For founder-led companies between $1M and $5M
Growing the company is one of four things that decide what you actually walk away with. I have personally done all four — built software companies, sold them, and kept what came out the other side.
Somewhere between one and five million, most founder-led companies stop growing for the same reasons — and almost none of them are the reasons the owner is worried about.
The product works. Customers stay. The team is decent. And the revenue line has been flat for three years while the owner works harder than ever. That is not a product problem or a market problem. It is a structural one, and it is fixable.
Every advisor sells the first one. What decides what you keep is the other three.
The weekly work: operating cadence, org design, sales capacity, conversion economics, and where the next dollar goes. The part I do best inside this is go-to-market design and getting the product aligned behind it — who you sell to, what the offer is, and what makes a buyer move now instead of next quarter. Most companies your size have a good product and a go-to-market that grew by accident around it.
Every advisor sells this stage. Few can do the go-to-market piece.Structure decides how much of the value you built actually reaches you. I run a tax planning software company used by CPAs and tax strategists nationwide, and I bring that network to the entity structure of the business and the tax position of the owner — well before a sale, not during one.
On an eight-figure exit, frequently worth more than the advisory fee itself.The metrics a buyer scrutinizes, the narrative, the diligence file, the concentration and retention questions that move multiples. That work starts twelve to eighteen months before a process does, not when the first offer arrives. Run it like you will own it forever; build it to be sold.
I have sat on the seller's side of the table. Most advisors at this size have not.The exit is the beginning of the next problem. I teach the principles behind my own systems to owners who want their capital working on a defined, repeatable basis rather than parked — and introduce the licensed professionals who implement. Education and frameworks, not investment advice.
Nobody else in this lane offers it.Every area of a company, and every leader running one, can be evaluated through three questions in sequence. The useful part is not the three words. It is that each level of failure points somewhere different.
First: are the right things even defined here?
Is there a sales process that has actually produced results? Do you know the three to five things only you should be doing? Nothing below can be scored until that is answered — and more often than not, the answer is the finding.
Are the right things being done — even when nobody wants to do them?
Are they being done week in and week out, without fail? Anyone can be disciplined for a day. Consistency is discipline surviving a busy month.
When the area hits a plateau, is there the will to confront it and change what has to change? Even a disciplined, consistent team eventually hits a wall.
Most advice stops at the team is not executing. This keeps going until it can say whose problem it is and what kind — which is the difference between a diagnosis and an opinion. You will always know which one I think it is, and why.
One day on site. Six to eight hours, a whiteboard, and your business taken apart and rebuilt in front of you.
$10,000Credited in full against the first month if we go on to work together
We go top to bottom: revenue engine, unit economics, people and bottlenecks, product and position. I build your funnel math on the board in your own numbers. Then we name the one constraint holding the business at its current size, put a monthly cost against it, and build the ninety-day plan together before I leave.
You send pre-work ten days ahead so we spend the day fixing things rather than establishing facts.
Ask about a dateWhether or not we work together afterwards, the plan is yours.
The Strategy Day is not a sales call with a fee attached. It is mutual diligence.
By the end of it I have spent eight hours inside your numbers, your team and your thinking, and you have watched exactly how I work. That is enough for both of us to know.
If I offer to keep going, it is because I believe we can produce a real result together — not because there is a slot open. I take three clients at a time, I have turned down companies I genuinely liked, and being told no at the end of the day is a far better outcome for you than twelve months of the wrong fit.
Either way the plan is yours, and I will tell you honestly what I would do next if it is not with me.
A plan is not the hard part. Executing it for twelve months while running the company is the hard part. That is what the ongoing partnership is for: ninety minutes with me every week, working your plan, plus a bench of specialists to plug in where the plan calls for them.
A flat monthly fee, twelve-month minimum. Simple, predictable, nothing to calculate. For owners who want the work and want the cost known.
A reduced monthly fee plus a share of the gross profit growth above a baseline we fix on day one. Lower fixed cost to you, and my incentive pointed at the same number as yours every week.
Both include a share of the transaction value if and when the business sells — so every recommendation from day one is aimed at the number on the other side of a sale. Terms are discussed at the end of the Strategy Day, once we both know what the work actually is.
Some of this is me. Some of it is a specialist I bring in and manage against the plan. You should know which is which before you hire anyone, so here it is plainly. Specialists contract with you directly at their own rates.
Other functions — fractional CFO, recruiting, specialist legal — are sourced and vetted from my network as the plan calls for them. Any referral arrangement I have with a provider is disclosed to you in writing before you engage them.
Entrepreneur and investor. Twenty-five years building companies, and twenty of those also teaching people how to build wealth.
I started my first business out of college and failed at it. I could sell. I had no idea how to run a company, lead people or build a team. Everything I do now comes out of learning that the hard way.
Since then I have been part of six companies through to an exit — two I founded, the rest I joined and helped build. My companies have made the Inc. 5000 six times, seven counting the Entrepreneur 360. Grasp Technologies, a data and intelligence platform in the travel industry, was one. My current operating company, TaxPlanIQ, is another: we have grown it more than tenfold in two years, and it ranked #644 on the Inc. 5000 and #50 in financial services.
Alongside the software companies I have spent two decades in financial education, and I still run those businesses today — 12 Minute Trading, the WealthStacker System, and GainStacker, a rules-based signal platform running a 95.6% win rate that returned 100% of capital in under seventeen months. I include them for one reason: they are the clearest proof I know how to design a system that actually produces, and then get people to run it.
I host The Misfit Entrepreneur, a top-25 entrepreneurship podcast with more than 460 episodes and listeners in over 100 countries, and I wrote The Ten Year Career and Rage and Reason. Away from work I am a multi-time Ironman World Championship qualifier. Qualifying is a systems and execution problem far more than an athletic one — discipline over motivation, standards that do not bend — which is the same thing I am hired to install in a business.
Tell me where the business is and what has stopped moving. If it is a fit, we will find a date. If it is not, I will tell you that and point you somewhere better.