Gregg: From “Nightmare in Wave” to “God Bless You”

Gregg Sugerman is a real estate coach. He runs his own coaching business and spends his days helping Compass agents build theirs, which means he practices what he preaches about treating your business like a business. He’s honest about the gap between the dream and the day-to-day.

“It’s that, like, what people think an entrepreneur’s life is like versus what it’s really like.”

Part of running it like a business, for Gregg, is Profit First: pay yourself a set owner’s draw, move a cut into a separate account for taxes, and never get blindsided in April. The method works. The software he was using to track it didn’t.

Every draw and every tax set-aside meant money moving between Gregg’s own accounts. Wave saw two disconnected transactions instead of one movement of his money, and it had no idea how to categorize them. Multiply that by every pay cycle, and his books became something he had to untangle by hand.

“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 did the thing Gregg hadn’t thought to request. It recognized the money moving between his accounts, tied the draw and the tax transfer together, and labeled the whole thing a match transfer, on its own. No manual cleanup. No guessing. The workflow that had been a nightmare in Wave simply resolved itself.

“Cashflowy immediately recognized that and called it a match transfer. So I was just super grateful that that problem was solved, because it was a nightmare in Wave.”

The relief was instant, and so was his reaction. It’s the kind of line you can’t script.

“And when I saw that, I was just like, oh, God bless you, Heidi.”

Gregg isn’t only a happy user. He coaches real estate agents for a living, an audience of people who run exactly the kind of commission-based, pay-yourself, set-aside-for-taxes businesses that Wave and QuickBooks handle badly. When someone who teaches other business owners how to manage their money switches tools and then puts his own name behind the new one, that’s a different level of endorsement. He’s not guessing whether it works. He lived the before, and he chose the after.

Gregg’s story is the cleanest kind of before-and-after. Same person, same Profit First workflow, the same owner’s draw and tax transfers every month. In Wave, a nightmare he untangled by hand. In Cashflowy, recognized and matched automatically. For any solopreneur who pays themselves and sets money aside for taxes, that one difference is the difference between dreading your books and trusting them.

Disclosure: Gregg is also a paid affiliate and webinar partner of Cashflowy. His experience described here is his own and predates that partnership.