This interview is with Dana Underwood, co-founder of The Muse Factory, an Innovation Endeavors startup that helps people “crowdsource” gift-giving to create super-personalized gift experiences. (Download the audio recording of this interview.)

Q. Tell us about your background. 

A. Sure. I’m 37, which I can’t believe. I went to college in mechanical engineering at Northwestern. I then went straight to grad school, and came out to Stanford to do a Master’s in mechanical engineering, and built robots which was a lot of fun. Then I worked at a startup in New York that was an RFID company. And then I jumped into bio-tech for a while when I moved out to the West Coast. And I did some product design as well before going back to business school. I got my MBA at Stanford, and then I went back to bio-tech in a sales and marketing role. And then finally I started my own company. Somewhere in there, I also became a professional photographer.

Q. Tell us how your career path has taken you to where you are today.

A. I had always wanted to go to grad school; that was a no-brainer for me. I thought I want to be a professor, so when I moved out to Silicon Valley for grad school back in the late 90s, there was so much going on. I really wanted to be part of that excitement — I remember talking to people at Netscape who wanted me to do some consulting for them my first week at Stanford. It was an excitement I had never seen in the Midwest coming out of Northwestern.

I moved to New York after my Master’s. This was the beginning of a theme for me. One thing I love to be is a fish out of water in all but one way. The way New York fit into that was that I was working at an 11-person startup two blocks from Wall Street, wearing shorts and t-shirts to work, but working in this geographic area where the financial sector was on the forefront of what everyone was thinking about. Yet I was at a startup, and I loved being in that place but not immersed in what was going on all around me.

The reason I left the company — and this is another theme — was because I didn’t think the leadership was strong. I told them that in my exit interview: I didn’t want to be part of a company that treated its employees the way they did. Throughout my career, there have been times when people have run companies in ways I would never want to run my own company. And only now, when I am running my own company, do I have the chance to reflect on those things and ask myself the hard questions about how I would handle the situations they were in, which is always a great reminder.

When I moved back west to be an engineer in bio-tech, and then later ended up at a three-person product design firm, it was the dot-com crash at the turn of 2000, and the market had just tanked in Silicon Valley. After the crash, I remember when I used to commute from Mountain View to South San Francisco, and traffic just got so much better! It was amazing the impact it all had.

I decided to go to business school because I wanted to be in a position to at least impact the decision that companies were making, if not make those decisions on my own. And I wanted to be able to understand business in a way that would help me contribute to the strategy a company was employing, and how they might actually go about doing things, as opposed to just being the execution person, the person at the lab bench, the person who was soldering or building a circuit board.

After business school, I was in bio-tech at Genentech for a while. I did sales, market planning, and then I ended up leading sales operations for one of their drugs, which was just fantastic training. But I also knew I didn’t want to get too comfortable. It was at a point where I thought, “OK, Genentech is great, and I’m doing really well, but in a year it’s going to be really hard to leave. And I’m a startup guy. I want to be somewhere where I know my contribution and the contribution of my co-workers is obvious, and there’s no dead weight.”

I knew I wanted to go back to smaller companies. So I actually chose to leave, and it was on the best of circumstances I could have imagined. I joined as the fourth person — the first employee after the founders — a photography technology startup called Lytro. This was an opportunity to fuse my passion in photography, which I discovered in business school, my technical background, and my business background. I believe their technology is going to change photography. Ren, the founder, is brilliant technically; he’s great with the community and with fundraisers. But we had very, very different styles. So I didn’t stay there long.

When I was younger, I would have endured that for longer. But as I aged, I realized that I had seen the writing on the wall in previous situations, and I wanted to make sure I didn’t stay in a situation where I knew I wouldn’t be happy.

