Caylee Robles: How to Pay Yourself Consistently on Sporadic Real Estate Income

Caylee Robles is a retired CPA turned Florida real estate agent who spent five years earning her accounting credentials at the University of Wisconsin before walking away from Deloitte to chase real estate. After six months without a paycheck, a $90,000 wholesaling run, and two years of raiding her own tax account, she built a Profit First system that now pays her a salary every 1st and 15th and could carry her through six months of zero income.David Richter and Caylee dig into why agents stay trapped in feast or famine, why she deliberately chose the lower risk agent path over investing, and the exact account structure that let her double three years of income in a single year. If you're a real estate agent or investor whose commissions land straight in your personal checking account, this episode is your wake-up call.Timeline Summary[0:33] – David sets up the episode: thinking like a business owner and building systems that keep more of your money[1:15] – Caylee shares her backstory: decided at age eight to become an accountant, earned her CPA at the University of Wisconsin[2:39] – Within a month at her first accounting job she knew she hated it, searching real estate jobs every night during busy season[3:43] – Where her "do hard things" wiring came from: two parents in sales who worked 25 years before the payoff[6:07] – The three year transition out of accounting: Deloitte auditing, a real estate internship, and an Austin transfer that closed the door[7:42] – Underwriting $1 million plus luxury leased homes across the Caribbean, Mexico, and South Florida[8:08] – Joining New Western at the end of 2022: "you eat what you kill," 75 to 80 hour weeks, and two months with no income[9:39] – Six months without making a dollar, then $90,000 in three months wholesaling with her partner[10:10] – Setting up her LLC and Profit First accounts on Relay before the money ever showed up[11:49] – The two year struggle: pulling from her tax account to pay personal credit cards during the lean stretch[13:38] – The 2025 turning point: repeat client business and splits big enough that she never touches her owner's distribution account[16:38] – Her S corp structure: salary every 1st and 15th, SEP IRA contributions, and distributions on top[17:19] – In 2025 she doubled what she made in the three prior years combined, and 2026 has already matched it[21:25] – Why agent risk beats investor risk: her downside is time, while investors she works with have $300,000 on the line[23:21] – Diversifying beyond real estate: 401k, SEP IRA, joint investments, and a 3% interest rate home that becomes a rental[29:59] – Her one move to make this week: set it up as a business with an LLC and dedicated business accounts5 Key TakeawaysTreat Yourself Like a Business Owner — Whether you're an agent or an investor, you're self-employed, and that means acting like it. An LLC, a business checking account, and dedicated tax and owner's pay accounts come before anything else.Set Up the System Before the Money Arrives — Caylee opened her Profit First accounts while she was broke, so when the $90K hit there was already a place for every dollar. The foundation matters more than the timing.Risk Your Time, Not Your Money — She left investing for the agent side on purpose. A canceled listing costs her hours, while an overleveraged flip can cost an investor six figures at inspection.Automation Removes the Willpower Problem — Money hits her Relay account and splits instantly: credit cards paid, SEP IRA funded, salary scheduled. She only touches the system when she overspends.A Buffer Buys You the Power of No — With six months of runway in the business, a slow summer doesn't create panic. Financial cushion is what turns "what do I need to do" into "what do I want to do next."Links & ResourcesSimple CFO — https://simplecfo.comFollow Caylee Robles on Instagram — https://instagram.com/thedailycayleeRelay business banking — https://relayfi.comProfit First by Mike MichalowiczEnjoyed This Episode?If Caylee's story of going from raiding her tax account to a self-paying salary every two weeks hit close to home, don't keep it to yourself. Share this episode with an agent or investor whose commissions are still landing in their personal checking account. Then follow the show and leave a rating and review so more real estate professionals can find Profit First.