Welcome to Founder Real Talk, a podcast for founders, by founders.
We explore the real journey of building and growing a company. Each episode, we go beyond the highlight reel to unpack the strategies, decisions, and hard lessons that shaped successful businesses, revealing the good, the bad, and the ugly behind the growth.
This week, Josh sits down with Eric Elwer, CEO and founder of SteppingStone, an AI-native platform connecting students, universities, and employers around real outcomes. Eric breaks down why the way colleges measure career readiness is broken (“it’s like checking the patient after they’re in the mortuary”), the personal moment that sparked the company (watching his own daughter brought to tears by bad university tools), and the gutsy decision to scrap V1 of the product entirely and start over — a call that led investors to double down with 2x the round. He gets honest about the hardest transition of all: going from building a great product to building an actual business.
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Chapters(00:00) - Intro
(01:35) - The problem: measuring career readiness after it’s too late
(03:17) - Why this is personal: watching his daughter Sydney in tears
(06:22) - A big win: scrapping V1 and starting over
(08:19) - Why he chose a hard reset over a tweak
(09:56) - Wisdom is failure redeemed: building a product vs. building a business
(15:57) - The biggest challenge now: fundraising and the startup pinch
(19:38) - “Can I afford to grow?”
(20:27) - Evolving as a leader: doing the jobs that aren’t your strengths
(22:59) - The growing edge: learning to go from product to business
(27:40) - Investing in himself: the spiritual side of avoiding burnout
(30:58) - Eric turns the mic on Josh: how do you prepare someone for this?
Links & ResourcesReferenced in the episode:
- Grand Canyon University
- The Energy Project’s four-energies framework: mental, physical, emotional, spiritual
Keywordsfounders, entrepreneurship, edtech, career readiness, higher education, AI-native platform, SteppingStone, Eric Elwer, university outcomes, student success, product pivot, starting over, product to business, startup pinch, fundraising, customer acquisition cost, founder burnout, spiritual energy, leadership transition, first-time CEO
