The Secret Sauce of Valuable Service Businesses

Robert Smith of Vista Equity Partners famously said, “Software companies taste like chicken. They’re selling different products, but 80% of what they do is pretty much the same.”

Service businesses are no different. 

You buy someone’s labor, mark it up, resell it, and spend opex to operate the business. You also spend money on capex to improve the “infrastructure” of the business, and what’s left over is your profit.

Markup – Opex – Capex = Profit

The challenge is that in the long term, the free market is annoyed with your business model.

Customers and labor don’t fully understand the role that you serve, and they don’t particularly care that you have to spend money to operate the business.

Labor doesn’t like you marking up their time, and customers want your markup in their pocket. Many suspect they would be better off if the service were cheaper, and you were removed from the equation. 

To be loved by customers and labor for your middleman role, you must be obsessed with creating more value than you mark up.

Value Provided > Markup = Happy Customers & Labor = Durable Business

You create “excess value” by building value-adding infrastructure (less jargony explanation below), which eventually leads to reliable, growing profits and the option to exit.

Creating Value Through Infrastructure

At the start, almost all the value created in a service business comes from the unique talents of you, the founder. You create trusted relationships and clients happily pay the markup knowing that you are “watching over things”. You use your special magic aura to make everyone happy, and it is a great way to get initial traction.

Unfortunately, businesses dependent on “founder magic” are difficult to scale and have almost no external value without the founder in place. To become something more than a great job for the founder—to become a true asset—the business has to evolve and create more durable, transferrable value through infrastructure.

Value-adding infrastructure :

1. Enables labor to be more efficient and productive. A worker can do more work, more easily because of the tools and structure you provide.

Examples: Custom software matching labor with jobs and helping them efficiently manage their projects, so they can take more jobs.

2. Enables labor to be higher quality and more consistent. A worker can do better work, more consistently because of the tools and structure you provide.

Example: A proprietary process to deliver your services, codified by “How To” guides and training courses for your labor (and often supported by software).

3. Enables labor to be consumed by customers in a more frictionless, more enjoyable manner. The sales and operational process that allows for labor to work with the customer is “lower toll” and has a higher probability of success for all parties.

Example: Digital marketing campaigns that attract quality customers to your business and a website that makes it easier for clients to educate themselves on your services. Training and materials for sales people to improve communication with customers and speed up sales cycles. Elaborate self-service flows that allow customers to solve problems quicker and easier on their own.

Infrastructure creates value repeatedly and reliably. 

But infrastructure costs money, and if you’re bootstrapping or you’ve acquired the company, you’re on a budget. You are paying operational employees who keep the trains running, trying to grow sales, trying to feed yourself, and paying taxes on every dollar the business earns.

You need to be strategic about how and when to invest in infrastructure – the first priority is always survival.

Here is what building infrastructure looks like over the lifecycle of your bootstrapped service business (with some examples in italics):

1. Startup Phase – The First 2-3 Years

You need to survive, scale gross margin, and add talented employees as quickly as possible. Scale and talent begat infrastructure. 

You do not need the same kind of infrastructure that you see in a company ten years old. You don’t need expensive CRM implementations, complicated HR systems, or detailed employee handbooks. It is ok for the business to feel a little sloppy at times and for quality to be inconsistent.

Pay yourself as little as possible, as long as possible, so you have more money to hire people who will help you grow. Hire people who are undervalued and hungry, and build a culture that focuses on improving the business, with no regard for petty ego. 

Example: We hired as quickly as possible, and we didn’t pay ourselves over $60,000 until year 6, when we were up to 10 employees. The excess early capital to hire was critical to the long-term success of the business.

Infrastructure should only by built to resolve massive operational inefficiencies, and should be mostly employee, not vendor, driven. 

Example: The top sales person spends three days creating wonderful email templates for the team that save everyone two hours/day.

Do not feel like you have to reinvent every part of your business – the competition are smart too, and sometimes it makes sense to follow their lead. Bonus tip – avoid anything HR as long as humanly possible – it is like trying to sail a boat with the anchor still in the water.

