Founder Hits & Misses from Ariel Poler, one truly Bad Ass Advisor

Ariel Poler

Ariel Poler, a friend, world-class kitesurfer and experienced technologist who is now obsessed with what he calls human augmentation, has been a bad ass advisor for decades (with Strava, StumbleUpon, Thumbtack, Freedom Financial among others).

He takes an all-in approach, has a waiting list of firms seeking his counsel and is particularly thoughtful. He recently gave a keynote at the recent Vator Splash event in Oakland and shared his speech with us. It’s so damn incredibly on point that we wanted to share it across our Bad Ass Advisors network, which I started last year to connect bad ass advisors with bad ass companies in the health and tech fields.

Companies’ Ariel advises and has invested in

Hit: Focus on direction & execution over speed

  • Speed is overrated!
  • What good is going fast in the wrong direction?
  • The better you understand where you need to go, the faster you can move
  • Move fast to determine the right direction! Then get your execution right and step on it…
  • But, never stand still!

Hit: Take Risks. One at at time!

  • Make big bold bets. All of the most successful entrepreneurs do!
  • Diversify over time: focusing on one thing at a time. Don’t “hedge your bets”.
  • But, it is OK to experiment with different things for a while until you decide what you want to focus on. Just for a while…

Hit: Buy Yourself Time

  • Always have plenty of runway — do round extensions if necessary (and viable)
  • If you can’t raise more money, cut your burn. The earlier you do it, the less painful it will be

Hit: Control the timing of your financing’s

  • Once you have one term sheet, even a crappy one, you have leverage
  • Three weeks or three months? Same outcome. Give investors a deadline! I’ve seen deals done in a week
  • If you don’t have a term sheet, try to create some other forcing function
  • Avoid a permanent state of fundraising. Focus on the business and fundraise when you are ready

Hit: Know how to ask for help

  • We have a very supportive culture in Silicon Valley.
  • We focus on relationships rather than transactions.
  • But, to get help, you must do your homework:
  • Determine the right people to talk to
  • The appropriate topics you want to discuss
  • Help us help you…
  • Be Specific
  • Add value

Miss: Trying to follow all the advice you get

  • Silicon Valley is very diverse and there are many philosophies and approaches that co-exist here
  • Context is key
  • You must find the approach that works for you
  • Customize learnings to your situation

Miss: Believing everything you read in blogs and books

  • Most success stories are made with 20/20 revisionist hindsight
  • It often takes time, e.g. StumbleUpon and Twitter were not overnight successes as some people think…
  • Hindsight gives great strategic vision. In most cases, successes are built incrementally.

Miss: Fast to hire, slow to fire

  • The moment you start thinking someone might not be working out, they aren’t
  • But letting someone go is difficult and painful for everyone, so don’t cut corners when hiring.
  • Same goes for co-founders, service providers, and others.
  • Prioritize talent Over experience
  • Do thorough references!!! Or better yet, a trial period.

Miss: Focusing on the pitch rather than the investor

  • It is all about investor fit
  • Think about dating… Who cares about the restaurant choice if there is no chemistry
  • Don’t chase the metrics or the checkboxes
  • And, don’t get greedy

Miss: trying to solve investors excuses

Most investors do deals when they get excited. But they don’t like to say “I am not excited”, so instead they use an easy excuses, such as:

- You are too early

- The deal is too small

- I want to see more customers/revenues/technology

Be careful about trying to “solve” their excuses, because once you do, they are likely to find others. Instead, figure out how to get them excited. Or, better yet, focus on the business.

Investors like to keep their options open.

Good luck.

Ariel is actually one of our featured Bad Ass Advisors on our home page

Go Ariel!

10-time entrepreneur and Chairman of UCSF Health Hub and VC at Series A BuildersVC. To date made over 150 private investments in health, enterprise….

10-time entrepreneur and Chairman of UCSF Health Hub and VC at Series A BuildersVC. To date made over 150 private investments in health, enterprise….