So I left. I took a year off. And in that year, I became a professional photographer. I chose to feed that passion 100 percent. I did a photo shoot with the President in that year. That was really encouraging in terms of me trying to make a living at it. And then I returned to the workforce because I realized I didn’t want to stay a full-time photographer. There’s something about me that needs technical stimulation. Even if I had been a full-time photographer, I’d probably be working on some technical solution on the side for photographers.

I joined Pacific Biosciences as a product manager, where I worked on the product development of a large DNA sequencing machine. And after two and a half years there, Runway came up, and it was an opportunity to join a program with the support and the resources to start my own company. It was a hard decision to actually take the leap, and it wouldn’t have happened if it hadn’t been for how Runway was structured and the timing of the opportunity.

Q. Tell us what Runway was. 

A. Runway is a program that was run out of Innovation Endeavors, which is a venture capital firm that is financially backed by Eric Schmidt from Google. Runway was one of their alternative funding models, where they took a bunch of people with entrepreneurial aspirations, vetted them, brought them together as strangers, and then had them self-select into teams. And they pitched themselves as teams to the fund, and the ones selected to be in the Runway program got 6-9 months of support — financial, mentorship, and network introductions.

So it gave you a platform to think about what business you want to build, to explore different markets, test ideas with users, and get out on the street and ask questions so that you have a strong foundation on which to build your business.

Q. What were the specific steps for how you made your most difficult career transition?

A. I’ll talk about the transition out of Genentech. I went to Genentech in an MBA rotation program. The program was fledgling at the time; it was the brainchild of one of the VPs there, who saw some promise in me and hired me into the program. I rotated pretty quickly and got some roles that would have normally been given to more senior members of the sales force. I was in a great position, a position of influence within that brand.

So the decision to leave was met with a lot of, like, “What are you thinking? Why would you ever leave Genentech?” People asked me that. And one of the things I do from time to time is re-read my Stanford business school essays. I used those essays as a cathartic opportunity to really be as honest as possible about what I wanted. I wrote about wanting to start my own company, at a time when it was such a remote possibility in my mind that it was less scary to write about it. But it was honestly what I wanted.

So I remember re-reading those essays and thinking, okay, if I stay here at Genentech and my lifestyle continues to change with the amount of money I’m making — to this day, Genentech is still the place where I made the most money in my career — then it’s going to be harder and harder for me to leave. I didn’t grow up with a ton of money; my parents were middle class and worked for the government, so they gave me everything I needed but at Genentech I was on the way to having more money than I thought I would ever have. And I thought that would be hard for me to back away from.

So part of the reason I left Genentech was that I knew that getting back to a startup was the thing that would feed me professionally and capture my interest most thoroughly. There was a lot of risk associated with the financial aspects of doing that, building my own thing, going back to startups. But I care so much more about how it feels to work, than what I’m working on. I need to wake up and want to go to work, and want to spend time with the people I’m working with. And I’ve come to the point of view that the money will somehow follow — and if it doesn’t, and I have to work until the day I drop dead, I need to enjoy it every day, and I need to have fun doing it.

So that’s where I am now.

Q. By the way, what was it like to photograph the President during your year as a professional photographer? 

A. That was fun. That was the gig that made me think, “Gosh, I need to charge for this.” I never charged for photography before that shoot. And I didn’t charge the campaign either — he was campaigning at the time. He had done an event at the Fairmont in San Francisco and I think he raised $14 million that night, which at the time was a record.

And I got a chance to shoot him with two other people; there six or seven of us in the room. And I remember sweating through my dress shirt and my blazer, and  he came into the room and he was fantastic — my expectation of every national-level politician is that they’ll be charismatic beyond any measure the rest of us can achieve. And he was fantastic, and he came up and we talked for a couple minutes.

