Sumo Cast 001 - Will Bunker






Todays guest is Will Bunker. Will founded popular dating site One & Only which was acquired in 1999 by Ticketmaster and later became part of

"My life is a startup – learn, do & build. 

Startup order: 
#1 family
#2 GrowthX and SV Growth Syndicate
#3 our community"

Traction speaks louder than words. Since building the dating site that became in the 90s, Will has bootstrapped several startups to profitability. He's worked with countless entrepreneurs to help them scale their business. With GrowthX, he is looking to mentor great early stage ideas and the next great entrepreneurs. 

See 2RedBeans, Cargo Chief and Sprig as example investments. 

Don't let his slow southern drawl fool you, Will is a fast thinker - especially when numbers are involved. 

1:53        Will has a fascinating analogy of how Investing can be compared to putting a feeder into a random collection of birds in a birdcage. He describes how investing success is as random as a pellet occasionally dropping from a feeder into the cage, and it is impossible to attribute it to any one thing and repeat it - it is random.

3:27        Will attributes his amazing success and fame to the fact that the startup that he was involved with became an internationally recognized brand.

4:33        Anyone who’s started an internet business can relate that the most terrifying noise is an entrepreneurs silence. Will relates the story of how he started out and how he had to convince people to consider the bizarre concept of online advertising. He tells the story of how AOL lost all his data by physically dropping and smashing the server with his database on it, and the challenges that arose keeping the business going.

8:03        Yahoo entered the market by doing personal ads which proved a challenge to Will and his team. He tells the story of competing a subscription model against Yahoo’s completely free personal ads. Disgruntled clients and abuse became part and parcel of the development of, and Wills unique method of dealing with them.

11:36        The biggest hurdle Will had was who in their right mind would put all their information on the internet on a dating site. He enticed the initial clients in by offering free T-Shirts that he still hasn’t sent out this day, but the clients didn’t care because loneliness is a huge motivator. It taught Will a valuable lesson - is a startup fulfilling a role that people need so bad that they don’t really care about the quality of your startup - they just need you to provide the solution for them.

13:17        Will tells the story of the initial acquisition of He details how the late 90’s interest in the internet as the ‘hot’ property meant that investment was not as difficult to attain as it might otherwise have been.

14:53        A background in industrial engineering meant that Will was well equipped to build a culture of measuring everything that he could to try to be more efficient. Pre-Google analytics, Match’s system was highly advanced for its time giving in depth detail ahead of its time.

17:13        Post, Will enjoyed a couple of years break helping with family project startups before moving into a series of his own startups before finally arriving in a situation where he became an investor to help other people with their own unique good ideas. He’s now invested in over 150 different companies.

19:19        Will always puts himself in a position where he assumes people always have a good idea and asks the question ‘How can I be helpful’ to establish exactly what role he can play in startups development. The example of ‘Uber’ and how many people passed on investing before they got going eventually is discussed.

21:05        Growth X, Will’s new project focussing on the gulf between incubating a new product and getting venture capital into invest in the product. The gap generally revolves around sales and marketing, and Growth X works on helping companies bridge this gap.

24:35        Will has learned that you can’t skip steps, you have to build a learning machine to  establish where your processes are not as great as they should be, and work on a system to fix that and to see the virtual funnel of a business from top to bottom to see exactly where these failings might be.

25:45        Startups are supposed to be a learning machine, and lots of people forget that and presume that their current perception of how their company should run is 100% correct when in reality its probably close to 0%.

27:38        Will uses flashcards to learn and retain information, breaking questions down into chunks on flashcards, of which he now has 45,000 cards. He makes the point that its amazing how goodwill you can inspire from a founder if you know a little bit about their background - and this is just one of the things he learns from his flashcards.
30:25        He didn’t know how to program at the age of 25, and learned different programming languages at the rate of 20 different commands a day over a reasonable amount of time to become proficient in these languages.

31:28        Will would write ‘Most Progress / Least Effort’ on a board and stack rank all the current tasks to establish which project would make the biggest payoff with the least effort to work out which projects to pursue on a given day. He also describes offsetting large tasks with limited payoff over time. 

34:00        Favorite Growth Hack - taking all your value props and turning them into Facebook ads and measuring which value prop gets the greatest click through.

34:30        Favorite Startup - to take an 18 wheelers and change them into drones that can be driven remotely.

35:22        Tips for a startup approaching an investor include knowing what the investor is interested in - learning if investors are or are not interested in and moving on accordingly.

35:55       Recommended book - Anything out of the Lean Startup camp.

36:18        Recommended book for personal life - anything out of the Tony Robbins camp.

36:48       Favorite Technology - drones and their uses going forward, also the falling price of electricity means that new opportunities will be available to operate so much cheaper. Also Satellites will become much more prominent going forward, where nothing will go unrecorded anymore.