I polled a bunch of start-up entrepreneurs about their biggest stresses in preparation for my talk at the Northwest Entrepreneur Forum. I decided to post all the feedback here on the blog of curiosity. Thanks to all of the contributors for the feedback. Hopefully none of these highly appreciated contributor entrepreneurs will mind
Enjoy.
“The biggest challenge to me was fully appreciating the amount of inertia that exists in the general consumer marketplace. You need to be much, much better than what’s currently out there to really gain traction in today’s commercial web.”
Mike Davidson, Newsvine
“The realization that you need a network of support and giving into it and the realization that if you don’t show up on a given day, ready to go-little or nothing will happen.”
Charlotte Pruitt, French Fifty
“I had fallen victim to the naïve notion that our idea was unique and that being unique is what made it valuable. With each new competitor I would focus more on what they were doing than what I was doing and stress about how to differentiate vs just executing…”
Ian Blaine, thePlatform
“What is difficult (for me), and unexpected by many new entrepreneurs, is the psychological impact of having to leave things undone, not doings one’s very best work, and having to compromise on almost everything.”
Ryan Petty, Vice President Siemens, Myrio
“No matter how well you think you’ve thought things through in advance, you will get something - probably something important - wrong. Actually admitting you were wrong, and letting go of an idea or belief you’ve been living with during the initial period of building your company is often one of the hardest, but most important, lessons to learn as an entrepreneur.”
Andrew Olson, thePlatform
“I asked someone to move across the country, take their kids out of school and I hoped they would still have a job in 6 months”
Adrian Hanauer, Owner Major League Soccer Team
“The biggest stress, by a significant margin, was the responsibility of maintaining an “always available” service for customers.”
Peter Cooper, FeedDigest
“Investors had already put in millions and the business plan wasn’t working. We had to build a new company on the fly.”
Matt Hulett, mPire/WidgetBucks
Growing the business while still keeping the “vibe” the way you want it is a constant challenge. It took lot’s of staff turnover to find the right people”
Dean Graziano, Visible Technologies
“When I first started mylackey.com I thought hiring people would be the easiest part, I guess I was partly right but learned pretty quickly that hiring people is easy but hiring the right people is very difficult and keep you up at night.. People are the most import asset you have when you’re in a start up environment. Hire smart, not fast.”
Brian McGarvey, myLackey, ZenZui
“I never realized how important my presence and attitude would be at SEOmoz. When I felt depressed or struggled through tough times, everyone noticed and everyone took it harshly. Once I realized this, I was able to put on a tough face at the office and project confidence, but it’s something I wish I would have known at the outset - it cost us a lot of unnecessary anxiousness and concern.”
Rand Fishkin, SEOmoz
“Needing to raise the $$$ so your employees can have food & shelter…”
Michael Dougherty, Redfin
“The initial responsibility of all the families you effect as a CEO. How many grocery bills, mortgages, cleaning services, etc. do I end up effecting which in turn impacts family dynamics if the stress and
responsibility feelings get passed on to my employees?“
Janis Machala, Paladin Partners
“The pressure to perform and not lose money for my friends, family, and spouse who invested and bet on me.”
Janis Machala, Paladin Partners
“The realization that your employees depended on that paycheck
every two weeks and you did too! The fact that I took seed money from family and friends and they may never get that money back.”
Mika Salmi, President MTV, Founder Atom Films
Have your own comments you’d like to add to this as a start-up founder? Please send it to me and I’ll add it to the list!








Hey Kelly,
I really enjoyed your collection of stresses for start-up entrepreneurs — felt like a glimpse into my recent past, and daily thought cycle!
Three things that I’ve spent a lot of cycles on:
1) Are we setting up our culture for success over the long-term? Are we working long-enough hours, but not at too much of a sprint mode, which is likely unsustainable over the long-term? Have we nurtured and maintained a collaborative environment where people know they have input in all areas, but also have ownership over their areas? Do we have a Product Development process in place that provides adequate visibility for everyone about schedules, features, and goals?
2) How to balance the tradeoffs between “money now” vs. “money later”, and the varying trade-offs over terms?
3) Several folks on your list have stated this, but it’s always the monster in the room — constantly stressing over our untested assumptions and maintaining transparency for investors/friends/employees, who trusted us with their financial and emotional investments.
Onward!
Dave