For me, because I’m African American, on so many levels, it was an incredible experience for me to just be there, not only to witness history, but to be part of it. And one thing I didn’t do is ask him for a picture with me; I think I rationalized the fact that I felt like it would be imposing by saying, “Well, there are tons of people who have pictures with the President, but how many people can say they were hired to take pictures of the President?” (Laughter)

It was one of those huge moments. And the power of exposure for me ties back to the career stuff we’ve been talking about. I went to a fancy all-boys school in Baltimore, and there weren’t that many kids that looked like me. But Ben Carson, who is the chief of pediatric neurosurgery at Johns Hopkins, is an African American man, and he was right down the street in Baltimore, and he came to speak at my school. And I can’t say enough about the power of example; Ben Carson’s example, when I was 10 or 11, was the first moment when I thought, “I could do absolutely anything.”

And almost like a bookend, meeting Barack Obama while he was campaigning, and then later seeing him go on to win the Presidency — and I went to the inauguration and saw him take the oath of office — was another one of those powerful, powerful examples for me. It was extremely influential in terms of my becoming a professional photographer but also in my life in general.

Q. Tell us what it’s like working on your own company now. What do you do day-to-day? 

A. I think I heard about how much work it would be — and it is a ton of work. But for me, it’s a labor of love in a couple ways. I love being able to be self-directed. I love being able to structure my time in a way that works for me. Those play a huge part in my happiness.

I pretty much work all the time; I do four things in life at this point. I work on my company, I work on my relationship with my girlfriend, I exercise, and I take pictures from time to time, although that’s taken a bit of a backseat. And being able structure those things and put them in places that work for me is one of the great benefits of working on my own company.

I have a co-founder, Tony Deifell, and he’s fantastic. One of the most important things that happened for my company The Muse Factory is that Tony and I came together. That’s important because there is nothing more vital than the ability to communicate with my co-founder. Openly, I need to be able to tell him when he’s pissing me off, when he’s doing something awesome, and when there are other things going on in my life outside of work that are impacting my mood. Because he needs to understand the full picture. Having a co-founder is like having another spouse. I have to think about the things I say and how I say them. I have to be very in tune with his perspective. And doing those things makes us a better team for sure.

Day-to-day, well, let’s take today as an example. I’ve been up since 8:30 a.m. working on letters to investors. We’re reaching out to potential investors, potential employees, which is a process I’m managing, and we’ve also built a community of people who are supporting us. So today is a day where I’m thinking about our outreach.

Tony is brilliant at building movements. He has 22,000 Twitter followers. He knows how to actually get support because he worked in the non-profit sector, which is so valuable at this stage of our company for inspiring people with a vision, and getting people to do stuff where there may not be as much financial incentive as there may be in the future.

So today I’m working on that. But tomorrow, I’m going to be working on something else, like a pitch deck. And the next day, I’m going to actually work on refining our product. Taking feedback we’ve gotten from UI people and potential users and refining the actual product we’re building.

So you have to wear every single hat. And the memories of my work life in the past come rushing to the forefront based on what I’m working on. Good management situations, bad management situations, things I’ve done wrong in the past. I made a mistake last week, for instance, sending an e-mail before we had a conversation with someone, and it might impact a relationship that Tony has with someone. So I’ve got to think about that, and figure out how to not let that happen again in the future.

Q. What is Muse Factory and what are you guys building? 

A. Muse Factory is the company I co-founded with Tony last fall, and what we’re building is a social gift-giving construct — or framework.

We did six months of research into gift-giving. So we understand the emotions, the psychology, and the commerce behind gift-giving. In fact, when we talk to investors, they are always pretty impressed with, not only how much time we spent researching, but our depth of knowledge around it. And that’s a direct benefit of having been in the Runway program.

So we’re building a social giving framework that allows me to get a gift for you by crowdsourcing the creativity of our common friends.

Q. So it takes the notion “it’s not the gift but the thought that counts” to a whole new level. 

A. That’s exactly right. What we learned was that, when people say it’s the thought that counts, it’s sort of a mitigating comment. It’s meant to offset a gift that didn’t land in exactly the right place, or the fact that someone didn’t get you a gift. But every time someone doesn’t execute on a thought is a missed opportunity. So what we’re trying to do, at a high level, is inspire thoughtfulness.

