🏕️ Michael FitzGerald. A novelist turned CEO and what it takes to have a startup in Montana.
Rad Dad, hosted by Kirill Zubovsky
Michael FitzGerald is the CEO of Submittable.com, a Missoula based company that helps businesses to accept, review, and make decisions on applications and documents, all in one place. They are like Dropbox with a purpose, and their clients include Nike, NPR, Knight Foundation, Stanford University, Playboy, National Geographic, the New Yorker and thousands of other enterprise brands we all know and love.
Liberal arts student by training, Michael had a career in writing, but inspired by a fellow Montanian, he chose to follow a path of entrepreneurship. It has not been easy and it has taken a long time to get right, but Submittable is growing, scaling, and kicking butt.
The day after raising their Series A funding, Michael found out that he had a terminal cancer and he was supposed to be dead in six months. Fortunately, thanks to the advancements in medicine and a whole bunch of awesome friends, he was able to get treatment and is here with us today.
Today Michael joins us on Rad Dad to talk about startups, the good old 90s, what it takes to write a novel, what it’s like to be dealing with a serious health condition while being the CEO, and how all of that shapes you as a person to lead a worry-free life with the kids and the family.
In this episode
- 00:06 - Who is Michael FitzGerald?
- 00:57 - Where did Michael FitzGerald get his start in software?
- 04:38 - How expensive was San Francisco during the first Dot-Com?
- 05:42 - Are there any similarities between the first dot-com crash and startups now?
- 08:54 - How did Michael FitzGerald end up in Missoula?
- 12:04 - The ultimate startup - how can you make money from something worth nothing?
- 18:18 - Who are some other successful Montana entrepreneurs?
- 18:59 - How entrepreneurial is Montana?
- 22:35 - What are the advantages of running a company from Missoula, MT ?
- 24:42 - What did ghost-writing teach Michael?
- 27:20 - What does it take to publish a novel?
- 32:12 - Does being the CEO change your life?
- 35:10 - Is it a good idea to start a company when you have young kids at home?
- 37:25 - What is the story of Paul Graham trying to talk Michael FitzGerald out of starting Submittable?
- 42:08 - Is it true that startups never get easier?
- 43:46 - What are some challenges with growing employee count?
- 44:22 - What's the story about Michael FitzGerald getting sick with cancer?
- 46:46 - Why is metastasized cancer so dangerous?
- 48:37 - How do you tell your investors about a terminal illness?
- 50:22 - What role did Y Combinator play in curing Michael from cancer?
- 52:46 - How much does it cost to cure cancer?
- 55:34 - How much should a CEO get paid?
- 56:39 - Do thoughts and prayers cure cancer?
- 57:45 - How can you help someone who has cancer?
- 01:00:40 - What is the hardest part about getting cancer ?
- 01:02:50 - What should people do with their life?
Smash Notes summary for this episode
Who is Michael FitzGerald?
Michael is the CEO of Submittable, a company that powers submissions and applications around the world.
Where did Michael FitzGerald get his start in software?
Michael first started his career a copywriter, in San Francisco in the 90s, during the first dot-com wave. It was a crazy time that originated a lot of ideas that are finally coming to fruition right now.
Money was plentiful and ambitions were grand. You could have no idea of what you were doing, and still great a great sounding title at one of the hot software companies.
Fairly quickly into his gig, FitzGerald realized this was not a great job for him. He wanted to be a novelist, not spend his time endlessly playing with words. HTML skills in hand, he became an "online producer" for PC World.
How expensive was San Francisco during the first Dot-Com?
San Francisco was "too expensive" in the 90s. Michael was paying about $650 for a Studio apartment in the Mission. It was a lot, given his salary was about $3,200 a month.
Are there any similarities between the first dot-com crash and startups now?
The first crash and what we are going through today does not sound alike. Amazing things are being built right now with a lot more utility than companies that were selling and going public in the 90s. When you are in the bubble though, it does not feel crazy. That said, San Francisco DNA of a beautiful hippy city is gone.
How did Michael FitzGerald end up in Missoula?
Michael has always wanted to be a writer, but there were not many entry level jobs for a novelist. When his girlfriend, now wife, got into a writing program in Missoula, he followed along.
This wasn't his first trip to Montana. When he was a little kid, Michael's family came there to look for a job, but after about a week, his mom requested they move back to civilization.
It was now a perfect time to spend some time in Missoula again!
The ultimate startup - how can you make money from something worth nothing?
After moving to Missoula, FitzGerald went to work for Clutchmasters. It was a company stated by a high-school dropout who figured out how to get free clutches, remanufacture and sell them at a massive markup. For FitzGerald, this was a great lesson in how to turn a simple idea into a profitable company.
Who are some other successful Montana entrepreneurs?
