[S1,E14] “We had a client before we had a product” – How YC alum Pretty Instant pivoted into becoming Uber for photographers

Doug Rogers is a co-founder and Director of Product at Pretty Instant – a service that disrupts the industry of hiring photographers for family and business events. Pretty Instant started as an event photo booth service, then they (kind of by accident) applied to Y Combinator, got approved for the program and narrowed their focus to what they were doing extremely well – matching photographers with events.

How did they actually get clients before really having a product? How do they prevent problems in delivering the service by their photographers? What is the story behind them getting approved to YC? What do investors say to the fact that the company is spread between Silicon Valley and Boston?

Watch the interview and discover insights of Pretty Instant’s story!

A lovely shout out to our partner Runway and to our sponsor UnStock — an on demand community and marketplace for mobile videographers.

Here are some highlights from the interview:

  • For Doug, having a regular paycheck was not something that would drive him in life:

    “I worked there for about 5 years. I had a fancy title and all that, but I wasn’t fighting the good fight. I came home, felt bored and felt like I wasted my time, even though they kept giving me checks.”

  • Doug and his team quickly realized that what they were doing as a side gig may soon become something really big:

    “It was just a huge thing, everybody loved it. People would tap us on a shoulder and ask us how we did it. I remember saying ‘I think we might have something here.’”

  • Going through YC application, as many startup founders say, is great for practicing answers to crucial questions about your startup:

    “Applying to YC, even if you have no intention getting in, is sort of good exercise, because the questions they ask are questions you as a company should be able to answer.”

  • And then you’re facing an exam on how well you know your business:

    “The interview is pretty brutal. They don’t give you a hug at the end or anything. They ask a lot of really good questions that you are bummed you can’t just answer like that.”

  • YC notifies startups if they are approved for the program on the same day of the interview. Doug and his team were far from enjoying themselves while waiting for the news… :

    “After the shortest 10 minutes of your life, there is the longest three hours of your life waiting to find out if you got in. We just hang out in Mountain View, stared at the floor and off at the distance just waiting.”

  • YC often suggests some product modifications or narrowing down the range of their functionality:

    “It was funny. What they actually suggested we do in the interview, we were reluctant to do and then ultimately ended up doing it half way through Y Combinator.”

  • Raising money is a full time job. That’s why while in fund raising mode, CEO should totally devote his/her time to it, while the rest of the team should work hard on the business:

    “While you’re in fund raising mode, you don’t want the rest of the business to grind to a halt. Because while you’re trying to raise funds all your profits are going down, all your numbers are going down, it doesn’t look very good for investment.”

  • I asked if Pretty Instant wants to become as simple in ordering a photographer, as Push for Pizza is for ordering a pizza, and this is what Doug said:

    “We want to be that easy. The thing about pizza is, if pizza sucks, it’s not the end of the world, but if a photographer sucks, that’s a big deal.”


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