News

Two Years of Trust: From Fed Examiner to Solo Bookkeeper

Fifteen years examining bank balance sheets and a wine shop of my own. Two years in, here's what that combination means for the businesses I serve.

Illustration of an open book reading Building Trust and A Bookkeeping Journey, surrounded by growth charts, stacks of coins, a calculator and an abacus, with a path winding toward a distant city skyline.

Two years of doing this myself

Cilson Bookkeeping turned two this year. For both of those years the business has been one person: me. I do the books, I answer the questions, and I am the one who notices when a number looks wrong. No team, no account manager, no handoff.

Staying solo is deliberate, and two years in I would make the same choice again. I work with established professional-service businesses, from law practices and agencies to design and engineering firms, SaaS companies and real estate brokerages. Their owners make real decisions from their numbers. They need to know who is behind those numbers, and they should never have to explain their business twice.

USA Today and StreetInsider (opens in a new tab) both carried my second-year announcement in their press release sections. This article is the longer version: what I bring to your books, where it comes from, and how the work runs.

What examining books taught me

I spent fifteen years as a Federal Reserve bank examiner, and my title at the Federal Reserve Bank of Minneapolis was Senior Examiner. The job was opening a set of books, finding what was wrong, and working out why it happened.

As a Federal Reserve examiner trained in commercial credit, I reviewed the financials of hundreds of businesses across most bankable industries. The question that matters is always the same: can these numbers be trusted?

That question is harder than it sounds. A set of books can look maintained and prove nothing. Transactions come in through the feed and get categorized, but that is sorting, not verifying. Until the accounts are checked against a statement, the numbers are only claims.

The problems I find most often are the quiet ones:

  • Bank and card accounts that were never reconciled
  • A personal account connected to the bank feed
  • An S corp election or entity change the chart of accounts never followed
  • A setup built for a smaller version of the business and never revisited

Balances that do not tie usually have a reason. I trace it to where it started rather than forcing the number, so the same problem is not back in six months.

My career also includes senior financial analyst roles at Target Corp and U.S. Bank, building financial models the operating units relied on. Examining taught me to find what is wrong in a set of books. Building models taught me what a business needs from them once they are right.

What owning a business taught me

For four years I also owned a boutique wine store, WineStyles of Woodbury. I juggled inventory, payroll, and marketing, with my own money on the line.

Retail teaches cash timing fast. The money left on a schedule and arrived when it felt like it. Inventory tied up cash before it earned anything, and payroll came due whether the month had been good or not.

When the business is yours, the books stop being an exercise. They answer questions you have to act on: whether you can afford to hire, whether a price is too low, whether cash will cover the coming payroll.

That is why I give clients a straight answer when they ask a question, and why I say what a number means for the decision in front of them rather than sending a report and leaving them to decode it. Four years as a business owner, like you.

How I work now

Most clients start with monthly bookkeeping. It runs month to month, in writing, with no long-term commitment, and every month closes the same way, with the books finalized in QuickBooks® Online.

If the books are behind, or the file itself needs repair, catch-up and cleanup comes first. Setup and migration covers a new file or a move from another system. Job costing and advisory services, including cash flow forecasting, are there when a business needs them.

Every client gets their own secure portal. Source documents go there, I publish monthly financial reports there, and routine messages run through it, so nothing important ends up buried in an email thread. I reply within one business day, if not sooner. A financial review by video or phone is available every month, and clients decide when they want one.

What to ask any bookkeeper

Whether or not you ever work with me, these are the questions worth asking before you hand over your books:

  • Who will actually do the work, and will it be the same person every month?
  • When is each month closed, and when will you see reports?
  • When a transaction is unclear, will they ask you or guess?
  • Is every bank and card account reconciled to its statement each month?
  • What is included in the price, and what gets quoted separately?

If the answers are vague, the books usually are too. For how pricing usually works, see my guide to bookkeeping pricing, and for the monthly work itself, what monthly bookkeeping really includes.

If you'd like to talk

It starts with a free 20-minute call by phone. You tell me where things stand, I tell you whether I can help, and there is no obligation on either side.

If I can, a books health check follows. I review what you have, walk you through what I found, and that is where you get a recommended scope and a firm price.

Explore bookkeeping services

Christopher Wilson

Expertly led

Hi, I'm Christopher Wilson: Your one-on-one partner in profits, time, and peace of mind. I turned 20+ years of finance, audit, and hands-on ownership into one promise. I'll treat your books with the same care I once gave billion-dollar balance sheets. Only now my focus is on you.

Fast facts & credentials

  • Certified QuickBooks ProAdvisor: I keep up so you don't have to.
  • BBA in Finance, Investment and Banking, University of Wisconsin–Madison.
  • Two-time business owner: retail wine shop and now Cilson Bookkeeping.
  • Serve nationwide from my home base in Littleton, CO: 100% remote, 100% personal.

Want a second opinion on your books?

Tell me where things stand and I will tell you whether it is a quick fix, a real cleanup, or nothing to worry about. You would be working with me directly, start to finish.

Book a free 20-minute call

Twenty minutes, and you can stop working it out on your own.

Rather send a message?