2. Find “Product/Market Fit” Phase

In the middle years, build infrastructure for what works, but don’t get sucked into big investments for new ideas.

The middle years of your business, roughly years 2-7, are an awkward adolescence. You exist, but you’re not truly excellent (as you might have hoped you were in the start). You are probably selling at least one service well, but you suspect there is a better way that the business could evolve. You’re getting a little impatient that you’re growing steadily, but nothing like a hot startup. You’re still pretty poor. 

You are testing different markets, different services, different customer acquisition strategies, different operating models. You are trying to bring up the average of your employee group and figure out who can lead you into the next decade. You’re actually starting to understand your market and the players involved, and you are exploring the space with earned confidence. 

These middle years are when you’re trying to figure out what exactly the business is, and what flag you want to plant that says “we are the best in the world at XYZ”. 

Example: We started a second brand four years into building the business because we started to realize the limitations of our original model (in-person, academic tutoring focused on LA/NY). We eventually buried the original business and went all in on the new business (online, test prep tutoring, originally focused on international), which is what was ultimately acquired.

Avoid the temptation to really invest in infrastructure for the new ideas until you get some kind of positive market signal. “Fake it ‘til you make it” usually can buy you some time. Stick to building for the old part of your business that pays the bills, even if it is a little boring.

No matter what, you’ll build infrastructure that you have to throw out. Try to avoid the sunk cost fallacy and just let it go. All that matters in this stage is using your earned expertise to narrow and clarify your vision for the business.

3. Scale and Build Infrastructure Phase

Once you have arrived at your supreme focus, “we are going to be the best in the world at XYZ”, then it is time to build the infrastructure that supports that vision and maximizes that process.

Example: Around year 7, we decided we wanted to be the best in the world at one-on-one, online, SAT & ACT tutoring. That meant building a curriculum for this purpose from scratch. Not the norm of adapting a classroom curriculum, or taking in-person curriculum and moving it online, but thinking from the ground up, from first principles: “what is the absolute best way to improve scores in the least amount of time, with a one-on-one, online delivery method”. Building this was a 5-7-year beast of a project, with constant iteration, but the end result was a completely unique piece of infrastructure that added crazy value to our tutors and clients.

You have to improve the infrastructure supporting every single piece of the value chain from the time your labor comes to interview until they finish an engagement with the client. Each step must be codified and optimized. Always try to use software and systems instead of humans.

Create KPIs for your systems and hold people accountable. If you invest in a new CRM, can you demonstrate that salespeople can now handle more leads? Do those new leads convert into gross margin? A great metric for overall efficiency is revenue / corporate employee, or even better, revenue / salary $.

Example: We built custom business management software that helped us double revenue/employee from year 7 to year 12. Caveat, supporting a software development function is very expensive and difficult. Only build software that is absolutely unique to the way that you run your business and will make the business significantly more profitable long-term.  

Building infrastructure is a long term process. You are building a house, room by room. You will have to make tradeoffs and prioritize one pain point over another. Be patient, and try to explain to employees the overall vision.

4. Profitability Phase

It is very hard to rapidly grow a service business, build real infrastructure, and actually make money. There is always something new to invest in. 

At some point, you have to be willing to stop building everything, decide your product is “good enough” (verifying this assumption every year), and consolidate your gains. Transition employees out of infrastructure building and into roles that grow revenue, or gently sunset their projects so they have opportunities to find new work. 

After consolidation, you will have“core profitability” (e.g. true profit margins of 20%+) and infrastructure that can scale. This gives you lots of options – sell the company, step back, or reinvest in new salespeople and other growth areas. 

It is easier said than done—I basically had to step down and deputize my successor CEO to this final task because I couldn’t handle the shift to a profitability mindset.

Happy building!

Entrepreneurial Motivations: Light and Shadow Forces

The best reason to start a company is to solve a problem that you genuinely, to your core, care about, and you can’t see another way to do it. People who find this are truly blessed.

And then there are the rest of us, and we are complicated. Here is my take.

The motivations for starting a company are complex – there are “light” and “shadow” forces. 

What can seem light:

“I want to make a positive impact on the world!”

