Gregg: No More Flying Blind

He runs his own finances on Profit First: pay yourself a set owner’s draw, set money aside for taxes, and never get blindsided in April. He uses Cashflowy to do it, which is exactly why his take carries weight.

Ask Gregg what happens when an agent skips their bookkeeping and he doesn’t start with April. He starts with the other eleven months.

“I’ve worked with and spoken to so many agents who were behind on their books because it felt overwhelming. January becomes March. March becomes July. Before they know it, tax season arrives, and they’ve created a nightmare project for themselves. It creates stress that’s completely avoidable.”

And the damage isn’t only stress. Every decision an agent makes without clean numbers is a decision made on a guess.

“You can’t make good business decisions without good information. If you don’t know what you’re actually making, what your expenses are, or what you can safely pay yourself, you’re guessing. And successful businesses can’t be run on guesses.”

Gregg’s theory of why agents fall behind is refreshingly simple: bookkeeping is a chore, and people avoid chores. The answer isn’t more discipline, it’s removing the friction so keeping up stops feeling like work in the first place.

“I like Cashflowy because it removes friction. Agents avoid bookkeeping because it feels tedious, confusing, and time-consuming. Cashflowy automates so much of the categorizing that staying on top of your finances becomes exponentially easier. And when something is easier, you’re much more likely to actually do it consistently. It also takes a huge amount of the dread out of tax season.”

Two months in, he can already feel how little the work asks of him now.

“I’ve only been using Cashflowy for about two months, but it’s already made staying on top of my books dramatically easier. It’s smart enough that it categorizes most transactions automatically, so there’s far less manual work.”

The clearest proof came early, with a part of his finances that had always been a headache. Under Profit First, Gregg pays himself an owner’s draw and then moves money into a separate tax account, transfers between his own accounts that his old software, Wave, could never make sense of.

“When I pay myself an owner’s draw, I’m transferring from one account to another, and then taking money from that same account and putting it to a tax account. Wave would have such a difficult time understanding what all of those transactions were, and it became a mess.”

Cashflowy recognized it on its own and tied the two sides together as a match transfer. The reaction was immediate, and unscriptable.

“Cashflowy immediately recognized that and called it a match transfer. So I was just super grateful that problem was solved, because it was a nightmare in Wave. And when I saw that, I was like, "God bless you"”

What keeps that confidence going is knowing the software isn’t the only thing behind him.

“The other thing I really value is knowing there’s a human bookkeeper I can reach out to if I have a question. That combination of smart software and actual human support gives me a lot of peace of mind.”

Gregg isn’t guessing whether this works for agents. He lived the before, he uses the after every day, and he coaches the exact people it’s built for. When the person agents turn to for advice on running their business picks a tool, you should listen.

Gregg’s case for Cashflowy is the case he makes to his own clients. Bookkeeping doesn’t get done because it feels hard, so the answer is to make it easy: automate the categorizing, keep a real human within reach, and turn a year of flying blind into numbers you can actually see. Two months in, the dread is gone and the guessing is over. That’s the difference he wants every agent he coaches to feel.