Starting Up

Jan 21, 2019 | Sam Rook


Great insights from the tech field

I am a bit late with this post mainly because I needed the time to read this Interesting post by, Jonathan Swanson of Thumbtack. What Thumbtack does is interesting but not important to my point today, just know that it is an app company that has grown to a valuation of over $1 Billion.


What IS interesting are the ideas he talks about through his experience of building Thumbtack from an idea to a viable company. We often equate different industries as having little overlapping characteristics but when you read Swanson, you understand many of these ideas are applicable to nearly all types of business.


My favourite point made by Jonathan is the very first lesson:


That is so d*&n right and it applies to everyone who works to build anything from their own event planning business to a home renovation contracting business to the next darling of the App Store. Success doesn’t come from being confident alone. Success comes from being confident you can do the work yet being humble enough to seek help when you need it. It is doing unpleasant things that seem “beneath you” in the process of growing your idea into something real.


Fred Wilson, a famed Venture Capitalist in the United States shared this fantastic story that really illuminates the power of confidence and humility. It is the story of how his VC Firm completely missed Airbnb when they had a chance to invest.



Here was Fred, one of the best venture investors of all time, admitting he missed one of the best startups of all time. Of course there is another part of the story and it’s the Airbnb side of things. As told by Fred, it is the extreme confidence AND extreme humility that the founders required to carry through the tough times. Imagine doing this to raise funds for your startup company:



That post is from 2011 so we know how Airbnb worked out all these years later. The confidence in their idea and ability to find the right fit for it was key to their eventual success. But so was the ability to swallow some pride and sell generic cereal boxes at a political convention. I doubt anyone that bought one of those Obama O’s or Cap’n McCains remembers buying them. Certainly they would have no idea that a simple box of cereal has turned into the biggest short-term home rental company in the world.


No matter what you do, remember to have confidence in your ability but also humility to find the help you need. You may not turn into a darling of the tech world but I am learning that both traits will make you a success in whatever you do.