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Dickson Wasake has worked from Uganda to the Bahamas, the UK, Canada and now Illinois, with stops at PwC, Baker Tilly and Deloitte's national office. Today he runs Jedidiah CPA, and he says plainly that he can't do his work without a bookkeeper on the team. In this conversation he tells bookkeepers what a CPA looks for, what raises a red flag, and how to build the kind of partnership that brings referrals your way.
When private equity bought his large CPA firm, Dickson had 10 days to decide whether to stay on in a changed role or go out on his own. He calls it "extremely, extremely tough," especially as a family man, but three-plus years later his reaction is "why didn't I do this earlier?" What he values most is the freedom and the diversity of cash flows. He also has a message for solo bookkeepers who doubt themselves: "Someone will always need bookkeeping support. There is no job I do without needing a bookkeeper."
Getting the basics right, meaning regular reconciliations and clean bookkeeping, is the starting point. What sets the best bookkeepers apart is being proactive: flagging items early and doing what they said they'd do. If they can't get back to him today, they say so, and then they follow up on the day they promised. Dickson also names the opposite behaviors that signal trouble:
Michael adds that communication is a small-business survival skill, and that a system for tracking incoming messages beats good intentions.
Dickson has never had friction over who does what. He knows his own strength is helping clients make unstructured decisions, and he needs a bookkeeper to tell him what has happened in the numbers. He shares the story of a bookkeeping firm owner who wrote a memo laying out a messy audit client's problems, and who became his first call whenever another client needed a bookkeeper. On building the confidence to speak up, he compares it to a good marriage: find someone you trust, "that even when you get it wrong, they lift you up and not tear you down."
Drawing on his Deloitte quality review work, Dickson calls audit readiness "a mindset": could someone understand your work without you there to explain it? In practice that means supporting documents uploaded for entries, a monthly close, and thinking about controls over payments, system access and adjustments. He also shares a "secret": when books are messy, the fastest fix is the balance sheet, because a balance is a matter of fact. He also separates reconciled from decision ready. A bank rec can tie out perfectly while the client sits in overdraft month after month, and "a balance sheet can balance and still be fundamentally wrong."
With a bookkeeper he hasn't worked with, Dickson treats it like a job interview and listens to the questions they ask. Asking how a client likes to be contacted, whether by WhatsApp, phone or email, tells him he may have someone to refer business to. After that, it comes down to routine: reply to messages and don't ghost. If the first one or two months go well, he says, you can have a long-term relationship.
Dickson Wasake is a partner at Jedidiah CPA PLLC, based in Illinois about an hour from downtown Chicago. He began his career at PwC in Uganda, became an audit partner at Baker Tilly in the UK after 13 years, and later served in Deloitte's national office in Canada, where he worked on audit risk and quality. He now advises small business clients and works closely with bookkeeping firms.
Michael Palmer
Michael Palmer is the host of The Successful Bookkeeper podcast — almost 600 episodes and counting — and founder of The Successful Bookkeeper Global. He's spent over 15 years in the bookkeeping industry, working one-on-one with thousands of bookkeepers across the globe. He started this work because of his father — a brilliant electrical contractor who worked twice as hard as he should have had to, because nobody on the financial side was in his corner. That gap is what The Successful Bookkeeper exists to close. His view: bookkeepers are the most undervalued force in small business — and every bookkeeper who builds a real business changes two families: theirs, and their clients'.