256: Why Waiting to Feel “Ready” Is Killing Your Potential | Valerie Bowden
Release Date:
December 11, 2025
Release Date: Dec 11
What happens when you decide not just to dream of adventure, but actually buy the one-way ticket? On this inspiring episode of the Learn-It-All™ podcast, host Damon sits down with Valerie Bowden—social worker turned multi-startup founder and CEO of Cradle—to unpack a journey that defies the expected. Tired of the 9-to-5 grind, Valerie quit, moved to Ethiopia, and learned (sometimes the very hard way) that resilience, self-trust, and the ability to do hard things daily are the ultimate leadership skills. Together, they cover what travel really teaches us, the raw reality of failed startups, and how reframing failure builds grit—even sharing lessons learned from devastating mistakes with cash flow and investors.
From building confidence with daily risk-taking to why creating jobs (not just charities) drives change, this episode is packed with real stories, unfiltered advice, and practical takeaways—whether you’re a first-time founder, a corporate escape artist, or simply need permission to take the leap.
What You’ll Learn:
What travel teaches you that a classroom can’t: How leaving her comfort zone built Valerie’s confidence, adaptability—and a lifelong ability to handle pressure.
Why failing forward is the only way: Valerie shares her hardest startup lessons and how to reframe failure as “winning or learning.”
Tips for handling extreme pressure: The mindset shifts and practical boundaries that keep leaders strong under stress.
Outsourcing secrets for faster growth: When, why, and how to find (and train) the right offshore talent—and avoid common mistakes.
Who should (and shouldn’t) start a company: Valerie’s clear-eyed advice for anyone considering the jump from corporate to startup founder.
How to grow leadership as you scale: The processes, mindset, and relationship-building moves that matter most when you go from solo to 120 employees—and beyond.
In This Episode:
00:00 – Valerie’s take: “Travel is the most responsible thing you can do”
00:57 – Meet Valerie Bowden and her leap from social work to Africa
02:24 – Where’d the courage come from to quit and travel solo?
04:01 – Family and society’s doubts—how Valerie handled no support
05:11 – Hard-won lessons learned backpacking Africa
06:16 – Why jobs, not charity, create lasting change
07:26 – Startup attempts (and failures) in Ethiopia
08:33 – Separating self-worth from startup outcomes
09:29 – Valerie’s advice for finding your identity after failure
11:02 – The nightmare investor story—and lessons learned
12:57 – Masterminds, mentors, and not going it alone
13:59 – Launching Cradle… at 8 months pregnant
15:23 – There’s never a “right time” for a leap
16:00 – Valerie’s practice: doing something hard every day
18:18 – How to stop caring what other people think
20:13 – What the corporate world did teach Valerie after all
21:18 – Who should—and shouldn’t—become a founder
23:26 – How Valerie handles the pressures of leadership
25:17 – The $25k lesson: why good cash flow is non-negotiable
27:03 – What Cradle does and how it’s disrupting outsourcing
29:39 – How and when to outsource (without the usual pitfalls)
34:09 – Scaling from 20 to 120 employees—new leadership, new processes
36:16 – Is AI a threat or an asset for outsourcing teams?
38:49 – Cradle’s vision for 10,000 Africa-based team members
40:10 – What Valerie hopes her daughter learns from her journey
41:44 – Small steps—the only way to big leaps
About Valerie Bowden
Valerie Bowden is the founder and CEO of Cradle, a U.S.-Africa outsourcing business that helps American companies unlock affordable, skilled talent across the African continent. After burning out in her corporate job, Valerie Bowden bought a one-way ticket to Ethiopia, backpacked solo across Africa, and never looked back—eventually living there for eight years and launching multiple startups. Along the way, she discovered the power of jobs over aid, survived failed ventures, learned tough lessons from investor stumbles, and built Cradle into a thriving, seven-figure business with 120 team members. Valerie is passionately committed to changing the narrative around Africa, job creation, and what it means to be a resilient, purpose-driven leader.
Resources Referenced:
Crdle.com – Valerie’s company (site includes a lead magnet on outsourcing)
