Four years ago, I walked away from a corporate job making over $500,000 per year.
I was 28 years old.
I actually liked my job. I worked with great people, had an incredible mentor, and was one of the youngest executives at the company.
If I stayed, I probably had a pretty clear path to making $500K+ annually for a long time.
But on September 30th, 2022, I left to build my own business.
Four years later, I've made money, lost money, started businesses, shut things down, watched deals work, and watched plenty fall apart.
But the biggest thing that's changed isn't how much money I make.
It's how I think about time.
At 28, I was trying to make as much money as possible and take advantage of every opportunity.
Today, I'm much more interested in building something I want to own for the next 20 years.
Here's what changed.
I recorded a 12-minute video breaking down what I've learned over the last four years. You can watch it below, or keep reading for the full breakdown.
1. My corporate career was probably the best preparation I could have had
I spent about seven years in corporate America, mostly in sales and sales leadership.
I started as an SDR making cold calls and sending cold emails.
My first partial year, I made around $37,000.
Then $110,000.
Then $250,000.
Eventually, I was making over $500,000 annually.
I got my first six-figure commission check when I was around 24.
But my lifestyle never really caught up with my income.
I had roommates, worked constantly, traveled mostly for work, and started buying single-family rental homes.
I never viewed sales as my final destination. It was a way to make money, learn valuable skills, and figure out what I wanted to do next.
When I eventually started raising capital and building businesses, I wasn't starting from zero.
I already knew how to reach out to people, build relationships, handle rejection, and sell.
I was just selling something different.
2. I didn't quit my job and then figure out what to do
For roughly 18 months before leaving corporate, I was building Silverman Capital on the side.
I'd work my corporate job during the day and spend nights and weekends building the business.
There wasn't much balance.
But by the time I left, we'd already helped raise over $40 million.
We had investors. We had deals. We had a real business.
Personally, I had a few hundred thousand dollars in cash, investments producing cash flow, and relatively low living expenses.
I wasn't trying to take some massive leap of faith.
I was trying to make the decision as low-risk as possible.
I wanted enough runway that I wouldn't have to go back to corporate.
And this is where I think a lot of high earners get trapped.
You can make $500,000 a year, but if you've built a lifestyle that costs $450,000, leaving becomes incredibly difficult.
Your income is huge.
But so is the amount of money you need to replace.
Keeping my expenses relatively low gave me the ability to take a risk I otherwise might not have been able to take.
3. Making more money isn't always the right goal
When I first left, I said yes to almost everything.
Investor calls, consulting, networking, deals, new businesses, you name it.
At one point, I was personally taking more than 30 investor calls per week.
And there were plenty of opportunities to make money.
Consulting is a good example.
If you can charge $500 or $1,000 an hour, that's incredible money.
But eventually I started asking myself a different question.
Do I really want to spend the next 20 years selling pieces of my calendar?
I left corporate because I wanted ownership.
Replacing a $500K salary with a high hourly rate wasn't necessarily going to get me what I wanted.
So I started thinking differently.
Instead of asking how much money something could make me this year, I started asking whether it was something I wanted to own for 20 years.
Would the equity compound?
Would the brand become more valuable?
Would the business become less dependent on me over time?
Sometimes that means making less money today.
We've made decisions in our businesses where we could have taken more money upfront.
Instead, we've chosen structures we believe are better for investors and for building long-term trust.
I'm much more interested in building a business that's worth significantly more in 20 years than maximizing what I take home this year.
4. A good investment isn't necessarily a good investment for you
Real estate is a great example.
When I first started investing, I viewed real estate as a place to make money.
And I still think it can be an incredible asset class.
It can preserve wealth, produce cash flow, and offer meaningful tax advantages depending on your situation.
But I've realized that something can be a great investment without being the right business for us to build.
Just because we can do a deal doesn't mean we should.
Today, I spend a lot more time thinking about where we actually have an advantage.
Why should we be the ones doing this?
What can we do better than other people?
Is this taking time away from something more important?
Those questions have probably eliminated more opportunities than they've created.
And that's been a good thing.
I'm less interested in building ten different businesses.
I'm more interested in building a few businesses that can become much bigger.
5. Walking away from a deal is sometimes the best investment you make
Recently, we spent months working on an acquisition.
Our team put a ton of time into it.
We spent money on due diligence, quality of earnings, travel, and other pursuit costs.
The deeper we got, the less comfortable we became that the historical financial performance represented where the business was actually heading.
It was still a good company.
But not at the price we were going to pay.
So we walked away.
Years ago, I probably would have been obsessed with all the time and money we'd already spent.
Today, I look at it differently.
I'd rather spend money finding out a deal doesn't work before buying it than find out after we own the company.
Things still go wrong.
Deals fall apart. Markets change. Projects take longer than expected. You lose money.
But after going through enough of those experiences, you realize you can handle them.
And you get better at knowing when to stop.
6. I value cash and liquidity much more than I used to
One thing I didn't fully appreciate when I had a corporate job was how valuable predictable income is.
When I was making $500K a year, I knew money was coming in.
Entrepreneurship is very different.
There are periods where you're making a lot of money.
And there are periods where you're putting more money into your businesses than you're taking out.
That's changed how I manage my personal finances.
I keep significantly more cash available today than I did when I had a W-2.
Not because I think cash is the best long-term investment.
But because I never want to be forced into making a bad business decision because I need personal liquidity.
Being able to stay in the game matters.
And I think that's something a lot of people underestimate.
If you have a corporate job making $300K, $400K, or $500K per year, and you actually enjoy it, that's an incredible position to be in.
Keep your spending reasonable, invest a meaningful portion of your income, and let that money compound.
You can build an unbelievable life doing that.
Entrepreneurship isn't automatically the better path.
It's just a different one.
7. The ownership bet is still playing out
Something I think is important to acknowledge is that four years later, the bet I made on ownership hasn't completely paid off yet.
There were years after leaving corporate where I made less cash than I would have made staying in my old job.
This year, we're on track to finally exceed what I made in my best corporate year.
And next year could be dramatically higher.
But who knows?
That's part of the deal.
I didn't leave just to maximize my income in year one, two, three, or four.
I left because I wanted to build and own something.
And four years isn't very long when you're trying to build a business you want to own for 20 years.
Today, one of my biggest priorities is building a company that doesn't require me to personally do everything.
Hiring better people.
Delegating more.
Building systems.
For years, I got really good at doing things myself.
Now I'm learning how to build an actual company.
And I have a lot left to learn.
The biggest change after four years
At 28, I was in a rush.
I wanted to make more money, meet more people, do more deals, and take advantage of every opportunity.
At 32, I'm still incredibly ambitious.
But I'm thinking much more in decades than months.
I want to build a company that investors trust for a long time.
I want to own businesses that can compound in value for decades.
And I want to build a life where money eventually stops dictating the decisions I make.
I'm not completely there yet.
But I have a much clearer picture of what I'm trying to accomplish.
If you're sitting in a corporate job wondering whether you should leave, I'm not going to tell you to quit.
Look at your spending, your runway, the skills you've developed, and what you're actually going to do next.
And understand whether you can emotionally handle the uncertainty.
I knew what I wanted, and four years later, I'm very glad I made the decision.
But I think the biggest thing I've learned is that you only have so much time.
At some point, your ability to say no to opportunities becomes much more valuable than your ability to say yes.
Four years ago, I was trying to figure out how fast I could get somewhere.
Today, I'm trying to figure out what's worth spending the next 20 years building.
And how to stay in the game long enough to actually do it.