Q. If you could change one thing about your career path, what would it be? 

A. When I think about the entire arc of my career, there is probably only one thing I would change.

I like the fact that it’s taken me the amount of time, the number of experiences, that it has to get to this point. Because, as older entrepreneurs, I think Tony and I have a professional maturity, and I think that just comes with time, and having had both great and really terrible experiences at work.

But the thing I would change is that, when I left Lytro, I definitely burned bridges. And I do not like burning bridges. I happen to have been in a bit of a self-preservation mode at that point, but I wish I hadn’t burned that bridge.

I learned there is a difference between reacting to something and responding to something. And I reacted in that situation. I would go back and try to sit and think of a response. The outcome probably would have been the same eventually, but the way I handled it might have been different.

In terms of my current startup, the one thing I would change is to remove my personal financial concerns from my efforts to build this company. It is a reality of being an entrepreneur that you have to make certain sacrifices, and I’m in the throes of that. I just want to make sure that my decision making around how to build a company is never impacted by any person limitations I have. That’s important because I have a co-founder, and because the judgment you exercise can be different depending on how you let your emotions or your limitations guide you.

Q. What was the biggest lesson you learned at Lytro, and what do you wish you could have told your younger self if possible? 

A. Great question. I think I would have told my younger self that the decision you’re making right now, and the way you’re about to handle it, reflects on the last few weeks or couple of months. But the impact of that decision is going to be much longer than that, whether it’s good or bad.

I would have reminded myself of how I handled previous bad situations. I would have tried to channel some of what I did in my first job in New York, and how I handled that situation. Because I think we all have access to our better selves when we are going through hard times. And we have access to moments when we’ve displayed our better selves. It’s just hard sometimes to reach out and bring them to your present circumstances.

So I wish I’d had 37-year-old me, saying, “Okay, I hear you. I understand how you’re feeling, and it makes sense to me, but think about the time you went through this other thing. And then think about projecting how you’re going to behave forward five or ten years.”

Q. Where do you see yourself in the future and how is what you’re doing today going to help you toward that goal? 

A. I want to wake up in the morning, open my eyes, and decide what I want to do that day. That is my long-term goal. It boils down to freedom and independence for me.

It took me a while to get to the point where I thought freedom and independence can come in the form of running your company to sustain your life. In other words, if I have the autonomy to build something I want to build, but I have to work and I can’t retire, then I need to shape what that looks like.

So I’m working on achieving the long-term goal, which will come with some sort of professional success. But I also know that I want to create a reality where I’m happy in my work well into my retiring years. And that’s all about creating an environment where I’m working with people I want to work with on something I want to be working on.

Q. What advice do you have for people interested in exploring some of the career experiences you’ve had? 

A. Starting your own company is an unconventional choice. And I think preparing yourself mentally for lots of people naysaying or casting doubtful glances as to why you are pursuing it is a way of inoculating yourself against being influenced by those things. Be ready for people to say, “Oh, that’s hard.” Or “Why would you do that?” That’s one thing I would advise for people interested in starting their own businesses.

For people who want to make a transition, there are a lot of ways to get information about who’s done it before. For instance, for my company, we are currently starting to interview potential employees. And I have a good friend who went through a hiring process last year which was a nightmare for her. So I sat down with her and asked, “What exactly happened, and what were you thinking?”

The point is, whether you want to be a trapeze artist, or a photographer, or an entrepreneur — there is always somebody who is closer to it than you are. Try to find those people to understand more about the reality of what it’s like. The only things that get published in popular media are the success stories. And they don’t often focus on the phase I’m in, which is where everything is hard and everything is new. So getting closer to the people who have lived that is a way to explore it before you actually dive in.

Schedule a private FIRE consulting session

Schedule a 1-2 hour session with me to analyze and plan your path to FIRE

Schedule Now