Dennis Washington is a well known persona, a high school dropout who started with nothing and became a multi-billionaire by generating leverage.
How entrepreneurial is Montana?
Montana and small-town America are ridiculously entrepreneurial. In a small town, there are no regular jobs. It used to be that everyone was either working in a small business or hustling 2-3 jobs to pay the bills.
Unlike the Silicon Valley though, Montana companies are not trying to eat the world, they just want to create awesome products and create jobs so their own kids don't leave Montana for other places.
What are the advantages of running a company from Missoula, MT ?
Due to lower costs, better quality of living, and availability of willing talent, companies are able to hire fair-priced employees, which enables them to price products differently. Where a Silicon Valley company has to sell $50,000 products to pay their bills, a MT company is able to sell for $5,000 and still turn a profit. Everybody wins.
What did ghost-writing teach Michael?
By writing books for executives in top software companies Michael was able to get a front seat in whatever business they were in and to learn, while getting paid for it.
What does it take to publish a novel?
For three years he would write in the morning, go to his job, edit at night, and do it all over again until 400+ pages were ready. Then, it was time to sell the novel, which was a really challenging thing if you did not know how to sell.
Michael FitzGerald wrote a novel called Radian Days only to realize that writing novels did not really pay.
Does being the CEO change your life?
Michael feels he is a very lucky person. He's been able to do what he wanted to do. He has a great family, and they are not starving. He gets to walk to work. He is pretty happy, and if it was not for stage-four colon cancer, life would be amazing.
Is it a good idea to start a company when you have young kids at home?
FitzGerald started Submittable when his kids were 3 and 5, and in hindsight it was a silly idea. Starting a company takes all of your energy, so your kids don't get to see you very much, and when they do see you, your mind is often wondering somewhere else, focused on problems at work.
What is the story of Paul Graham trying to talk Michael FitzGerald out of starting Submittable?
During Y Combinator, Paul Graham saw a picture of Michael and kids and wanted to make sure that Michael really wanted to do a startup, and to inflict the underlying stress on his family.
FitzGerald said that he was going to build a company, take it back to Montana, and hire 500 people so his own kids would have a place to work, and therefore be able to work and live in Montana.
So far, Michael FitzGerald is keeping with his promise.
Is it true that startups never get easier?
Both. It gets easier for a while, until you hit the next set of challenges and then it gets hard again.
What are some challenges with growing employee count?
Adding 10 more people does not make your company 10x faster, and in some cases it makes it slower, for a while. It's normal, but you have to anticipate it.
What's the story about Michael FitzGerald getting sick with cancer?
One day Michael felt sick, went to see his doctor, and got scheduled for a colonoscopy. Missoula being a rural place, the procedure was three months out. Michael forgot about it and went on with the business, raising money for his Series A.
The day after the deal closed, he got called to the doctor. Feeling stoked about money in the bank and the prospects of a greater future, FitzGerald went to the hospital, only to hear some awful news. His prognosis was death.
"If you get the answer that you don't want, you go find another answer!"
Why is metastasized cancer so dangerous?
Metastasized colon cancer gets into your organs, liver first, and liver is the hardest to treat. The whole point of your liver is to remove toxins, and when you start to blast the body with chemo (toxins), the liver gets overloaded.
The solution, which saved Michael's life, is a slow-drip chemo, delivered by a HAI pump, attached to a patient's liver.
How do you tell your investors about a terminal illness?
If you get great investors, True Ventures in this case, they will back you 100% regardless of challenges and circumstances.
What role did Y Combinator play in curing Michael from cancer?
When Michael found out that he got sick, he posted a message on the internal Y Combinator board asking for suggestions. It turned out, founders were eager to offer to help. Some were doctors with knowledge of the disease, some were founders going through a serious illness, and of course, there were even startups working to cure cancer.
How much does it cost to cure cancer?
A typical scenario for a cancer patient, they first go broke trying to cure the disease, and then they die. Most people cannot afford stage four cancer.
How much should a CEO get paid?
This particular CEO is getting paid less than some of his employees, putting all his money and energy into the company, banking on the future success for all.
Do thoughts and prayers cure cancer?
It might help people who believe it works, but there are also a lot of tangible things you could do to actually help a cancer patient.
How can you help someone who has cancer?
First, don't ask what you can help with. That simply puts the burden of creating and scheduling work onto the sick person and their family. Instead, just do. Bring food, mow their lawn, rake some leafs. The best you can do is show up, do it, and leave without asking for attention.
What is the hardest part about getting cancer ?
When you are sick, the hardest part is lack of control. Chemo is basically poison for your body, and every two weeks you have to poison yourself. Life starts to swing from times where you are feeling low on energy and unable to do anything, and times when you are desperately trying to catch up, before you are down again.