David Mosberg, of Triumvir Financial, has looked inside the books of roughly 250 companies over 25 years, and he shares what that view reveals about small business owners. He explains that many owners live out of their company through distributions, then wonder why a profitable P&L leaves no cash. He argues that founders should treat payroll, marketing, and technology as investments measured by ROI rather than costs to be squeezed. Mosberg also describes Casper Workflow Strategies, a company he started with his son Levi to build AI tools for small businesses, and a public challenge to reach $100,000 in profit in six months. He covers how AI moved from curiosity to agentic tooling in his work, why relationships should never be fully automated, and how discovery conversations won his first clients. He closes with practical advice: set up a twice-daily email recap, put profit on the dashboard, and only read financial statements if you plan to act on them.
After seeing inside 250 companies' books, David Mosberg says most owners miss the same thing: they are living off the business.
What pattern do struggling businesses almost always share?
Owners live out of their company. They pay the mortgage and lifestyle with company money, and it shows up as distributions on the balance sheet. The P&L says we made a quarter million, but there is no cash. The company did not do badly, the self-discipline did.
What do owners consistently believe about their own numbers that is not true?
Many have a scarcity mindset and see expenses as a cost of doing business. I see payroll, marketing, and technology as investments and measure them by ROI. Hire someone at a million dollars a year, then figure out how to make five million from that investment.
Why did you and your son Levi start Casper, and how do you split the work?
I have relationships across many industries and I think in problems and solutions. Levi is a programmer who turns that into what the tool must do. I test by using it and point out human gaps. Our CRM pre-populates data all day so I only review it at night.
How do you get owners who say they are too busy to fix the thing making them busy?
I get to know the human behind the scorecard first. Entrepreneurs feel they must be good at everything, but we need to understand what someone will not do and bridge that with AI, outsourcing, or insourcing. Then we build KPI-driven financials tied to their real goals.
What should never be automated?
Relationships. Human nuance matters. My CRM tool helps me remember details like that you have a two-year-old son, so I can ask about him before we start. It reminds me, but the caring and connection have to stay human.
How did your first customers find you?
Through existing relationships and discovery. When I started the accounting firm, I held six coffee conversations, told people exactly what I was building, and asked for feedback. I ended with five new clients. Casper worked the same way: ask where they spend too much time, build a tool overnight, and they become clients.
What one AI tool should an owner set up this week?
An email recap. I get one at 7 a.m. for yesterday and one at noon for the morning. It reads but cannot send email, classifies what is urgent, and lists outstanding action items. It works like an EA or VA and consolidates my follow-ups.
What do you wish every owner knew on day one?
Humans run companies, and numbers are only as good as the action you take on them. Know what you are willing and not willing to do so you have reasonable expectations. Do not waste time reading financial statements if you will not act on them.
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