What Is a Business Strategist for Self-Funded Founders?
A business strategist for self-funded founders helps owner-operators who are not seeking venture capital build profitable, sustainable, values-aligned companies. Unlike single-lane advisors (finance, legal, operations), a generalist strategist holds the whole picture — from revenue model to team structure to growth path — and stays in the work alongside the founder.
“Jill, what exactly is it that you do?”
At some point, life evolves from being asked “What do you want to be when you grow up” — astronaut pizza chef veterinarian, of course — to “So, what do you do?”
The people who want to hire you need to know if you’re for them, and you need to know if you even want to take the work…myself included.
So, like you, I get asked this question a lot. The problem is, my answer is a little complicated.
In one camp, we have Billboard People. These are people who can say what they do in a pithy little statement or with an acronym, because they do a thing you already understand or solve a well-established problem. And there are Podcast People, who need some space for nuance and relationship-building.
I am a Podcast Person. But I don’t have one of those, so this newsletter will have to do.
It’s easier to start with who I’m for, because the job-title version gets murky fast. My clients often use shorthand, like “she’s my CFO,” because there isn’t a tidy word for our work situationship. We all need to use numbers. We all need to work through growth and feelings. Neither of those things box me into CFO or “business therapy.”
So, we’ll start with the who:
I help self-funded founders who want to build profitable, sustainable, values-aligned companies.
When I say “self-funded,” I’m not saying you can’t be someone who’s never taken out a loan or had a business partner. All it means is you’re not going out to raise money. If you’re not seeking venture funding, we’re good.
If you have a distinct opinion of how you want to make the world a better place with your work, then we’re even better.
I work with my clients in 2 ways
1) Strategy engagement (finite)
This is for people who have started something, but they’re feeling stuck. They can’t find the path to where they want to go without losing their why.
They know they’ve got a good business in front of them, but it’s not working for them right now. There are too many decisions. They know what they need to get paid and what they don’t want to do, but they can’t turn that into a plan that they feel ready to act upon.
So we figure out:
What you want this business to be
What your job is in the business,
What you stand for, how you’re going to make money
What the growth path looks like for the next 18 to 24 months
We do the work over a few weeks so you have time to reflect and make sure it works for you. You walk away with direction and some clear, impactful actions toward your goals.
2) Fractional general management
Some clients want me to stay on and help implement the plan. That’s where my role gets murky, but in a good way.
Once you’re growing, hiring, setting up in another state, and dealing with compliance, legal, operations, people stuff, finance, supply chain, and nexus, small businesses get complex very fast. You need to level up, but you don’t have time or money to manage six domain experts.
That’s why I call it “fractional general management.” With our partners, we can be the team captain and your partner for managing all the financial, administrative, and probably boring-but-necessary stuff it takes to grow and run your company.
What problems I solve for clients
This is a short answer, but it encompasses a lot.
“I need to make this business work. I kind of hate it right now.”
Under that is usually:
“I know there’s a good business here, but I can’t see the path. I have too many options. I don’t know what to do next. I can’t get from my messy pile of thoughts and tasks to a meaningful plan.”
And that’s where we get to work.
Here’s what I’m not
I’m not a coach.
I know lots of great coaches, many with mental health training, which I think is important. For me, I don’t like telling people what they should do and then letting them wander off into the world to figure it out.
Many entrepreneurs use coaching as implied permission to carry out a plan that they’ve been advised against, or they confuse a coach with a therapist. That really isn’t what I do. We problem-solve, and we build things together.
And yes, people ask if there’s a way to just “get my ideas” without engaging with me so intensely. Absolutely! You’re reading it. There’s a whole free archive of eight years of my opinions about what you should do.
My best work happens when I’m integral to the function of your company, doing the hard stuff that most people want to walk away from. I moved to this freemium model because if you’re paying me, I want to be a partner in running your company.
What makes working with me different?
Usually people can give you an answer for your business from their single lane of expertise.
Finance people will protect your cash flow or balance sheet. Lawyers will consider the worst downside risks. Operators will push for norms and systems. And most everybody will cover their booties to limit their liability while earning your fees.
Now we have some pretty good AI, which, if you’re using it right, you can ask to take on these roles. For example, you prompt, “You are a CFO of an early stage company.” You will get a very good “what a CFO would say” answer. Then you ask what a COO would say, then what a CMO would say, and you end up with three different answers. Your next prompt, “Now what the f*** do I do?” isn’t going to end well.
The difference is I’ve had all of these jobs. I’ve managed a lot of companies from figuring out their first dollar to up to $25 million. And here’s what I’ll ask you:
What outcome are you trying for?
What’s important to you?
What is your risk tolerance?
How much money do you want to make?
Only you can answer these questions. One more piece: I’ve been a personal wealth manager, which means I can speak to smart ways to accomplish your goals.
It’s all about the outcomes
When I work with clients, I’m managing toward the end goal with the guard rails that you define. We’re not just talking about what you could do. We’re making decisions, getting you through the messy parts, and keeping you in the entrepreneurial game while you learn and grow.
What does that look like? It’s different for each client.
But every single client has a moment when we’re in the shit. No matter how well we plan, everybody has their crucible leadership moment.
Day-to-day cash flow. A crunchy month or quarter, when every decision and dollar spent matters. The job is sustaining the business, but also supporting you as you manage your way through. You’re the CEO. I will tell you what I think. If I say Door No. 1 and you choose Door No. 2, we’re on the ride with you. After 12 years of working with founders, I’ve learned that you can’t cheat a CEO out of the experiences they need to have. You can just be there with your whole heart, support them, and help them find their way to the other side.
So if what you want is someone to give you permission for something you were going to do no matter what, I am not your person.
But if you want a partner who can help you decide what to do, help you actually do it, and stay steady with you through the messy parts inside your business, that’s what I’m here for.
And if you’d like to set up a conversation to see if I’m the right person to work with you, I’d love to talk to you. Otherwise, I am genuinely happy you’re here as a subscriber.
