Why are you doing this?
I’m doing this because I want to build long-term ownership in one great, durable business, and I want to do it the right way. I’ve spent the last decade building and operating service businesses. I raised outside capital, acquired a company, and ran it as CEO. That experience made something very clear: I want to spend the rest of my career leading and growing the small businesses that have made America what it is today.
Why are you using this approach instead of buying a business outright?
Because it’s safer. For you, for me, and for your employees.
We get time to know each other and build trust before anything is permanent.
You get a real view of how I operate, how I treat people, how I make decisions, how I handle challenges.
Employees get a gradual transition, not a sudden leadership change that creates uncertainty.
The business gets time to become more transferable, which helps you whether I buy it or you ultimately sell to someone else.
I am going to live and raise my family in Chicago, and it is important to me to treat employees, customers, and the community as a part of that family. That means taking a thoughtful approach.
If we moved forward, how would this work?
Phase 1: 90-day contract trial
I join on a contract basis for 90 days. During that period we:
- confirm we work well together,
- Identify the highest-impact priorities
- Complete at least one meaningful project that improves the business.
At the end of the 90 days, we decide together whether to move forward.
Phase 2: Full-time leadership (1–3 years)
If the fit is strong, I join full-time and we transition me into a General Manager/President role. Over 1–3 years, my job is to:
- reduce owner-dependence,
- professionalize systems
- strengthen the management team,
- improve growth and profitability
- prepare the business for a clean transition
Phase 3: Purchase or market sale
At the end of that period:
Option A: I make an offer to acquire the business and operate it long-term.
Option B: If it’s not the right fit for me to buy or If you prefer to sell to a third party, I help you prepare and run a strong sale process so you can achieve the best outcome.
Are you only looking in Chicago, or would you move to where the business is?
I’m committed to living in Chicago long-term. I moved back to build my life and raise a family here.
That said, I’m open to businesses across the broader region, including:
- Chicagoland
- Southern Wisconsin
- Northern Indiana
- Central Illinois
I can travel as needed, but I’m building this in and around Chicago.
What makes you qualified to run my business if you haven’t run this exact type of business before?
You’re right to ask that, and it’s one reason I use a gradual approach.
I may not have run your exact business, but I do have deep experience in the things that make service businesses succeed:
- Building and managing teams,
- Creating accountability through metrics and cadence,
- Strengthening sales process and customer retention
- Developing partnership channels
- Improving operational clarity
- Making a business more transferable and less dependent on the owner.
The 90-day trial and the 1–3 year transition period aren’t just polite, they’re practical. They give me time to learn your specific industry nuances and earn trust with your team and customers.
What does success look like in the first 90 days? In the first year?
Success in the first 90 days
- Fit: We both feel confident that this is a strong match culturally and professionally.
- Value: I’ve completed at least one major project that tangibly improves the business (examples: sales pipeline clarity, pricing/offer cleanup, reporting systems, customer retention work, operational bottleneck removal).
Success in the first year
Success in year one looks like:
We have a shared 12–24 month plan with measurable goals toward a transition
I’m fully operating as GM/President
You’ve meaningfully reduced your day-to-day workload (you have real time back)
The team is clear on roles, priorities, and cadence
Key reporting and operating rhythms are in place
What happens if either of us decides this is not the right fit?
If we decide during the 90-day trial that it’s not a fit, we simply wrap up professionally. You keep the improvements we made, and we part on good terms.
If we’re further along and you still want to sell I can help take the business to market or I can connect you to the right advisors to run a strong process to get you top dollar for your firm.
If you decide you don’t want to sell anymore, we can structure an amicable exit that respects the work done and the equity terms we agreed to.
Are you promising you will buy my business in 1-3 years? What if you cannot get financing?
My intention is to buy the business. I already have a track record of successfully completing acquisitions in the $10M–$20M valuation range, and I have the relationships with the equity investors and lenders needed to close confidently.
Here’s what I can commit to:
- We will define a clear purchase path early (timeline, valuation framework, and structure).
- Your team, your customers, and your legacy will be cared for at every stage of the process.
- I will communicate transparently throughout our time together and put forward a fair offer we are both excited about.
What systems /processes will you want to implement and how disruptive will that be?
It depends on what the business truly needs, and we’ll do it in a way that protects what already works.
My approach is:
- Start with the least disruptive, highest leverage changes
- Build systems that make life easier for the team
- Implement changes in phases so the business continues to run smoothly
Common areas I’ll often improve:
Basic SOPs for repeatable delivery
Weekly operating cadence and simple KPI reporting
Sales pipeline and lead follow-up discipline
Customer retention processes
Conversion to G.A.A.P. accounting
Financial visibility and forecasting
Process automation and systems integration
Who is in charge and how do employees experience the transition?
During the 90-day trial, I’m there to learn, contribute, and execute on agreed projects; you remain the owner and final decision-maker.
As we move into the GM/President role, the goal is a clear and respectful leadership transition:
- Employees get clarity on who owns what decisions,
- The owner isn’t undermined,
- The team sees stability instead of uncertainty.
Practically, that means:
- We agree on which decisions are “mine,” “yours,” and “shared.”
- We communicate the transition to employees in a way that builds trust and protects morale.
- Over time, you step back from day-to-day operations while staying informed.
How is a purchase price determined if you do buy?
A purchase price is typically determined by:
- comparable transactions in the market (what similar businesses sell for),
- the quality of earnings and customer stability,
- the strength of the team and transferability,
- growth prospects,
- and the risk profile of the business.
My philosophy is simple: I’d rather buy a great business at a fair price than a fair business at a great price.
If the business is strong and we build trust over time, it’s in my interest to pay a price that feels fair and respects what you’ve built because I want a strong business to run over the long term.
What is my downside if this doesn’t work out?
The downside is intentionally limited; it’s a core benefit of this approach.
There are multiple “off-ramps” built in:
- The 90-day trial is a defined window to test fit.
- You’re not committing to a sale on Day 1.
- If we proceed further, we document expectations, authority, and equity clearly so nobody is surprised.
Even if we don’t end up doing a purchase, you still benefit from:
- A more professionalized business
- Stronger systems and reporting
- Growth improvements
- A business that is more transferable and attractive to buyers.
The whole structure is designed so that you’re better off even if the end outcome changes.