Five Unusual Lessons From Building Two Billion-Dollar Companies
A lucky operator’s guide to lessons from the trenches that help you build a business you actually love
When I was growing up in India, I didn’t know how many zeros were in a million. A billion might as well have been imaginary.
Somehow, life conspired to let me do it twice.
Once with Teles Properties, which started as a small real estate brokerage and grew into a multi-billion dollar business which we eventually sold to Douglas Elliman. Then again with Real, a publicly-traded company on the Nasdaq that scaled faster than anything I had been part of before.
People assume there’s a playbook that guarantees this outcome. There isn’t. There are only a few core lessons you get tattooed onto your brain the hard way.
I’m sharing these five not because you should try to build billion-dollar companies. That part is optional. But if you want to build something worthwhile, these might help.
1. Bigger is not better. Better is better.
At Teles, the promise was clear:
Our platform would save agents one day a week.
What could they do with an extra 52 days a year?
Every decision ran through that filter.
At Real, it was a similar discipline.
The mission was to make agents' lives better. Being publicly-traded also meant thinking about quarterly earnings while staying true to that promise. Every time we debated expanding, launching a feature, or changing direction, we asked: does this make the promise more real for the people who said yes to us? That is really the tradeoff.
And I am sorry to tell you, its really hard sometimes.
Bigger can give you resources and momentum to deliver better. But if what you deliver isn't great, bigger just means more people see it fail. That creates frustration, resentment and often, irreparable broken trust. In the end, better will always win.
My biggest learning is that you have to care about building something so good, so elegant, and so freaking amazing that you are extremely proud to show it off to anyone. That's when you know you have better. If all you find yourself talking about is revenue or growth numbers, it might be a sign that you've drifted from what really matters.
It maybe a sign that you are serving the wrong master.
Bigger is not better. Better is always better.
2. Complicated solutions hide simple problems.
If you ever want to feel important, build something that requires a 50-slide strategy deck to explain.
We tried it. It worked about as well as you’d expect.
Complexity is often a sign that you’re avoiding something obvious.
In a growing company, simplicity doesn’t happen by accident.
You have to fight for it.
The more complicated something sounds, the more likely someone is procrastinating or covering up uncertainty.
Sometimes that someone is you.
3. Culture is the real leverage.
The companies grew because a small group of people treated the mission as their own.
When you find people who care deeply, the math changes. Super fast.
Culture shows up in what you tolerate, what you celebrate, and what you ignore.
I’ve missed the mark plenty of times. But when you invest in culture early, you can fix almost everything else later.
If you don’t, no strategy will help you.
At Acquisition.com, we have 6 words that guide our culture:
Competitive Greatness
Sincere Candor
Unimpeachable Character
This is everyday vocabulary for us… in our slack channels, on our zooms, in our memos and during our hiring. Clearly nobody can be 100% of it 100% of the time, but it provides for a no-fluff diagnostic for who we are and how we show up. Operationalzing culture is a core part of building a billion dollar business that you are proud of.
4. Make your goal specific enough to reverse-engineer.
At Teles, we decided to 10x the business in five years.
It sounded absurd.
But we didn’t stop at a big slogan. We broke the goal down to a daily number: $8.3 million of sales each day. Once you see it that way, you can work backward to figure out exactly how many appointments, conversations, and contracts it takes.
$8.3 Million x 365 Days = $3 Billion+ for the year
(Yes, we generated revenue 7 days a week for those who think my math is off)
That clarity changes how people show up and most importantly nobody wonders what winning looks like.
Because when you turn the goal into a KPI and then build a system for it, even the most unreasonable thing feels achieveable.
If it's worth doing twice, build a system for it.
We also built a cadence of accountability.
Every day, on a 15-min sales huddle, every sales manager reported two numbers: what got booked yesterday, and what was committed for today. That was the cadence that drove our entire growth. I know it seems ultra-boring, but I am here to just report the truth.
I learned the hard way that most ceilings are self-imposed. If you translate your ambition into something you can measure daily, it stops being theoretical. It stops feeling unachievable. It looking unreasonable. It starts to just feel like what was always meant to be.
I am trying to give you a formula so that it doesn’t feel so woo-woo!
5. Design the conditions for success.
It’s easy to set a goal.
It’s harder to build the environment that makes the goal inevitable.
One question that helped us was:
What is true in the life of a person or a company that has already achieved this?
If you want to lose twenty pounds, what would be true in your life? Maybe there’s no junk food at home. Maybe you train four days a week. Maybe you have accountability.
Business is no different.
At Real, we looked at what would have to be true if we were already the fastest-growing brokerage in the world. Then we designed our growth systems and incentives to match that reality before it happened.
Most people don't have a business problem. They have a sequencing problem.
Meaning:
Getting the conditions right often matters more than any one tactic.
The Boring Truth
I’ve spent years learning how to build billion-dollar companies. And honestly, 90% of it is the same as building a $1 million company. But some days, I still think about that night I was so broke I fought a raccoon in a dumpster for Pop-Tarts.
Strawberry Pop-Tarts.
Nobody writes about that part.
They write about funding rounds and ringing the Nasdaq closing-bell, but not about sitting alone, wondering if you’re making a giant mistake. If all of this is going to come crashing down and you are left holding the bag… not to mention the public disgrace, the personal shame, and the years of therapy that would come after it all.
The truth is, every big outcome is just a stack of small, unglamorous decisions you repeat when nobody is watching.
Because:
Until you win, effort always goes unnoticed.
It’s choosing the better hire over the convenient one
It’s picking up the phone when it would be easier to hide behind email
It’s staying cool when the numbers look bad and making a plan
If there’s one thing I hope you take from this, it’s that you don’t have to be extraordinary to build something extraordinary.
I am living proof that ordinary works just fine.
You just have to decide what you want your life to look like if you’ve already won, and then start acting like it’s true before anyone else believes you. You have to be a little delusional. A little crazy. And just little neurotic to believe that you can do it.
Just a little.
Because eventually, if you do it long enough, reality has a way of catching up.