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The official CEO.com podcast featuring unfiltered conversations with the leaders shaping our world.
Clint Betts: Joe, thank you so much for coming on the show. It’s an honor to have you. You’re the Chief Growth Officer of Ampleo. Before that, you were at Homie. Give us a sense of your background and what Ampleo is.
Joe Grover: You bet.
I started my career as an entrepreneur running an agency. Then I spent seven years in venture capital at Mercato Partners.
After Mercato, I joined one of our portfolio companies as Chief Marketing Officer. I spent about 10 years as a venture-backed CMO, working across marketing and finance. One of those businesses was based in Denver, and while I was there, we merged with a company in New York.
I also spent some time as a turnaround CEO, which was tough sledding. Trying to keep companies alive and growing when the market shifts beneath your feet is incredibly difficult.
Eventually, I moved back to Salt Lake City from Denver and joined Homie as Chief Marketing Officer. We expanded the business and grew into five markets.
After leaving Homie, I took a sabbatical. I started playing more guitar, skiing more, and enjoying life. During that time, I stumbled into some consulting work doing fractional CMO engagements. That eventually led me to become a partner and owner at Ampleo.
Ampleo has been around for 30 years. Kent Thomas founded it, and this year we’re celebrating our 30th anniversary. Historically, the company focused on fractional finance services. If you were a startup that couldn’t afford a full-time CFO or controller, you’d call Kent and say, “I need a CFO,” and Ampleo would provide that expertise.
Three years ago, I launched the marketing practice and an HR practice. I built those divisions and now help expand the broader platform. We raised private equity last year, have acquired five companies, and will likely acquire more as we continue helping small businesses succeed.
Clint Betts: How does everything change in the age of AI? It seems like that’s what everyone is talking about. You’ve probably experimented with Claude, Codex, ChatGPT, and everything else. It feels weird out there right now.
Joe Grover: It really does.
I was in Dallas yesterday for a board meeting. We spent a few hours talking about acquisitions, integrations, growth strategy, and go-to-market plans. At the end of the meeting, the managing partner looked at us and said, “What are we doing about AI?”
It’s the right question.
Some of our work is already being automated, but most small and midsize businesses still haven’t figured out where AI fits. So the question becomes: how does Ampleo become the thought partner that helps CEOs understand how AI applies to finance, marketing, HR, and automation more broadly?
Like most leaders, I constantly feel behind because things are changing so quickly.
I was an early adopter of ChatGPT. I built custom GPTs for content creation, social media copy, and client communications. But every six months everything changes.
Today, Claude is where I spend probably 80% of my time. Cowork is another tool I’ve been leaning into recently because it helps automate work beyond the traditional prompt-and-response relationship.
For professional services, AI is a massive enabler.
Last week I was working with large datasets. Tasks that I would normally have done manually in Excel—building models, writing formulas, analyzing data—were dramatically accelerated by AI.
Our goal is to make sure our consultants are among the most AI-educated executives our clients work with. It’s not about forcing every company into the same AI strategy. It’s about ensuring our people understand the tools available and can use them to deliver better work in less time.
Clint Betts: Part of my question is this: you’re doing all these acquisitions. You’ve acquired five companies and you’re looking at more. What’s the calculus between buying versus building?
Joe Grover: It comes down to expertise and trust.
When someone hires a CFO, they’re not really hiring us for a balance sheet or a P&L. They’re not paying for reconciliations.
They’re hiring us for 20 or 30 years of executive experience.
They’re buying judgment, confidence, clarity, and wisdom.
Can AI automate activities? Absolutely.
Can it replace trust and executive counsel? I’m not sure.
When we evaluate new divisions and acquisitions, we think about which professional services categories are likely to be disrupted by AI. The question is whether we should avoid those areas or run directly toward them.
I think we should lean in.
If we’re on the forefront of disruption, we can provide significantly more value with fewer resources and lower costs. That’s an attractive position to be in.
Clint Betts: You mentioned that you’ve shifted from ChatGPT to Claude. I’ve experienced the same thing. I still use both, but I open Claude every day. Why do you think that is?
Joe Grover: I use everything.
I use ChatGPT for some things. I use Grok in my car. I’ve started using Perplexity more as well.
But I do a tremendous amount of content creation. I’m communicating all day long, and Claude simply does a better job for me.
Whether it’s collateral, board content, internal communications, or external copy, Claude consistently gets me 80–90% of the way there.
I also think the reasoning is stronger.
For data analysis and model building, I’ve found it more reliable than ChatGPT, although it’s certainly not perfect. The other night at 3 a.m. it generated a formula that was completely wrong. You still have to know what you’re doing.
Cowork is different because it moves beyond prompting. It organizes files, manages calendars, prioritizes communications, and helps automate workflows.
For example, I connected my text messages and had it identify high-priority conversations I hadn’t responded to. When you have hundreds of unread texts, that’s incredibly useful.
I still think we’re in the early innings.
Clint Betts: What does a typical day look like for you?
Joe Grover: As much as I love AI, I’ve had the same executive assistant for 16 or 17 years across four different companies.
Every morning starts with my kids and a family routine. Then, on my drive to the office around 7:45, I call Michelle.
She’s already triaged my inbox, Slack messages, and calendar. We spend 15 to 30 minutes reviewing priorities.
We have seven divisions, five acquired companies, and roughly 14,000 clients. There are always more things to do than time allows.
Obsessive prioritization becomes critical.
Michelle and I review everything and make real-time decisions. Sometimes meetings get moved because something more important emerges. Today, for example, I needed 30 minutes to clear my head before this interview.
After that, I review our ClickUp dashboards and AI-generated reports. We use a lot of ClickUp automation and agents. I can quickly see what’s completed, what’s behind schedule, and where attention is needed.
