71 Josh Cheng: How A CFO/COO Delegates, Hires, and Stays Sane as a Founder

Send us Fan MailWhat happens when your former client comes on the mic to talk about delegation, leadership, and what it’s really like working with a powerhouse EA?In this conversation, CFOO and strategic operator Josh Cheng joins Bonnie to unpack their years working together at Verity, how he thinks about delegating as a founder, and why humility might be the most underrated leadership skill in business.Josh shares his journey from UC Berkeley to nonprofit financial counseling, wealth management, startup co-founder, and now fractional CFO/COO for founders, firms, and nonprofits. He and Bonnie talk about how they built a high-trust working relationship, what it looks like to treat your VA or EA like a chief of staff, and how that changes the way you lead.They also dive into sabbaticals, AI, and the messy middle of being a small business owner or fractional leader…the part where your brain feels like it’s carrying everyone and everything at once.If you’ve ever wondered:“Do I really need a COO or CFO right now?”“How do I know if a client or team member is actually good for my mental health?”“Can I trust someone else with my calendar, priorities, and big picture?”…this one is for you.You’ll hear Josh and Bonnie talk about:How they met through a holding company, and why that structure created multiple opportunities for VA support across subsidiariesWhy Josh always saw Bonnie as a strategic partner and not “just” an assistantWhat it practically looks like to treat an EA like a chief of staffUsing delegation and fractional roles as a talent pipeline before hiring full-timeHow to know when to fire a client that isn’t aligned with your values or energyWhy is humility a core leadership value if you want to delegate wellThe magic of sabbaticals…and how stepping away actually made Josh more creative and strategicThe tension of being the founder, where, yes, “it all rolls uphill.”Why your network is gold, especially in the age of AIBy the end, you’ll have a clearer lens for evaluating who you work with, who supports you, and how to build a high-trust team that lets you lead without losing your mind. #Productivity #Delegation #Leadership #CFO #COO #FractionalLeadership #EntrepreneurLife #Founders #Sabbatical #AI #Teams #Trust Support the showGet your D2E Swag Here Find us on:D2EGSD on Youtube:D2EGSD Website:LinkedIn:Spotify:Find Your Service ProKeywords:#Productivity#Delegation#Outsourcing#Productivity#Leadership   #Viral