What I'm Doing Next

TLDR: After stepping away from the company I cofounded, taking over a year off, and doing a ton of reflection, I’m starting a new company to help professional services firms grow.

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13 years ago I started Digital Intent with my two partners. In the beginning it was a product dev shop - we were a team of startup guys who had complementary skills and thought we could increase the odds of success for our clients.

It worked - 30% of clients who worked with us successfully raised or got acquired, at which point they usually brought things in house. Great outcome.

Over time that company moved upstream to work with enterprise innovation teams. They had similar issues, similar ambitions, and more money. We got to build super cool products for companies like the Chicago Bulls, Chicago Tribune, NBC, Kindred Healthcare, etc.

Along the way we started an early stage fund, made around 25 investments in startups, had several exits. Eventually we started doing everything under one umbrella organization called Manifold. We grew fast enough to make the Inc. 5000 several times. I had the good fortune to be able to teach hundreds of MBA students digital marketing at Kellogg.

It was a wild ride. I grew in so many ways, learned a bunch of lessons, and got to work with tons of awesome people.

But as we entered 2022 and started thinking about what the next 10 years would look like for the firm, I realized I didn’t want the same things. For the first time in my life I was also struggling with some anxiety issues, which wasn't fun.

So I told my partners I wanted to step away from the business.

Taking time to reflect

The timing ended up being perfect for our family - my wife had just taken a role as Chief Revenue Officer of an investment bank, which promptly was acquired by a major private equity group and suddenly had ambitions to 10x. While she never stopped working when we had kids, I do think in many ways she let me prioritize my job ahead of hers for years. It was my turn to return the favor.

So I basically took a year off. I took on the primary responsibilities at home. I started helping her run her 500-member non-profit as a kind of behind-the-scenes COO.

I started a once a year coaching group helping people implement tools to build more intentional lives - loved it, and plan to continue doing it once a year (next cohort starts next week if you want to join us!)

In the middle of 2023 I started kicking around some ideas for new things. Using the customer development playbook, I learned one idea was awful, and another was meh.

But the third had legs. I knew I could execute on it. It was easy to explain. It got great feedback from the market. (More on that shortly.)

I learned a bunch during this time. Some of my biggest reflections:

Amazing things can happen when you think in 10 year time horizons.

When we started Digital Intent back in 2010, I had no idea what it would become. If you would have told me I wouldn’t have believed you.

It’s hard to build something amazing in a year. But I learned in 10 years you can do some awesome stuff.

I’ve started thinking in 10 year time horizons with more things, and I’ve been teaching other people to do the same.

They are more realistic. They prevent you from thinking you need to take crazy swings. They are sustainable - you can execute on them without risking burnout.

They also give you more joy. There’s research that suggests we don’t get joy from accomplishing goals (as many of you have probably discovered). You get joy from setting the goal, and then by noting your progress toward the goal. The whole journey vs. destination thing. If that’s true, then by setting 10 year goals I get to note progress for 10 years. More joy.

Beware conflating your job with your life.

I used to tell founders all the time to be careful aligning their identity too closely to their company. Either it will fail and they’ll conflate that with “I’m a failure”, or they’ll succeed, exit, and not know what to do with themselves.

I thought I wouldn’t have that issue since I was aware of it. But I was wrong.

When you invest in startups, people want to talk to you - all the time. They want to know how you managed to get the gig in the first place. They want to tell you about their idea. They want to see if you would write them a check.

I love talking to people, love kicking around ideas, love trying to be as helpful as I can.

And if I’m honest I liked feeling “important.” Feeling “unimportant” took some getting used to. I worried about what I’d say at a dinner party when people asked me what I did. I worried what they’d think (turns out they aren’t thinking much about me at all.)

The power of disciplines.

One help for me during this time was the cultivation of solitude as a discipline. A mentor once told me a discipline is "anything that helps you do what you cannot do by direct effort."

With solitude, I would retreat (sometimes to a quiet place in my house, sometimes to a cabin in the woods). I wouldn’t take my phone, or a book, or a journal. I’d literally do nothing. Which was deeply uncomfortable.

The point of solitude was to learn that I didn’t need to be productive or important to exist. It unplugs me from the world, and (hopefully) from the opinions of other people.

It isn’t a quick fix. It’s not much fun - my ego screams at me. But I did find myself learning to become comfortable just “being” myself, and not attaching my worth to my production. And I found it slightly easier to not worry as much about the opinions of others.

