• Startup & Investor Resources
  • Recent Posts
  • Search
  • Contact Me

Instigator Blog

Lean Analytics, startups, angel investing, product management and more!

A Crash Course In Startup Assumptions and Lessons Learned

June 26, 2007 by Ben Yoskovitz

Whether your startup succeeds or fails you’re bound to learn a ton. If you don’t learn a ton, you did something wrong (unless you sold the company for millions and millions, and then who am I to argue with that, right?)

The guys at Xobni, a San Francisco-based startup, published some great lessons learned from their startup experience. More than lessons learned, they list some of their original assumptions and the actual reality of what took place.

Startup Assumptions Are Way Off

Each of the items they list under “what we thought” is an absolute gem. Thank goodness people are blogging more and more about this stuff, because lots of first-time entrepreneurs are bound to make the same mistakes. Experience teaches us so much. In fact, people with past failures have a higher chance of succeeding versus first timers.

I wanted to highlight three of their points:

  1. “We’d launch our first product in two months.” After 13 months, Xobni’s only in private alpha. As Matt Brezina (author of the blog post, co-Founder of Xobni) points out, the idea behind Xobni has grown immensely.

    This point resonates strongly with me, because the Standout Jobs team wants to launch in the Fall. If I’m not mistaken, we have 81 days to launch. Two or three months is not a long time to launch anything, and it leaves very little room for error. We’ll iterate quickly, review quickly and do as much as we can in parallel. But if you spend even 1 week heading in the wrong direction, it’s hard to get back on track.

  2. “The hardest solutions create the most value.” Matt writes, “Graduate school teaches you to find complex solutions to challenging problems. Users teach you otherwise.”

    I never attended graduate school, but I’m all-too-familiar with complex solutions and how easily and often people push them. Users do like easy-to-use systems, but very often they love features too. “Feature-rich” is still something people cling to, even in the Web 2.0 world (although less so.) Keeping things simple, avoiding feature bloat, and making sure your system is easy and fun to use is critical.

  3. “We would spend a month or two raising money.” It took Xobni 5 months to raise their Series A. That doesn’t surprise me. In our case, we were very lucky to raise our money in less time than that, but we were aware that it typically takes 4-6 months.

Many Important Startup Lessons Learned

Many of the lessons learned for Xobni are absolute classics. They’ll hit startups time and time again. What struck me when reading Matt’s thoughts however, is his focus on some smaller startup issues that few people talk about with enough frequency.

For example, in lessons learned #6, Matt points out that looking for deals on small items (phones, computers, food) isn’t worth it; your time is too expensive and precious. Startup founders tend to do everything, and there’s a lot to do right at the beginning. Much of that work is “operational” in nature, or “busy work” — setup an office, get bank accounts, sign thousands upon thousands of agreements and contracts, etc. Being able to outsource that work or hire someone to help you is a huge bonus. This leads to point #7 for Matt, which espouses the value of office administrators and assistants.

Finally, the last lesson learned is perhaps the most critical:

Hiring the best is difficult. We’ll do whatever it takes to get a good employee: $1,200 last-minute flights, $3,000 referral bonuses, flowers for significant others etc. I suppose the enormity of this challenge is evident in the commissions charged by recruiters. They charge 20% of a hire’s first year’s salary as their fee. It is worth it. Your team is all you’ve got.

Well…we all know how I feel about that one, right?

Kudos to Xobni for putting it out there and helping others along the way.

Filed Under: Startups

Want more content like this?

Signup for free and you'll get new content as soon as it's available. Thanks!

Ben Yoskovitz

Founding Partner at Highline Beta, a hybrid venture studio and VC firm that works with large, ambitious companies to identify new areas of opportunity through internal and external innovation.

Previously I was VP Product at VarageSale and GoInstant (acq. $CRM), and Founding Partner at Year One Labs.

Angel investments include: Breather, Spoiler Alert, SendWithUs and others.

My bio »

Buy Lean Analytics

Lean Analytics

"Lean Analytics is the missing piece of Lean Startup!" - Dan Martell, founder Clarity

Get the book at leananalyticsbook.com

Get updates

I've moved to Focused Chaos a newsletter focused on startups, investing and more. Please visit there to subscribe and get weekly content.

  • Startup & Investor Resources
  • Recent Posts
  • Search
  • Contact Me
Views expressed here are mine and mine alone.

Copyright © 2025 · Built on the Genesis Framework