Exit planning
Review Your Business Like an Investor Every Month
Saul Cohen explains why busy, profitable owners stay stuck as operators, and how a monthly review built on an investor's questions changes both the business and the owner.
Ep 243: From Operator To Investor
Episode from The Wealth Vibe Show.
Generated from the canonical interview transcript and validated against source data by Guests on Air.
How can a business owner start thinking like an investor?
Start by reviewing your own company the way an investor would. Saul Cohen suggests taking a day out of the office each month to ask what went well, what struggled, what must change and how the finances performed, then acting on the answers. Twelve honest reviews a year compound, and the investor identity follows the habit.
Saul Cohen, founder of The Expert Eye, began his career at PwC and now advises business owners on acquisitions, financial strategy and tax planning. Speaking with Vinki Loomba on The Wealth Vibe Show, he explained why so many successful founders stay stuck as operators, and the simple monthly habit that helped him start thinking and acting like an investor.
The warning signs are easy to miss because the business looks healthy. The owner is very busy, has hit a plateau and earns good money, yet cannot say what the company is worth, which assets matter most or what really drives its value. Cohen describes these owners as very clear on profit and loss but much less clear on value.
His answer is not a new strategy or a bigger target. It is a routine of stopping, measuring and reviewing, done every month with the questions an outside investor would ask. Over time that routine changes how the owner sees the business and, just as importantly, how the owner sees themselves.
Key takeaways
- Owners who cannot say what their business is worth, or what drives that value, are still thinking like operators.
- Stop, measure and review every month, which gives you twelve chances a year to improve instead of repeating the same year.
- Take a day out of the office and question your business the way an outside investor would.
- Ask for help early, because a coach or adviser can show you what you cannot see from inside.
1. Avoid living the same year twenty times
Cohen's biggest fear in business was a simple one. An owner can gain twenty years of experience, or repeat the same year twenty times, and from the outside the two can look alike. He wanted to understand what separated them, and the answer he reached was to stop, measure, review and improve, again and again.
Early on he hired a business coach, partly because he knew he was struggling. The coach held up a mirror to his performance and made reflection a habit. Cohen now argues that being able to record data, stop and review how you have been doing is one of the key things anyone has to do as an investor.
The habit works because it compounds. Stopping every month to ask what worked well, what did not and what needs to change gives an owner twelve cycles of improvement a year. Each small correction builds on the last, so a year of honest reviews moves a business much further than a year spent with its head down.
2. Ask the questions an investor would ask
When an owner asks how to start thinking like an investor tomorrow, Cohen's first practical step is to take a day out of the office. Simply calling yourself an investor rarely feels real, he said, because you are not yet doing the things investors do. Doing those things first is what makes the new title feel natural.
So he asked himself what an investor in his own company would want to know. What did we do well last month, and what did we struggle with? What do we need to change or do more of? What are our strengths and weaknesses, and what opportunities and threats does the market hold right now?
He added two more: how the finances performed, and who in the business is doing well or not so well. Measuring the company against that list each month is what made him start to feel like an investor. It also gives the owner a clear view of value, not just of revenue and profit.
3. Change the identity, then ask for help
Cohen believes the founders who make the move from operator to investor share two traits. They have the humility to see their limits, review their own performance and ask for help. They are also willing to do the slow work of changing their identity, from business owner to someone who looks at companies as an investor.
He called changing your identity one of the hardest things a person can do, and stressed that it is a different kind of work from simply grinding harder. Entrepreneurs are optimistic by nature and tend to think they are good at everything, which is exactly why they so often miss what they do not know.
That is where advisers come in. Cohen compares business to a high performance sport: owners need a coach, rest, recovery and hard training, just as athletes do. Having people around who can educate and support you, in finance, HR or anywhere else, lets you put up your hand and ask for help before a gap becomes costly.
