Back to My Thoughts

To raise or to bootstrap?

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To raise or to bootstrap?

Before answering this question, it's worth acknowledging what we've accomplished so far:

  • 2022: Launched our first MVP.
  • 2023: The first MVP failed. We pivoted into discovery mode for Loanscape, designed the product, and started coding.
  • 2024: Launched Loanscape and secured four paying customers.

Up to this point, we’ve raised only $50K and focused on generating revenue. I’ve paid myself just enough to stay default alive while dedicating all my time to this venture.

Over the past few years, we’ve been immersed in the industry—talking to customers, studying overlooked areas, and feeling the pulse of the market.

The product we’re building today is just the beginning of that vision.

Two Paths Forward

The question we are trying to answer (and by "we", I mean me...HA) is what route to take. Do we go down the bootstrap route or do we leverage VC to make this business into something really big.

1. Bootstrapping

One path is we build a profitable business that grows to $5M–$10M ARR in the next few years and exit for tens of millions. That would make both Evan and I wealthy.

2. Venture

The other path is to raise capital, shoot for the moon, and aim to turn Loanscape into a unicorn.

Can We Bootstrap?

Yes, in theory. But it would be painfully slow.

  • It would likely take 18–24 months just to get the product to a point where we could scale.
  • I’d need to get a job and work on Loanscape on the side. That would split my focus and slow everything down.
  • The business could end up facing a slow death—not due to failure, but because we couldn’t move fast enough.

I think with bootstrapping we are investing our own resources. Currently, I don't have enough cash to bank roll development on my own. I do have TIME which is my most valuable asset at this time.

I can invest my most precious resource, my time into this business and be dedicated to building this thing into an industry defining company.

The Risk of Venture

The other path is to raise capital and take the big swing. If we succeed, we reshape an industry. But there’s also the risk of over capitalization and ruining what could have been a great bootstrapped business.

For me, this decision isn’t just about money—it’s about time.

I can always earn more money, but time is my most valuable investment. Either I bet on Loanscape, risk my time, bring in capital partners who believe in our vision and go all in, or I invest my time somewhere else.

A Personal Reflection: The Regret of Not Applying

As I've been thinking about this decision, it reminds me of a choice I made in high school.

I wanted to go to MIT. It was the dream for a nerdy engineer like me.

But everyone around me told me to play it safe. ASU was cheaper, closer to home, and made more sense logically.

So I never even applied to MIT.

Do I regret it? No. I made great friends at ASU. Some who have shaped my life more than they will ever know.

But years later, when I met people from MIT and Ivy League schools during my time at Goldman, I realized something: They weren’t that different from me. Some had done less than I had in high school, yet they had taken the shot and got into those schools.

It gnawed at me that I hadn’t even tried.

Who would PK be if he had gone to MIT, Stanford, or another top school? I’ll never know.

What stings the most isn’t that I didn’t get in—it’s that I never even applied.

This Time, I Apply

The most common advice I hear from founders who took the venture path?

Consider bootstrapping

There is regret in the air about where their businesses ended up after raising lots of capital and going down the venture path.

Maybe they weren't prudent?

Maybe they followed the herd and raised excessive capital?

There's likely a lot to learn from the failure of venture backed businesses.

But when it comes to our space, I’ve done the work.

I see the opportunity. There’s a huge market waiting to be disrupted. The path ahead is HARD—but I enjoy solving hard problems.

To me the biggest risk isn’t failure, the biggest risk is regret.

I also know that if I'm not the one who does it, someone else eventually will and it will gnaw at me knowing that I didn't take the swing when I had the chance.

Fear of failure and discomfort

I've also done some reflection around my own resistance to raising capital. When I look there, it comes from not wanting to be dependent on others. Not wanting to ask for help when I need it.

Avoiding the discomfort of asking for money. But here's the thing, everyone who's raised capital has had to confront that discomfort and fear of failure, the constant rejection.

If they believe in what they are building, then they have had to confront those issues too.

When I'm 80...

When I'm 80, I don't want to sit on the rocking chair and recite a story of how I started a business in my 20's but I let my insecurities drown out my courage to build it into something great.

So now, I ask myself

Do I take the safe bet again? Or do I "apply" this time?

This time, my gut tells me I take the swing.

A story from the past

One of my key skills is around seeing solutions to problems other people don't see. I remember at Make-A-Wish there was problem we were solving where Make-A-Wish would get airlines points donated to them. They would use those points to book tickets for granting wishes.

I spent 3-5 weeks using the simplex method to come up with a complicated solution but it kept breaking and I couldn't find an optimal solution. The solution was void of the human impact.

Then one day in the shower, I had the thought of getting rid of the complicated solution and just using the concept of "First in first out". Where any of the airline points request that came in first would get fulfilled first and the points would get full depleted.

Keep in mind that every year there was $50-65K of points going unused because there was a human in the process that was the "algorithm" of who got points and who didn't.

I suggested my proposal to the project lead, Trevor, and he called it the "Nuclear Option" in his presentation which he presented to the executives at Make-A-Wish. He had put it as the last option in the slide deck as he didn't know if the executives would like it.

When I came into work the next day, I had a few executives stop by my desk and tell me great work...I was surprised since they had never done that before.

Soon I came to find out that Trevor presented the "nuclear option" and they liked it the most. Couple weeks later, it was implemented.

That year, I remember seeing Make-A-Wish running a marketing campaign around donating points. They had depleted all of their points for the year, reducing their waste to $0. They did so while getting more points donated, which in turn allowed more wishes to be granted.

That was one of my proudest moments.

My calling

I don't think I would have stuck to this path if it wasn't my calling. I keep hearing and feeling this calling. It is calling me to build something great, to change how the industry works, and to apply my skills to an industry that is jaded and lacks vision. To think bigger.