“I want financial independence so I can spend more time with my family!”

Can also have a shadow component:

“If I make an impact on the world, I will finally feel self worth and the respect of my parents!”

“I need as much money and power as possible to give me feelings of safety I’ve never had!”

In my early 20s, my professional motivations were a poorly understood soup of light and shadow forces. I’d roughly characterize light forces as “needs pursued from a happy, authentic place” and shadow forces as “needs craved from an unhappy, incomplete place.”

I had a vision for my life that ended with a 20 hour work week by my mid-30s, a comfortable suburban existence, and plenty of time to spend with my future kids. I also desperately wanted to feel a sense of adventure – it was less about the money, more about the freedom, fun, and unpredictability.

Becoming an entrepreneur, or “going into business for myself”, seemed like the best way to achieve this future, so I picked that as my aspirational identity.

There was real joy in building a business. I loved finding talented people and being their best (albeit gruffest) cheerleader, and I loved playing a part in creating good jobs and putting a top quality product out into the world.

I loved the feeling that my life had some momentum and that every year would be different than the next. My business partner Tim is my childhood best friend, and being able to play the game of business with him is a real pleasure.

There are cracks in the story though.

Behind every light need there was a shadow craving, originating from a wound and an unhappy place.

Light: I wanted to feel empowered to shape my career towards my goals.

Shadow: I lost confidence that I would ever be “picked” by an elite institution whose status I could attach myself to in order to feel worthy. I had a deep anger and distrust towards authority.

Light: I wanted to be “in the arena”, living a true adventure, experiencing all that life had to offer.

Shadow: I wanted to think of myself as someone who was in the arena. Egoic grandiosity lurked behind many ambitions, telling me I was heroic and writing a superior “story” for my life.

Light: I was full of ambition and super excited to create something “real” in the world that I owned a part of.

Shadow: There was a lot of fear that I would fail at achieving my ego’s chosen identity. The fear could be extremely productive, but it could also be poisonous. I woke up anxiously in the middle of the night, and I would drive home from work with my face sore from clenching it all day. Anger was great fuel, but anger cut me off emotionally and made me numb.

Light: I wanted to feel autonomy over my time and financial future.

Shadow: I really didn’t want the pressures, constraints, financial limitations, and long hours of what I imagined a corporate job to be. I had to find some way to make money that just wasn’t that. Entrepreneurship was as much escaping that life path as it was running to building businesses.

It was messy business trying to get deep unmet needs met through my professional life, and the light/shadow cross currents were very confusing. 

Suffice to say that what seemed like a simple choice at 25 looks a lot more complicated at 39.

So, what?

The truth is, I’m still working on figuring out what to make of all this. Shadow motivations were extremely useful in the difficult parts of my early career, and I don’t know if we would have made as much progress without them. As Josh Wolfe says, “chips on shoulders put chips in pockets”.

However, as I got older, the negative side effects took a toll on my personal and professional life. Having so much fear and anger in my motivational stack just wasn’t working for me anymore, and it became painfully obvious that I had to address some areas of real neglect. Playing detective with my own web of motivations has been deeply helpful for my own growth.

If I had to leave the prospective entrepreneur with one thought (that I would have absolutely ignored at 25) it would be:

“The reasons you want to start a company are probably a lot deeper and more complicated than you think. You’ll learn a lot about yourself when you’re ready to try to figure them out.”

Build Your Company to Exit

If your long-term goal is to move from labor to capital, then you need to build your business into an asset that you can personally “exit”, not a high paying job.

Assets can be sold or held once you have exited, but they do not require your day-to-day participation. Assets give you free time and capital to invest.

The “gravitational pull” of a service business is to stay small, never let the owner leave operations, and never be acquirable for more than 2-3X EBITDA (if at all).

You have to fight this gravity by:

1) Focusing on a niche and creating actual moats in the business

2) Building the organization and management to be independent from you

Moats and Niches

When you are the driving force of your company, it is easy to be in the “we do stuff for money!” business.

Your relationships and insights drive new opportunities, and your can-do attitude pushes the company to say “yes” to everything under the sun.

