneurship or struggling to balance multiple projects, this episode offers timeless advice on habits, mindset, and the power of just getting started.

Note: This podcast is no longer active and was originally published before 2016. Links and contact details may be out of date, but the conversation still holds valuable insights today.

Key Points

• Oliver shares how his first entrepreneurial spark ignited on hip-hop forums as a teenager (04:21)
• Why personal branding outlasts any one business or project (47:12)
• The pitfalls of perfectionism — and how shipping imperfect work leads to growth (56:14)
• Strategic use of side hustles: Keeping a day job while scaling an online business (28:50)
• Building companies with complementary co-founders and why skill alignment matters (40:15)
• Networking as the true source of big opportunities (43:36)
• Why “get shit done” is Oliver’s enduring mantra for productivity (107:47)
• How to manage your time and focus when juggling multiple ventures (109:35)
• The value of saying “no” — and when to shift from yes-man to gatekeeper (16:24)
• Dealing with criticism, friends who don’t understand, and rebelling against conventional wisdom (50:55, 121:19)

1. Ship before it’s perfect. Don’t let perfectionism stall your momentum — learn as you go, course-correct, and build in public.
2. Build personal resilience and ignore naysayers. Self-belief and strong work ethic will carry you further than initial skills or resources.
3. Prioritize value and relationships over quick wins. Lasting success comes from helping others, cultivating your brand, and picking the right partners and clients.

• Oliver Kenyon’s blog: oliverkenyon.com
• Basecamp project management (basecamp.com)
• Rework by Jason Fried & David Heinemeier Hansson
• KnowEm username checker (knowem.com)
• Pat Flynn’s Smart Passive Income (smartpassiveincome.com)
• Zach Johnson: blogging.org
• Lovecars.com

“I’ve always wanted to kind of do my own ideas and see my kind of visions take place. Believe in yourself and kind of stick to what you’re doing and everything else will follow.”

“The fear of failure is kind of what keeps me working until God knows when in the morning. Get shit done.”

“If people take the piss or if people put you down, then they really shouldn't be your friend. You have to move on and surround yourself with the right people.”

“Don’t ever email me from a Gmail account — get your own domain, take yourself seriously, and make your brand consistent everywhere.”

“If you believe in what you’re doing and you stick to it and you don’t worry about the money … the money will follow.”