Most of us start a business to get our time back, and somehow end up the one person it can’t run without. In this Substack Live I sat down with Cory Blumenfeld, a five-time founder who built a virtual assistant company called BlueMoso, on how to stop being the bottleneck in your own company. We get into why the system usually only exists in the founder’s head, how to hire for the match instead of just the skill, and the line I keep coming back to: AI is for tasks, people are for outcomes.
Watch the full conversation above.
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Outline
(00:00) – Intro: who Cory is and how he got to Substack
(01:20) – Why human content is becoming a premium tier
(01:56) – Five businesses, zero experience, and learning by building
(08:42) – The founder bottleneck: leading from the backseat
(10:06) – If you got sick tomorrow, would the business survive?
(14:28) – Type-A founders, trust, and hiring for the match
(16:46) – The hiring framework: skill, work style, communication, personality
(20:03) – VAs are for outcomes, AI is for tasks
(22:10) – Humans with AI, not AI versus humans
(23:25) – Everyone is starting at zero with AI
(33:49) – Why he named it Taking My Time Back
My Takeaways
The founder is the bottleneck. So the whole conversation really starts here. The minute a company can’t survive without the founder in every decision, the founder has stopped leading and started blocking. Cory said it about as bluntly as it gets:
“Any founder, any CEO trying to lead from the backseat drives the car off the road.”
I’ve watched this one up close, and the test I keep coming back to is simpler than people want it to be. If it’s all hinging on you, you’re not leading well, you’re just busy.
The system only exists in your head. Here’s the part founders hate to hear. When delegation fails, we blame the hire. Cory’s take is that the real problem is upstream, because the playbook never left your head. He fixed it by writing his whole content process down so completely that his assistant couldn’t fail.
“I documented my strategy, made it super clear so they couldn’t fail. I set them up for success, and it started working.”
That reframed it for me. The bottleneck usually isn’t your team’s ability, it’s the stuff you’ve never bothered to get out of your own head.
Hire for the match, not just the skill. When I asked Cory how he actually trusts people enough to step back, he didn’t start with skill. He started with fit, work style, communication style, personality, and then skill.
“Hiring someone is not just skill alone. What’s their work style? What’s their communication style? The match is everything.”
And he was honest about why most of us struggle with it. A lot of founders are type-A with trust issues, me included on some days. If you hired someone for a skill you don’t have, the worst thing you can do is hover. Give them the room to be good at the thing you brought them in for.
AI is for tasks, people are for outcomes. This is the line I’ll be repeating for a while. Cory draws a clean line between what you hand a person and what you hand a machine.
“You don’t bring in a virtual assistant to work on a task. You bring them on to deal with an outcome. You bring on AI to deal with individual tasks.”
I told him on the spot that’s a quote CEOs could put on their walls, and I meant it. It also points at where this is going. When everyone has AI doing the repetitive work, the human part, the judgment, the relationship, the actual experience, stops being the cheap part and becomes the premium one.
Figuring out where AI fits and where your people have to stay is most of what I work on with the leaders I coach. If you want to talk it through, my calendar is here.
One Question to Sit With
If you got sick tomorrow and unplugged for two weeks, would your business still be standing when you got back? Sit with the honest answer.
Watch the full conversation above, and go subscribe to Taking My Time Back, Cory’s Substack on helping founders win their time back.
About Cory Blumenfeld
Cory Blumenfeld is the Founder and CEO of BlueMoso, a managed virtual assistant service for founders, executives, and agencies, with a vetted talent pool of more than 70 assistants and specialists. He’s a five-time founder with two exits across health tech, fintech, and outsourcing, and he runs his companies remotely from Playa del Carmen. He writes Taking My Time Back on Substack.
About me
Joel Salinas is an Executive AI Coach for leaders at small and mid-sized businesses and nonprofits. 1:1 coaching, team workshops, and AI strategy work built around amplifying what your team is already good at. Creator of the AI Leadership Triad. He writes Leadership in Change. If you want help thinking through your own AI strategy or online presence, start here.
Written by a human, for humans.
Thank you Ankita Chatrath, Janet Macaluso, and many others for tuning into my live video with Cory Blumenfeld! Join me for my next live video in the app.
