What My Real Estate Agent Taught Me About Running An Indie Software Company

Running a business is tough. There are endless variables that go into creating something that makes any profit: Is it innovative enough; how do you get people to notice and spread the word; how do you keep improving in the middle of cut-throat competition? How do successful business owners get through this?

What My Real Estate Agent Taught Me About Running An Indie Software Company
[Image: Flickr user woodleywonderworks]

Frank Mitrick is a real estate agent in Chicago, Illinois. He and his wife, Cheryl, opened up their company, Real Tek Realty, 30+ years ago.


When someone’s been successfully running a business for more than 30 years, and has my own loyalty as a customer for over 13 of them, you’ve got my attention.

Frank took me (and the woman who’d become my wife) looking for possible locations to purchase our first home. I remember walking into a place and Frank getting a phone call from his daughter about borrowing a car for her high school dance. Years later his daughter was at my dining room table, now a partner of her father’s, helping us negotiate the sale of our home.

We’ve spent considerable time with this family of entrepreneurs. Here are just a few of the things they do to excel in a difficult industry, which I’ve applied to my own businesses like Draft.

Out-Teach the Competition

Those who teach stand the best chance of getting people to become passionate. And those with the most passionate users don’t need an ad campaign when they’ve got user evangelists doing what evangelists do… talking about their passion. —Kathy Sierra

My wife and I had been renting for over three years together. We both had decent jobs and it seemed like it was a good idea to invest some of our money in real estate. But we’re frugal. So we wanted to buy something inexpensive that we could still enjoy living in before remodeling and eventually selling.

When we met Frank, he did what you’d expect most real estate agents would do. He took us around looking at different places, giving us info about up-and-coming neighborhoods and buildings. But as Frank got to know us, and learned what we wanted from our home and investment, he took the education up another notch.


Frank taught us what he would do if he were us. He explained how he buys older properties to fix up and re-sell. For hours he drove us around, no longer looking at things for us to buy, but at properties he owns in different phases of his process to teach us item by item how we could do this too: what type of appliances buyers want; what neighborhoods work best for him–even what ceiling light fixtures he buys.

Frank got our business. Then, we followed his education, remodeled our place, and sold it years later for a profit in a real estate market that was well underway in its disintegration.

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With Draft, my latest business venture to help people write better, the only marketing I’ve ever done is teaching. I blog, do webcasts, answer questions on Reddit, and write lengthy email replies to anyone who asks me for help running their own business–all so I can teach my audience to become better writers, entrepreneurs, and creatives. And my students repay me with helping spread the word like crazy about Draft.

Offer Complementary Services

Imagine a movie theater with a babysitting service. –Kim, W. Chan; Renee Mauborgne. Blue Ocean Strategy

Most businesses struggle to grow, while they fight within a narrow definition of their industry. But as the book Blue Ocean Strategy teaches, you can swim away from the cut-throat competition (the bloody “red ocean”) by imagining how your business can become unique with complementary features and services. For example, Kinepolis is a movie theater chain that started offering childcare services–a move that filled their cinemas with parents eager for a date night.

Being a real estate agent is one of the reddest of oceans. So Frank does what this cinema did. He studied the entire process of home ownership, investing, and re-selling. He’s made himself unique by becoming an entire package of other helpful services. When you’re his client, he comes with the expected recommendations real estate agents have, for example a mortgage broker and real estate attorney. But again, Frank takes it up another level.


Frank has a construction guy, a cabinet guy, a granite guy, and every other guy and gal who could help us invest and remodel our home. He was a one-stop location for complementary services.

Writing software is a also a red ocean full of bloody competition. So like Frank, I’ve studied the process of writing–of which actual writing is just a fractional part: copy-editing, publishing to Twitter and 3rd party blogs, website analytics, productivity, and improving our craft. I’ve built complementary tools and services for everything along this entire chain.

I’ve created a one-stop shop to solve a writer’s problems, making my solution stand out, not amongst the competition, but away from it.

Don’t Just Use Your Product, Need It

Almost all bad product decisions start with people in a conference room saying “sure, that sounds good.” Road to hell is paved with apathy. –Garry Tan, Partner at Y Combinator

When I was building my first business, Inkling, I quickly noticed that the lousiest parts of our product and the things that kept breaking were the things I’d build for other people that “sounded like good ideas.” Our best stuff was the stuff we built because we needed to use it ourselves.

Frank is his best client. He’s out there doing exactly the same things he’s advising others to do. He’s buying property in the same locations at the same prices. And he fixes them up the same way he advises everyone else. All his recommendations for people and services are the same ones he himself uses every day. You’re getting his best stuff, because it’s the same stuff he needs for himself.


I live and die with this principle in Draft–I’m it’s heaviest user. I’ve already written 1,400 words in Draft this morning and it’s only 10 a.m. I can’t let it suck, or my day of writing would be miserable.


It’s incomprehensible that only a small percentage of us decide to follow up once we’ve met someone new. I can’t say this strongly enough: When you meet someone with whom you want to establish a relationship, take the extra little step to ensure you won’t be lost in their mental attic. –Keith Ferrazzi, Never Eat Alone

Every few months we get a newsletter from Frank teaching us more about the real estate industry and how we can take better care of our home. Every Christmas we get a card and a small gift. If my LinkedIn profile changes, he’s the first one offering me congratulations on the news.

Frank knows I have a million things going on, and gently makes sure he has a relationship with me, even if I’m not in the market for anything.

When I was working on figuring out what my business before Draft was going to become, I needed to talk with a lot of potential customers. I’d send out cold and warm emails, and get little back. But I started following up with folks making sure we still had contact, and while I was once worried I’d come across as a pest, now I was told things like, “I’m so glad you followed up. I had meant to get back to you, but things just got in the way.”

With Draft, I’ve made it a habit to follow up with people. If someone says something nice on Twitter, I’m there thanking them and trying to hear more about their experiences. If someone signs up, they get a note with more of my contact info in case they need anything.


Still, observing how well Frank does this reveals how much better I can be. Maybe I should be organizing the people I meet in a CRM tool like Highrise. Maybe I should be scheduling regular alerts to remind me to meet up with new and old friends. Maybe I should remember to thank the people I met with at a recent conference for their conversations.

There’s a lot more I can improve.

Those are just a few things I’ve picked up watching Frank and his family successfully run their own business for so many years.

Who are some of your business heroes? What are you learning from them? I’d love to hear your stories on Twitter: here.