Then I enter a marathon of meetings.
Honestly, I spend a lot of time talking.
Clint Betts: Someone needs to invent a way to eliminate meetings.
Joe Grover: I agree.
I’ve started declining more meetings and relying heavily on AI note-taking tools.
Last week I had Claude review all my Fireflies meeting notes and identify everything I had committed to doing.
It found 65 commitments over a five-day period.
That was a little terrifying.
I then had it create a project plan and upload tasks into ClickUp.
The lesson for me was that a lot of work can happen asynchronously. Not everything requires a 30- or 60-minute meeting.
My calendar is still packed, but I’ve become religious about time blocking. I reserve non-negotiable blocks of time to focus and actually get work done.
Clint Betts: We use ClickUp too. How long until we don’t need SaaS tools anymore?
Joe Grover: It’s a fascinating question.
Right now, I have AI agents in ClickUp, automation in Claude, workflows in Cowork, and HubSpot connected to everything.
The three tools I use most are ClickUp, Claude, and HubSpot.
But eventually, I don’t think we’ll need this many separate systems.
ClickUp has a note taker. Fireflies has a note taker. Gemini has a note taker. HubSpot has its own AI assistant.
We’re surrounded by software that partially overlaps and only somewhat talks to each other.
At some point, I think much of that consolidates.
Clint Betts: What does the world look like six months from now?
Joe Grover: I have no idea.
The only thing I know is that six months from now, we probably won’t be talking about Claude.
Clint Betts: I think you’re right.
How do you think about leadership?
Joe Grover: Leadership is both art and science.
One thing I’ve learned is that leaders have to make difficult decisions.
As a recovering people pleaser, that’s probably been my greatest challenge.
Not everything can be decided by consensus.
Great leadership requires a clear vision that people can rally around, but it also requires the discipline to make hard decisions in service of that vision.
That means difficult conversations, restructuring, accountability, and tough feedback.
I’m currently reading The Courage to Be Disliked, which has been helpful.
I’m trying to accept that if I’m doing my job well, not everyone will love every decision I make.
Finally, leadership requires relentless prioritization.
The leader’s job is to take a vision, translate it into goals, and then translate those goals into daily activities that everyone understands.
Alignment is everything.
Clint Betts: What are you reading these days?
Joe Grover: I love Quit by Annie Duke.
I’m obsessed with failure because I think most entrepreneurial lessons come from failure, not success.
We celebrate successful CEOs constantly, but some of the most valuable lessons come from mistakes, collapses, and setbacks.
Quit challenges the idea that persistence is always the answer. Sometimes stopping is the right decision.
I also loved Die With Zero, which completely reframed how I think about wealth.
Recently I read The Art of Spending, and my wife had me read Let Them by Mel Robbins, which was phenomenal.
I’m constantly listening to audiobooks.
I also no longer feel obligated to finish every book. If I get the core idea and it’s not pulling me in, I move on.
Clint Betts: What do people get wrong about marketing?
Joe Grover: They try to do too much.
Marketing gives you endless options, but you can’t do everything.
A lot of companies spread their budgets across too many channels. They’re trying a little LinkedIn, a little Google, a little radio, a little TV, a little out-of-home.
When I see someone buy one billboard, I usually think that’s not enough.
I’ve spent millions of dollars on billboards across multiple states. One billboard by itself rarely moves the needle.
The most effective strategies are usually more focused.
Instead of spreading resources across 20 channels, win in a few.
Clint Betts: Tell me about your podcast.
Joe Grover: It’s called The Real F Word.
The F stands for failure.
I launched the first season last year, and I have more episodes coming.
There’s no business objective behind it. It’s a labor of love.
For me, it’s entrepreneur therapy.
I talk with founders who have lost millions of dollars, shut down companies, fired employees, lost relationships, and experienced profound setbacks.
What I wish I’d known earlier in my career is that failure doesn’t define you.
A bad quarter doesn’t define you.
A failed company doesn’t define you.
A poor hiring decision doesn’t define you.
What actually defines you is the accumulation of those experiences.
The hope is that all those experiences increase the probability of future success.
That’s what the podcast explores.
Clint Betts: I worry about the mental health of our community.
Joe Grover: Me too.
Ten years ago, I had to tell investors they had lost all their money. At the time, it felt like the end of the world.
I didn’t know anyone I could talk to about it.
That experience eventually led to conversations with people like Bubba Page, who became my first podcast guest.
We even joked about creating a “Fail Club,” where membership required losing at least a million dollars.
The point wasn’t to celebrate failure. It was to normalize it and learn from it.
Clint Betts: Finally, we end every interview the same way.
At CEO.com, we believe the chances one gives are just as important as the chances one takes.
Who gave you a chance that helped get you where you are today?
Joe Grover: Alan Hall and Greg Warnock.
Back in 2005, I participated in a program called Hunto, one of the earliest startup incubators around.
It was happening around the same time as Y Combinator and Techstars.
Alan and Greg invested money, education, and confidence into a group of young entrepreneurs. Brock Blake and I were part of the same cohort.
Most of our companies failed. Lendio was the exception.
But that experience changed everything for me.
Later, Alan and Greg gave me an opportunity to work in venture capital. I had absolutely no business being in venture capital.
I spent six months working for free, calling institutional investors on the East Coast and helping raise capital.
They saw something in me before I saw it in myself.
That opportunity led to seven years in venture capital, exposure to incredible entrepreneurs, and relationships that shaped the rest of my career.
I’ll always be grateful for the chance they gave me.
Clint Betts: Joe, thanks so much for coming on. Let’s do this again sometime.
Joe Grover: Thank you, Clint. I really appreciate it.
Clint Betts: Thanks, my friend.