Take your time to understand the market and opportunity set, but to set the stage for an eventual exit, make a decision and say “we will be the best in the world at XYZ”. It took us six years to really focus in our first business, and everything was easier after that.

XYZ can be a simple as “providing the most delightful high-end residential lawn care services in North Manhattan Beach, CA”, but you have to plant a flag, say “we will OWN this space”, and relentlessly execute towards the mission.

This clarity will make your company simpler to operate, more profitable, and easier to exit.

You can focus on building a defensible moat, and it will also happen organically. No company in the world will care as much about your customers and be willing to completely align their business around this vision.

You can eventually replace yourself as CEO because the existential issues that require the founder will be resolved, and the focus will shift to operations and efficiency (which employees can often do better).

You have a tight, secure story. You are a solid, hardened entity, built around serving a customer better than anyone else, not the talent of the founder.

You will build something that a competitor would love to own, or a financial buyer would feel comfortable borrowing against to buy. Your business feels like a bond, not distressed equity, and you have the flexibility to sell or own from a distance.

Organization and Management

For every “job to be done”, you need to eventually replace yourself with someone who is better and less expensive (taking into account your equity compensation), until one day 5-10 years later, you’re out of work. Then you can exit.

You learn the job, you build the initial processes, then you hire and train someone else to do it. The people you hire should take those existing processes and rebuild them in a much better way. Each new person you hire should “bring up the average” of the company operations and talent pool.

Each time you take a job off your plate, find a new, harder job that better aligns with your strengths and is needed for long term growth. The challenge is to allow yourself to really delegate, even the hard stuff.

You have to keep pushing, hiring, growing until the company finds product/market/distribution channel fit and reaches a scale and stability that can support a new CEO.

Building an independent organization is a long, slow grind, but it is possible. It pays to be a bit lazy with a middling self opinion, so you’re less attached to completing tasks on your own and more open to promoting other talent. It took four years for my co-founder Tim to be able to exit, and nine for me.   

Some of the challenges:

1) Every time you replace yourself in a job, their salary comes straight from the business profits, and it makes you more poor in the short term. When you are growing and hiring a lot early on, all money conspires to be taken out of your pockets. We made just enough to survive our first five years.

Embrace financial constraints, start young, live your Minimum Viable Life.

2) You have to attract, hire, and retain great people to take over important roles at your extremely irrelevant and mediocre paying small business. 

Offer more than just a paycheck. Offer fun, offer comraderie, offer adventure, offer flexibility, offer opportunity, offer humor.

3) You always feel like you suck at your job. Once you have figured out a job, then someone else can be trained to do it. You move on to the next new thing that needs done, and now you suck at that. At least you can eventually “trade up” to areas of more strength and delegate the parts of your job that you hate.

Be humble, have a sense of humor, and enjoy that you’re growing. It gets better.

4) Eventually, you’ll find a job that you’re actually really good at, and there will be a negative tradeoff required to replace you. The business will be a little bit worse in order for you to exit that role.

This is the price you pay to exit. You have to just let this go. You can’t be a perfectionist and exit your business.


I talk about a lot of these concepts on Eric Jorgenson’s podcast if you’re interested:

He also writes a ton about the concept of Leverage, which is a valuable framework to think about on your professional journey:

You, Inc – Getting Into Business

Wake up every day, consumed by “You, Inc”.

If your goal is to make the leap from labor to capital, from selling time to making money with your assets, then get into business for yourself as soon as you can. 

Don’t get into the perfect business, don’t get into your life’s work, just get into business.

Wake up every day, consumed by “You, Inc”. Have every thought process working towards your north star, building your little empire.

This journey is not about achieving your professional potential or even being happy – it is the singular goal to gain independence over your time and money. 

You can build your snowball from the smallest flake, but there needs to be something to grow from.

The biggest threat to the dream of independence isn’t picking the wrong type of business, it is procrastinating. It is never starting at all.

The earlier you start, the more time is on your side. The less money you need to live on, the more capital you deploy into opportunities with bigger upside. 