The flaw with “make a dent in the universe.”

I realized during this time that underneath some of this angst was a presupposition about the purpose of one’s job. The startup world is full of admonitions to “make a dent in the universe”. Most often this means build a massive startup. And while it’s galvanizing for a certain type of person, I think it’s a bad narrative for most people.

The person who is employee #50 at said startup.

The founder that fails.

The barista at my coffee shop that gives me joy every day in the form of a smile and a legal addictive stimulant.

The talented corporate executive.

The retiree.

The 50 year old woman in Honduras who doesn’t know what a startup is.

My mom.

As I wrestled with the loss of my professional identity, I realized I thought what I was doing had to be big and important. Otherwise I didn’t matter.

I had unconsciously adopted a narrative that doesn’t serve most people, and didn’t serve me.

I needed a narrative that was useful and redemptive for a lot more people.

Job / Vocation / Work / Life.

I eventually emerged with a framework that’s been helpful for me and for others in putting all this in perspective.

I call it Job / Vocation / Work / Life.

• Your job is what you do for money.
• Your vocation is what you do that gives you the most joy.
• Your work is the sum of lasting good you create in the world.
• Your life is the person you’re becoming.

I love it because it provides a proper framing for just about anyone. It has a bunch of implications:

• Your job can be your vocation. But often it shouldn’t be. I love to cook. It’s the closest thing I have to a meditative practice. I love having people over, making elaborate meals, giving that gift. But if I opened a restaurant it would ruin it. Making the same thing over and over again. Worrying about yield and margin and customer satisfaction. I’d be miserable. Cooking is a vocation. I shouldn’t make it my job.
• Similarly, your work is more than your job. The average person changes jobs every 3 years. But your work is a lifelong endeavor. You are capable of adding to your body of work in whatever job you have. Your work is anything you do with intention, consistent with your values. Raising your kids. Being a loving partner. Bringing people together. Serving your community.
• Finally, your life is just the person you’re becoming. Your job is a part of that. In fact, I believe your job is the ideal place to develop your character. You spend more time there than anywhere else. And you often have to deal with challenging situations, with challenging people, under time and money and emotional constraints. But your job is not your life.

All of them are good and necessary. They just need to be put in their proper perspective. And none more so than your job.

Your job is a tool to provide you with a living. A tool to help you develop your character. A tool to help you add to your body of work. It’s important. It’s just not everything.

Self-care matters.

It took stepping away and slowing down to realize that I had been carrying low-grade anxiety in my body for years. Even when I didn’t have anything to work on, I’d sometimes find my heart racing for no reason. It was as if I had trained my body to run on adrenaline at all times.

Once I stepped away I slowly acquired a toolkit that helped me deal with it.

• A great therapist was super helpful.
• Learning to take my sleep more seriously was helpful.
• Going for walks was helpful.
• Making healthier eating choices was helpful.
• Allowing my friends into the places of my soul that were dark and scary was helpful.

One of the best things I found was the use of another discipline, service. Getting out of my own head and trying to serve others was incredibly helpful. I found that focusing on being a good dad, a good husband, a good friend was huge.

And when I went on a 10 day trip to Honduras with my dad as part of a medical trip with his church, I found my heart had slowed down. I wasn’t somebody important trying to do big important things. I was just a guy, taking someone’s temperature, helping an elderly man walk slowly to the right exam room, helping a woman try on reading glasses. I wasn’t thinking about myself at all.

As I enter the next phase of life, I now know what anxiety feels like. I have a toolkit to address it as soon as it arrives, with service to others being chief among them. And I have a commitment to pursue a life that minimizes the chances of having to deal with it in the first place.

Figuring out what you want by starting with what you don’t want.

Eventually I started getting antsy. I needed something to occupy my energy. But what?

There’s an interesting thing that happens when you get older. You’ve acquired a bunch of skills. You’ve had roles with progressively more responsibility.

I’ve developed a relatively unusual skillset over the years. I was a designer. I was a marketer. I know enough code to be dangerous. I can write, and speak, and make pretty decks. I’ve had to run payroll and negotiate contracts and manage teams and be a leader.

In a way, it can make it harder to see what you should do, because there are a bunch of things you could do.

So rather than starting with what I wanted, I started with what I didn’t.

I looked at the next season of life with my wife and my kids. I asked what should I avoid doing, and what the implications would be.

