Team GeekWire has been sucking in some of the entrepreneurial advice today at Startup Day, listening to speakers such as Redfin CEO Glenn Kelman, Optify CEO Brian Goffman, Squidoo co-founder Megan Casey and many others share pearls of wisdom about what it’s like to build a startup.

But we took a little time out from the 20-minute talks to interview some of the entrepreneurs in the crowd, asking two very blunt questions: “What’s the biggest hurdle you face as an entrepreneur?”

And: Why did you decide to take the startup plunge?

Here’s what some of the entrepreneurs had to had to say. Are you really surprised?

Farren West, 36,, Seattle:


Biggest hurdle you face: “I’d say finding mentors to walk me through the process so I skip a lot of the hurdles. That’s the biggest thing I am looking for right now. I’ve done some areas of this, but I’ve never done product development from a digital product standpoint… So, I am looking for mentors to help me understand what I am getting in to and how I don’t run really fast in the wrong direction.”

Why take the plunge:  “You own your own destiny, soup to nuts, man. You control your own life. I think that is the most important thing you get out of being a startup or entrepreneur of any sort. You get to decide when you fail or succeed, and how far and how fast you want to go. Whereas, if you work with a big company you can be knocked offline pretty quickly and be fired or downgraded pretty quick.”

Madhu Singh, 28, Roti Roll, Seattle:


Biggest hurdle you face: “Finding the resources to gather the data I need to put the plan together. In the food truck industry, it is not so vibrant where you could go online and get the data of how much it costs to get a truck and retrofit it. Especially since I am trying to use lean concepts and theories to build the truck, to try to find a consultant or somebody who even knows those models first of all and then retrofit a truck accordingly.”

Why take the plunge: “When you wish that something is out there, you can’t just wait around for other people to do it. I want these to be available to me because I want it.”

Ben Dehghan, 34, SpurOn, Seattle:


Biggest hurdle you face: “The biggest challenge, surprisingly is, the gut-wrenching sickness that you get always that you don’t know if you are right. And you have to live with that for a long time until you actually are proven. The way I deal with that is that I have a very supporting wife and very supporting team right now, and we are all working very happily together. But that never goes away in a startup. You can figure out the product. You can figure out the team. You can figure out all of that. But the feeling that you are in a startup and you are flying without a safety net…. that is the biggest difference.”

Why take the plunge: “It was to exactly get that feeling. Because there was no risk before. And without the risk, it is like: ‘Why do people go skydiving?’ It’s because they want to live dangerously and that makes you feel alive…. It feels great. It feels invigorating. It feels dangerous. I feel alive, and I feel young. Everything you’ve imagined you wanted to feel as living on the edge, it is exactly that.”

Ronald Huiskamp, 42, RelocationOnline, Kirkland:


Biggest hurdle you face: “The big dilemma is always the same: Money. I am self-funding this. So, I am taking that risk. I am willing to take it, but that’s really the only hurdle I see. All other things I can overcome. It is getting to where you have a product and you have income coming in to bridge that gap. Giving up the income and sticking your own savings into the business — so burning on two sides — that is the biggest hurdle to get started.”

Why take the plunge: “This has been something that has been nagging at me for probably 10 years. In fact, I moved to this area from Amsterdam with this idea about the land of opportunity and land of entrepreneurialism. (I) had a massive detour and ended up getting a job in this industry that I now have 10 years of experience in. It is a personal drive in just wanting to do that, and wanting to try it and see if I can do it. Also, it is not waiting until I am in my 50s and I am like: ‘Shit, I didn’t do it and now it is too late.’ And having 10 years of experience in the industry and seeing how things can be done better, and just wanting to build that.”

Ruben Gamez, 35, Bidsketch, Spokane:


Biggest hurdle you face: “Time. Managing time. Right now, I have one product, but I am actually considering launching another product. Thinking about whether it is going to hurt the product I have now, because I have a limited amount of time and whether I should be doing it at all.”

Why take the plunge: “I wanted to be fully in control. I had a job, but whenever you have a job you have to answer to other people. I wanted to build something that I was fully in control over.”

Peter Chen, 21, eBerri, Seattle:


Biggest hurdle you face: “It is not really gaining traction, but more so retaining traction. The moment you get users to have them keep coming to your product and monetizing that.”

Why take the plunge: “It was just motivation to do my own thing. I got job offers at Google and for me that just didn’t make sense…. I think it is just the rush. The fact that you can a change and influence that change is a big factor.”

You can see the live broadcast and some of the past talks from Startup Day here. Thanks to everyone for the advice and insights. I learned a lot.

And, if I didn’t get a chance to interview you today, please feel free to share your thoughts in the comment thread below.

Editor’s note: GeekWire is a media sponsor of Startup Day. 

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  • Janism

    I was in the advisory room meeting entrepreneurs in 15 minute time slices. I am amazed by what we were able to accomplish in these brief meetings. I am struck by the lack of customer facing skills and how to think about the revenue model (and eyeballs do not necessarily mean revenue!). In several of the meetings I could think of complete pivots for their businesses that seemed to be real revenue opportunities. The technology founders MUST find business advisors or a business oriented cofounder. The ONE TEAM I met where there was a sales/bus dev guy and an engineer came across so differently than the other entrepreneurs because they could see the whole picture. I would highly encourage anyone from Start-up Day going to the 114 Seattle LinkedIn site….it is other entrepreneurs and serial founders willing to meet for coffee or lunch and support your efforts in moving your business along 1 coffee at a time. Network like mad–you NEVER KNOW where the one investor or first customer might come from. I made a set of angel intros to a dear friend of mine and it led to $250K investment and one of those investors brought in an investor in their previous company and lo and behold that investor wants to take the rest of their round. It took me 15 minutes to make those email intros! You gota find these connection points as they are out there!

    • Anonymous

      what is 114 Seattle LinkedIn site?

    • Anonymous

      what is 114 Seattle LinkedIn site?

    • Conrad

      Another way to think about this is a startup requires many diverse skills and it is impossible for a single founder to have all of them.  I was fortunate in a company I founded in Canada and sold to Microsoft in 2005 to have a partners with very complimentary skills.  I was the tech guy and my partner had incredible business and sales skills.  We built the company on that foundation.  Its important to know early where your gaps are and find mentors or maybe partners.  As someone getting back into the startup world I thought this was a great event overall.  Well done to the organizers and speakers.

  • Farren

    John…great chatting with you at Startup Day. As always you’re working your magic ;-)
    The conference was great and to have Eric Ries some up the day with a scientific approach to running/launching a business was fantastic! Highly recommend attending this event and the Seattle Startup Weekend (Edu in late Sept or Nov 11th) you’ll quickly learn what’s it like to be in and operate a startup!

  • Kenson Goo

    Awesome tips. I am looking for ways to gain traction for my project, and I came across these tips. Now, I have regain my motivation to push my project further.

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