Journey From CFO to Lawyer: Why I Became a CPA Attorney
For many years I was a Controller, and then a CFO of various businesses in several industries. That journey – from the accounting department to the boardroom to the courtroom – is why clients hire me today as both a CPA and an attorney.
At first, like many Controllers in small to mid-sized businesses, I did everything. Financial reporting and budgeting, yes, but also HR functions, handling various tax issues, managing cash flow, negotiating with vendors, and cleaning up books that hadn’t been closed properly in months.
As I got more experience, the role expanded from accounting to strategy.
From Controller to CFO: Building Companies, Not Just Closing Books
The transition from Controller to CFO happened when I stopped just reporting history and started planning the future. I became involved in multiple M&A transactions and worked directly with founding teams to build several companies from early stage to exit.
That work included raising $35 million in debt and equity financing, serving as a Public Company Board Member for 5 companies in multiple countries, handling SEC reporting including 10-K, 10-Q and 8-K filings, leading 5 IPOs and DPOs from audit prep to S-1 and offering documents, and planning for growth, supervising staff, and advising on strategic issues.
When you have been the CFO who has to explain a missed forecast to a board, you look at legal documents differently. A contract isn’t just legal language – it’s a financial model, a risk allocation, and a future audit issue.
Two Certifications That Changed My Career: CVA and CFE
After several acquisitions, I kept running into the same problem: how do you value a private business fairly? So I became a Certified Valuation Analyst (CVA). Since then I have performed over 50 business valuations for 409A valuations, purchase price allocations (ASC 805), shareholder disputes, marital dissolutions, and buy-sell agreements.
The second certification came from a harder experience. I uncovered an embezzlement inside one of the companies I was advising. Following the money, documenting the scheme, working with counsel – that was forensic accounting in real time. After that case, I became a Certified Fraud Examiner (CFE).
From Finance Expert to Expert Witness to Law School
Around the same time, I started seeing litigation surrounding usurious lending, complex debt structures, and breach of contract cases where attorneys and judges were struggling with the financial issues. Damages needed to be calculated.
I decided I could use my financial experience to become an expert witness. I began consulting on financing, reorganizations, shareholder disputes, and damage calculations.
Doing expert witness work, I was in court, in depositions, and in strategy meetings with litigators. I decided to go to law school. Eventually I passed the Bar exam and became a lawyer – CPA, Esq., CVA, CFE.
Why a CFO Background Makes a Better Business Attorney
There are a lot of good business lawyers. There are very few who have closed the books, raised the money, sat in the board meeting, and testified about the damages.
1. Securities and Fundraising:
I Have Sat On Your Side of the Table
I handle securities opinion letters, input into private placements and offering documents for Reg D, Reg A+, and DPOs. When I draft them, I am thinking about what the SEC will ask and what your future auditor will say.
2. Contracts and M&A: I Read Them Like a CFO
A purchase agreement is not just reps and warranties. It is working capital adjustments, earnout accounting, and tax allocation. I handle contract review, negotiations, and buying or selling a business.
3. Litigation Strategy and Expert Witness Support
I still provide expert witness services for damage calculations. Now as an attorney, I also handle discovery preparation, litigation strategy, and dispute resolution with an understanding of how a financial expert will calculate damages.
4. Employment, Bankruptcy, and Practical Business Advice
As a CFO I handled HR functions, so I understand employment hearings operationally. In bankruptcy preparation, I can build the 13-week cash flow model that the filing requires.
Legal Services I Offer With a CFO Lens
- Demand Letters and Cease & Desist Letters
- Securities Opinion Letters and Offering Document Review
- Contract Review and Business Negotiations
- Business Valuations and 409A Valuations
- Expert Witness Services – Economic Damages and Financial Forensics
- Employment Hearings and HR-Related Disputes
- Discovery Preparation and Litigation Strategy
- Bankruptcy Preparation and Reorganization Support
- Dispute Resolution and Shareholder Disputes
The Bottom Line
I did not go from CFO to lawyer because I was tired of finance. I went because I saw too many business disputes where the lawyers did not understand the numbers and the accountants did not understand the law. The most expensive mistakes happen in that gap.
Contact me through hpaccounting.com/contact.