Dan Stroud is all about optics. The TV marketer and producer started his side gig as a headshot photographer after taking dozens of his friends’ and coworkers’ pictures, and realizing they were all offering him money for a reason. When a coworker told Dan that she would be leaving to work at Thumbtack, her parting gift was the suggestion that he set up an account. Not only did Dan follow through and create a thriving photography business on Thumbtack—he estimates that he wins one in four jobs on average—he also joined as a member of the customer acquisitions team in Thumbtack’s San Francisco office. We sat down with Dan to discuss what life’s like now that he works both on and for Thumbtack.
1. How long have you been working as a photographer?
I’ve been doing photography for years now. I started taking headshots a couple years ago for friends and coworkers, and then people started wanting to pay me for my work.
2. How did you end up on Thumbtack?
I heard about Thumbtack two years ago from Olivia (Borsje), who I was working with at the time at Dropbox. When she told me that she was going to be working at Thumbtack she pitched me on it and I decided to sign up as a pro. At the time, I was just figuring out that I could do photography on the side and people would pay me for it. Joining Thumbtack forced me to pursue it as a side hustle in a more serious way.
I started quoting right away. I remember reading advice on the pro center and I decided to lower my prices for the first few jobs. I only charged $100 for my first couple of gigs and then started upping my prices.
3. When did you start working for Thumbtack?
I started working at Thumbtack in August 2016. I remember that while I was interviewing, I got a message from a job I had quoted on telling me in two long paragraphs how great my portfolio was and explaining why they wouldn’t be going with my work. It was this unwarrantedly kind message and it stuck with because of how unusual it seemed at the time.
I realize in retrospect that the message was from Jonathan. I’m almost 100 percent sure of it.
4. Do you think being a Top Pro prepared you to work for Thumbtack?
I think I knew a lot more about the company’s business model than the average candidate because I came in as a paying user. From the start, I had a lot of empathy for our pros because I had been (and am still) in their shoes. When I started I spent a lot of time talking to people about how the product works and had a lot of suggestions from my own experience. Being a part of it now, seeing how much the product has changed and improved makes me really happy.
5. How is your Thumbtack business today?
I do pretty well these days. My hire rate is around 25 percent, so the amount of jobs I take on depends a lot on how much I quote. Very few days go by that I don’t quote. I probably spend close to $200 a month on Thumbtack and get an average of six gigs a month. But it varies—two weeks ago I had six gigs in one week.
I’ve gotten pretty specific about where and how I work. For the most part, I only shoot outside and I have a couple of areas of SoMa that I always come back to. I only quote on projects that are near me and I only do headshots and portraits. Flexibility is important—I shoot between 8 and 9 in the morning or after 5pm.
6. Ever thought of moving into other categories on Thumbtack?
I do some light photo editing work now and I’ve thought about expanding into video editing as well. Video editing is a very different process though and it’s much harder to measure your time in advance. And one day I want to try my hand at interior painting. I find projects like that really relaxing and meditative.
7. Do you encourage your friends to join Thumbtack?
I talk about Thumbtack all the time. When people hire me I always ask how they found out about Thumbtack and I pitch them on other services they can use it for. I think that will become more of an incentive moving ahead; having pros tell customers about all of the other offerings on Thumbtack and referring them.
8. Have you picked up any pro tips since you started working at Thumbtack?
I think that there is still a lot I can do to improve my success on Thumbtack to be honest. I’ve started to automate a lot of my process.
I’ve learned to look for whether someone has hired off of Thumbtack before. It’s an easy way to find people who are just shopping for price, and generally when you see those they only have one or two other quotes.
9. Do you have a favorite Thumbtack story?
One cool thing about being a photographer is that it forces you to walk into totally new situations with total strangers and find ways to make them feel comfortable. You meet all types of people in the process: introverts, extroverts, the occasional CEO.
I remember that one woman I was doing a shoot with very casually mentioned something about her boss, “Mr. Schwab.” I realized halfway through that she was Charles Schwab’s chief of staff.
My first job on Thumbtack was with an investment banker in the city. He took me up to the roof of his apartment and we had this sweeping view of the city below. I just looked around and thought, this is pretty cool.
10. What’s one thing you’ve learned working both on and at Thumbtack?
I’ve realized how real this thing that we’re doing is. If one day I wanted to leave a corporate job and make a living working for myself, I could do it. We talk a lot about the future of work and empowering our pros here—it’s pretty cool to be a part of it.
[Photos via Dan Stroud]