You just have to start. A business you own that is boring and unglamorous is better than no business at all. You have to start owning things, owning your time, and growing as a businessperson.

When you work at a job and you’re young, you make very few real decisions. When you own a business, you make real decisions every day and suffer/reap real consequences. 

Those reps compound rapidly, and over time you build earned, hardened judgment. You make better decisions over You, Inc, and the value builds.

People recognize that you’re “in the game”, taking risk and building. New opportunities come your way.

Over time, you leverage your labor less, and your judgment more. You allocate your time less, and your capital more. The snowball will build if you tend for it every day, but you have to start with something.

Two Major Ways We Can Help Small Businesses Grow

I thought long and hard about what would most help a Bootstrapped Service Business (“BSB”) like ours grow faster and create more jobs, and it all comes down to improving access to meaningful investment capital – not small changes to tax rates, increasing deductions, payroll tax holidays, or tweaking regulations

‘Tis the season for tax reform, and in tax reform season, politicians talk about how changing the tax code will help small businesses grow and create more jobs.

I thought long and hard about what would most help a Bootstrapped Service Business (“BSB”) like ours grow faster and create more jobs, and it all comes down to improving access to meaningful investment capital – not small changes to tax rates, increasing deductions, payroll tax holidays, or tweaking regulations (which doesn’t even help if you happen to be a vassal with a feudal lord like the state of CA or NY…side gripe for another time).

Continue reading “Two Major Ways We Can Help Small Businesses Grow”

Liquid Net Worth may be a Better Basis than Income for Income Tax Rates

America does not have an income inequality problem so much as it has a wealth inequality problem. The top 1% make about the same total income as the bottom 40% combined, which is significant, but it is nothing compared to the wealth gap.

The top 1% have 139x as much wealth as the bottom 40%.

So, why are income and capital gains tax rates based on income, not wealth? This is an outdated and oversimplistic way to ballpark wealth, and modern technology makes it much easier for track wealth now than in the past. 

If we want to devise a more sensible tax system, we should strongly consider basing income and capital tax rates on a metric I will call Liquid Net Worth, instead of the traditional “taxable income”. This ensures that tax rates are assessed on a more full picture of someone’s financial situation, not just their year-to-year income.

Continue reading “Liquid Net Worth may be a Better Basis than Income for Income Tax Rates”

Government to Business – “Robots, Not Humans, are the Workers You Want”


Ever since sharing economy companies burst on to the scene, there have been disputes between governments, like the State of California, and companies, like Uber, about the employee/contractor classification of its workers.

Some companies surrendered (Instacart), a few are still fighting (Uber), and some had to shut their doors because of the changes (Homejoy).

None of these policies are good for the long-term of labor in America. They massively discourage entrepreneurs from building business that revolve around human workers, and they accelerate the transition to a job-lite world that is built on robot, not human, labor.

Continue reading “Government to Business – “Robots, Not Humans, are the Workers You Want””

Does “Cleverness” Lead to Superior Cash Returns? Venture Capital Cash Returns v Stocks and Bonds

Analysis of actual cash distributed to limited partners versus stock and bond performance from 1981-2006

There are a few people in the world who are lucky enough to be clever for their job – a job that pairs an excellent salary with extremely high upside.

Well-funded entrepreneurs, venture capitalists, private equity investors, and hedge fund managers are all put to work in the hopes that their cleverness will deliver outsized returns for limited partners (or investors in the case of entrepreneurs).

Continue reading “Does “Cleverness” Lead to Superior Cash Returns? Venture Capital Cash Returns v Stocks and Bonds”

Confession: I Don’t Think Uber is Actually a Great Business (Yet)

Additional Background If You Stumbled on this Post Randomly

Uber is everywhere – especially in the startup/technology world that I follow closely, mostly through podcasts. It is the source of deliciously spirited debate because it is a wonderful blend of ubiquitous consumer product and highly publicized startup juggernaut. And whenever I get in too many debates with people about one topic and get stuck on a plane with no wi-fi, I write out my arguments, which I occasionally publish and commit to the public record. 

Continue reading “Confession: I Don’t Think Uber is Actually a Great Business (Yet)”

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