It led me to some interesting conclusions. I realized I didn’t want to raise money or take on debt, which means prioritizing ideas that have low capital requirements and are quickly profitable - most likely a services business of some kind. I realized I wanted to try to be “the guy” after always working with partners, to see what I’m capable of. At the same time I realized I’m not interested in the “solopreneur” thing - I want to build something I enjoy with people I enjoy.

All of these pointed to ideas that in some ways are “smaller” than what I was doing, which was unexpected. But having clarity on my “why” made it much easier to avoid second-guessing.

The next thing.

A few years back Manifold hired a bunch of senior consultants from PwC, BCG, etc. When they came in, I naively thought they did their own marketing and thought leadership. It turns out they don’t. They have a robust marketing apparatus to help them create content.

So we stood up something similar. I’d get on calls each month with each of our Managing Directors. We’d riff on ideas, I’d get brain dumps from them on a variety of topics. Then myself and my marketing team would turn that into short and long-form content for them.

I learned a lot about what works and what doesn’t with marketing professional services firms. They’re not like other types of companies - you buy either from a referral, or because someone achieved “Trusted Advisor” status in your mind, usually through the creation of compelling and interesting thought leadership.

As I was thinking about what’s next, I wondered if other “boutique” professional services firms have the same issues we had.

Turns out they do. When you have a seller-doer model, your professionals are busy either closing new business or delivering on existing business. Marketing is the definition of “important but not urgent” for them.

So in Q4 of 2023, I started working with a small handful of clients to help them become “trusted advisors” to a larger audience, helping them get all the great ideas out of their heads and onto paper.

I've given presentations in the past at Techstars, Kellogg, and elsewhere on the idea of "Product-Market Fit". It's a nebulous idea - the kind of thing where you "know it when you have it."

I don't know if I have it, but it's certainly trending in the right direction. I've closed clients in a single call. I've had clients tell me our monthly calls are one of the highlights of their month - we riff on ideas (which they love talking about anyway), and it magically turns into content that sounds like them.

The feedback has been solid. I enjoy doing it. Because of my unique background I have sufficient domain knowledge in a bunch of areas - I don’t have to be brought up to speed on the topics. I know it works because I've seen it. It’s an opportunity to bake the discipline of service directly into my job. And it is consistent with all of the criteria I set out for myself when trying to figure out what’s next.

So in 2024 I’m going for it. The firm is called Madison, and its goal is to help boutique professional services firms grow.

Our main service offering is the content creation process outlined above - what I call Authority Marketing. But I am treating the next year as an extension of customer development - learning what works, what they need the most help with.

In the meantime my goal is simply to serve my clients as well as I can.

I also started writing down everything I’ve learned over the years about growing firms. I plan to start sharing all of this in the coming months.

How one’s Point of View matters, and how to create one.

How Authority Marketing works and how to do it well.

How to nurture relationships and make it easy for them to raise their hands when they’re ready.

How to systematically do upsells, cross-sells, and referrals.

How to help Director or VP level talent begin to build their own reputations and books of business, effectively creating a factory of rainmakers.

The goal is to become the best in the world at helping boutique firms grow. It’s a goal that will take at least 10 years to make happen ??.

If you’re in that world and would like to learn more, feel free to DM me. Would love to share with you how we work.

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It’s a strange thing to start over. But it’s also exciting. While one could argue it’s smaller than what I was doing before, what I was doing before started out small as well. And while many of my startup friends find it odd, I actually really enjoy client work.

If my ambitions grow over time, so be it. A services business can be a great base to build off of, as companies like Tiny (and Manifold) have demonstrated.

But for this next season of my life, my job is simply to build a company that serves its clients better than anyone else they deal with.

I plan on documenting the journey in some fashion, in case it’s helpful for others. I also plan to write a lot more about professional services firms, so don’t be surprised.

I plan to continue to be helpful to others however I can, whether that’s helping them improve their pitch decks, or doing my once a year coaching program, or just sharing advice on company building.

Most importantly I plan to continue doubling down on my relationships with my kiddos and my wife, working on becoming a progressively better person, and building intentional businesses while helping others build more intentional lives.

I’m grateful to my former partners, who I still care about deeply and am rooting for. I’m grateful to all the folks I worked with during that phase of my life. I’m grateful to my wife for supporting me through this strange and sometimes uncomfortable process. I’m grateful for a small group of wise friends who’ve helped me navigate the maze of ideas and emotions. And I’m grateful to my early beta clients for taking the risk and helping me get things off the ground.

Here’s to an exciting 10 years.