In an address to Rice University students on September 12, 1962, President John F. Kennedy said, "We choose to go to the moon in this decade and do the other things, not because they are easy, but because they are hard, because that goal will serve to organize and measure the best of our energies and skills, because that challenge is one that we are willing to accept, one we are unwilling to postpone, and one which we intend to win."
I wish I had gotten into software with that aspirational vision. I didn’t. I got into it because I thought it would be easy.
I can't count how many people have told me, "Oh, I started building something like this but then got distracted by my day job." The graveyard of half-built real estate tech is vast and growing. Everyone—worst of all, me—thinks building software will be easy. But it's not. It's hard. So, so hard.
Some things off the top of my head:
Everything Takes Longer: I can brute force an Excel spreadsheet to be done no matter what by the end of the day. I can’t do that with software. The knock on effects are endless.
The Hidden Infrastructure: That simple calculator I envisioned automating prepays? It needs a Product Owner to translate my wants to an Engineer to build it who needs another Engineer to test it before passing it to a more formal QA tester who passes it back to the original Product Owner who then passes it to a DevOps team to deploy it up through multiple environments and then everyone needs to go test the existing code to ensure nothing broke. Suddenly, my "prepay calculator" requires entirely new roles I've never heard of before.
Invisible Costs: Our AWS bill has tripled in the last three years as we've grown.
It's Never Actually Done: When I finish a feature, the requests for enhancements start rolling in. "It would be great if it also did this..." or "What if we added that..." Even when building for yourself, the first version will never be perfect, and you'll find yourself in a perpetual chase for improvements.
Security is a Full Time Job: Every single day requires constant monitoring by a team that specializes in security. Want SOC2 compliance? That'll be years of work and six figures, please.
Technology Evolution: We wrote v1 in JavaScript because it’s ideal for rapid development and an iterative approach. About two years ago, we started switching to C# for a far more robust and scalable codebase that can run millions of calculations quickly. Now we have to manage both tech stacks as well as the challenges of them integrating with each other.
Performance: As we've grown, our page loading time slowed down. Excel doesn’t do that, so that was a new concept to me. I’m obsessed with speed, so we have to pull Product and Engineering away from new features to optimize performance. Every improvement comes at the cost of something else not getting built.
Bugs: I always thought software would be like Excel—build it correctly once, use it forever. Wrong. Bugs are a fact of tech life, and all the time spent fixing them distracts from something else.
Support: Even if I was only building for my own companies, my internal team has become “customers” who need support. I can't just build it and walk away - I need an infrastructure to support their needs.
The benefits are amazing. Maybe not as cool as going to the moon, but pretty awesome. Seeing the entire portfolio at a glance. Get a loan provision with the click of a button. Lender adjusted DSCR calculations are completely automated. Get notifications about anything you can imagine. Know what a projected prepay penalty is at any given moment.
But it was brutal getting to that point. Know that "We should build our own software" is the tech equivalent of, "I'll just renovate the property and increase rents." You'd never make that assumption in real estate, don’t do it in tech.
The companies winning with technology aren't the ones who think it's easy. They're the ones who know it would be hard and invest anyway “because that goal will serve to organize and measure the best of our energies and skills, because that challenge is one that we are willing to accept, one we are unwilling to postpone, and one which we intend to win."
Go into it with eyes wide open. Don’t be me…or you might end up getting a similar gift from teammates:
