Chris Sacca’s Advice to Founders: Become the Best Storytellers

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quiet when i write, loud when i sing. making tech more humane through writing ❤ peruvian ✈️ l sf l proud trojan.
Sep 25, 2015

Chris Sacca’s Advice to Founders: Become the Best Storytellers

What I learned from meeting Uber & Instagram’s earliest investor

by Silvia Li (@lisamsilvia)

A man of ethics and full of charisma, Chris (@sacca) is the founder of Lowercase Capital and has undoubtedly one of the best tech portfolios. His appetite for risk and his ability to identify amazing founders has led to his successful investment in companies that you know very well: Uber, Twitter, Instagram, and Kickstarter.

Jack Dorsey.Twitter — left, Travis Kalanick.Uber — middle, Kevin Systrom. Instagram — right.

But things weren’t always rainbows and butterflies for him. In 1998, Chris took his loans to build a startup and a hedge fund, and within a week, he not only lost it all, but had a $4 million debt at the age of 25. Five years after, he was back on track and learned that “you will never feel richer than when you are worth exactly $0.”

On September 23rd, JibJab Studios in Marina del Rey, CA hosted a live podcast with Chris and Jefferson Graham from USA Today, donating all money charged to Charity Water.

Here are the 4 main takeaways:

1) For founders

  • Become the best storytellers: Sell yourself, sell your product to the press, sell your vision to investors, employees and most importantly, to your customers. Coming from a lawyer dad and a comedian brother, Chris knows how to tell a story; it’s in his blood.
“Storytelling is at the cornerstone of everything we do: raising money, hiring, press” — Chris Sacca
  • What sets apart great founders — they don’t use conditional language: the founders that he has invested in use future language when they talk about their product. Chris narrated Instagram’s early days when Kevin Systrom coded everything by himself and pitched his plan of action when Instagram would have 50 million users. He received so many NOs from the start-up community, but Sacca smelled and felt the hustle, the product, and the value.
  • Know your numbers, competitors REALLY REALLY WELL: know every single direct or indirect competitor of your product. There’s nobody out there that you actually fear. Know exactly what you are going to do when Amazon comes into the space directly up against you and don’t feel threatened. Travis never doubted that Uber would revolutionize transportation.

“Know how compelling that users love your product and why that is and why users tell other users they love it.”

  • Make investors feel FOMO: valuations are made up; it’s a confidence game at first. There’s so much psychology behind it. FOMO is the enemy of every investor; they don’t want to miss the next Slack, Uber and Airbnb.

2) About Twitter’s CEO

The event started by Graham asking why the board hasn’t chosen a new CEO. “The board is stuck; it’s a broken situation with a broken board,” said Chris. Not surprisingly, he agreed that Jack Dorsey should stay as CEO.

“I think we know how this should end up. This should end up with Jack, the inventor, the founder, the former CEO running the company. I have no doubt he can run it while he runs Square. He is right now and he’s kicking ass at both.”

Getting the founders back involved would be the right thing to do and keeping them in the company is essential, says Chris. Around December, Dick Costolo, former Twitter CEO, let the board know his resignation and the board, after almost 10 months has opened itself to liability.

As a huge fan and user of Twitter, this is really sad to see. But Chris believes that he will get what he wants at the end.

3) For early investors

  • Be proud of every deal you make: Chris has a great sense of integrity and ethics and mentioned that this is the #1 rule that Matt, his only partner, and him share. Have the ability to go to sleep well every night and make the right decisions.
  • Give yourself an opportunity to be rich: his net worth of $1.2 billion according to Forbes didn’t become from his first investment; he tried, failed and learned from those failures many times.

4) About Diversity

  • I asked, how did your experience studying in Ecuador affected the way you see the world? Did that influence the way you invest in companies?
“The thing that impacts the most is hiring…people who have never lived or studied abroad have a limited worldview that makes them feel so uncomfortable to change and entitled to their status.”

Sacca recalls that people at Google complained for trivial things about Microsoft; they would get mad and depressed. He was disappointed to see the lack of empathy of his colleagues since while we get to enjoy the AC in a hot summer day, people in developing countries don’t have clean water, toilet, and food.

“I won’t work with anyone that has not had a shitty job at some point.” — Chris Sacca

The key point that he made is that living there made him more human and help him deeply understand the human condition. This is probably one of the reasons why he is constantly contributing to Charity Water. Humility and empathy are so important to any founder that wants to build an app for 100 million users because your customers come different gender, religion and socio-economic backgrounds.

You can listen to the Q&A and my question starting minute 33:25.

Part I

Chris also recalls the importance of women in VC, tech and startups. He once had a summer intern who now is a VC at Greycroft and asked her to bring him one interesting company that year. Guess what? She brought him Pinterest and he passed on that investment which cost him millions of dollars, just because he didn’t listen to that diverse perspective.

Part II —

Bonus: tips from Sacca from his live talks and blogs

  • Don’t suit up to pitch to him, be yourself, be weird.
  • Success is optimizing for happiness. Happy people create, happy people get what they want, happy people are contagious. Making a lot of money tends to turn people into jerks.
  • Be present — Take a moment to realize what’s happening around you: the smile of your loved ones, the laughs of your friends or the sound of the rain. Things happen so quickly that we set goals for the future while forgetting to reflect on our current state. Set back, think about how you can change every day to be better and more fulfilling.
  • Helping people is the easiest way to get a job. Helping others is hot right now. It demonstrates initiative, dedication, drive, humility and entrepreneurial spirit.
  • Always and always keep your integrity.
  • Why does Chris live in L.A.? Because it’s easier to raise kids.
  • Apparently his daughters record TED Talks on Periscope to motivate Twitter and Uber employees.

For more: you can watch a graduation speech he gave >> here.

That’s me.

Thank you for taking your time to read this long post. I thought I would write and share all my thoughts.

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    Silvia Li Sam

    quiet when i write, loud when i sing. making tech more humane through writing ❤ peruvian ✈️ l sf l proud trojan.

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    Learning about myself, you, and the world through writing. I like puppies and good design.

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