Internal Rate of Return Podcast

Ep 20. Corporate Leadership to Entrepreneurship with Financial Expert Cheryl Heller

Amanda Alexander Season 1

In this episode, the host sits down with Cheryl Heller, co-founder of the Strategic Board Collective and managing principal at Pillar One Consulting. Cheryl, who boasts over two decades of executive experience, discusses her journey from a long tenure at Capital One to becoming a fractional CFO and a partner at Clipper Ship Ventures. The conversation covers her real estate portfolio, including short and mid-term rentals, and how she vets investment deals. Cheryl also shares insight on managing financial operations for startups, the importance of networking, and transitioning from a corporate job to entrepreneurship. The episode concludes with advice on being in the right networks and mastering the balance between a scarcity and abundance mindset in financial planning.


00:00 Introduction and Guest Overview

02:21 Cheryl Heller's Real Estate Portfolio

03:11 Insights on Syndications and Underwriting

08:17 Managing Midterm Rentals

13:40 Personal Financial Journey and Mindset

20:48 Balancing Abundance and Scarcity in Business

22:43 Exploring Cheryl's Businesses

26:19 Exploring Fractional CFO Services

26:48 Specializing in FinTech, Real Estate, and Professional Services

27:56 Understanding Professional Services and FinTech

28:38 The Impact of FinTech on Daily Life

30:03 Cryptocurrency and Clipper Ship Ventures

30:49 Private Equity and Institutional Investors

38:23 Balancing Work and Personal Life

43:14 Transitioning from Corporate to Entrepreneurship

47:08 The Importance of Networking and Masterminds

48:50 Conclusion and Final Thoughts