OhHello - a show about non BS career mentorship and expert advice OhHello - Allison Whalen of Parentaly
It's episode 95 of the OhHello pod and this founder/CEO is not only wicked smart, but
Everyone loves the “big leap” founder story.
But the truth?
The best companies aren’t built on leaps.
They’re built on small, smart, disciplined hops — over and over again.
Allison Whalen, CEO and Founder of Parentaly, joined Jeremy Bloom of OhHello to share what scaling a real company actually looks like:
- Why smart founders de-risk their bets before they jump
- How doubling her pricing (thanks to the right mentor) shifted her company’s trajectory
- The emotional pressure of building when it’s personal — and how boundaries create better leaders
- How “worst-case scenario thinking” can actually fuel, not freeze, growth
This conversation isn’t just about parental leave — it’s a blueprint for how real resilience is built.
If you’re building, investing, or mentoring the next generation of founders, this is a must-listen.
🎧 Full episode now live.
Massive thanks to Allison for keeping it honest, smart, and actionable.
#startups #founders #resilience #riskmanagement #venturecapital #ohhello