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Character lessons by @Twitter, @Uber, @Instagram, @kickstarter Investor Chris @sacca at #PandoMonthly last night

By Joy A. Kennelly

Last night I was invited to hear Twitter, Uber, Instagram and Kickstarter Investor, Chris Sacca, speak at Pando Monthly by a female entrepreneur I respect and admire online and as a result, really not knowing what to expect, plunked down my $20 for a chance to experience this "fireside chat."

I had no expectations because I don't read Pando Daily and was just introduced to it with little time to research or read before arriving at Zephr's door filled with curiousity and hope. However, my friend has started numerous businesses and is very connected which made me trust her judgment.

I will admit, after hearing all the companies Chris has invested in, which if you're not familiar, are super hot right now in the tech world and elsewhere, coupled with the fact he appeared to be huge fan of Obama via reading his Twitter feed, I kinda expected him to be arrogant, full of himself and annoying, but was pleasantly surprised the opposite was true.

He was thoughtful, humble, generous, revealing, honest, kind, and inspiring.

Chris and sarah6

(Too bad the moderator didn't take a page from his book, but that's another story. We're chalking it up to the fact she's pregnant and probably doesn't realize how bitchy she comes across. Sorry lady, but someone from our gender needs to speak truth. And I'm not just saying this because you said, no questions from the seated audience after I stated mine.:)

Anyway, I was so inspired after hearing him speak for three hours, I felt compelled to share my experience with you. Although, I will admit, I slept on it because some guy called me a poser the other day (to which I responded he was a dick and an ass - good Christian that I am.:) and wondered what people would say when they heard I was privileged to hear one of the richest, smartest, coolest investors in the tech world (in my humble opinion.:)

But after sleeping on it and waking up at 4am buzzing still, I don't care. Think of me what you will because to be honest, I don't write for your opinion. I write for mine. If you're a writer, you know there are times you are compelled to share your thoughts in writing to process it yourself and this is one of those times.

Back to my story.

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When I arrived, I was super early and would have been super lost except for overhearing another guy asking directions too. Jackie was very cool and helpful which I generally find among tech heads. No pretension, just mass knowledge just like my programmer friend Paras.

(Speaking of cool, if you're looking for an interesting, smart company to support, buy from, or invest in, check out Jackie's here: https://thejunglestand.com/JungleStand/)

We traisped through Zephr's offices, which are very hip and sound like an incubator for digital-focused filmmakers, and out into the alley to arrive at their large warehouse space where we were promptly shushed out into the street by the zealous organizer because we were so early.

Hey, what can I say? I was excited!:)

I left briefly and when I returned the alley was filled with eager programmers, startups, entreprenuers and the friend who had originally invited me, Espree. Know her? Cool girl and reminds me a lot of one of my young GA room-mates who works in tech with Oracle whom I admire too.

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In any case, pretty soon the doors opened and we all streamed inside to enjoy pizza and beer (and in my case, Coke) before the interview began.  Jackie had been kind and saved me a seat, but Espree suggested we move to the front and pretty soon, her young skateboard friend, Dante, herself, her other lawyer friend, Damion, and myself were staring at the stage face on for the next three hours. 

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Talk about butt ache!:) But soooo worth it! Chris is amazing! (This is prior to launch during set-up.) 

Now if you don't know Chris Sacca's story, read it here: https://en.wikipedia.org/wiki/Chris_Sacca or here: https://www.apbspeakers.com/speaker/chris-sacca Or just ask around, like I did of Jackie who gave me the Cliff Notes before the evening started. Or Google Chris Sacca. He's all over...

Seek and ye shall find.

But if you can, watch the Pando Monthly video if they share it. Not sure how that works yet, but assume they'll be doing something with the footage and/or interview. Kudos to Sarah Lacy for landing Chris because this is one of the few interviews he has given since moving down to LA part-time. (Yes, he's here! Sound the trumpets! Los Angeles is totally becoming the tech hotbed and I just love it!)

The reason I suggest watching vs. reading is because you will see the essence of who this guy really is without someone else's filter, including mine. He is nothing like I expected and totally someone I feel I could be friends with, he is that down-to-earth, funny, and real.

I also admired his integrity. He may not always have had it growing up a young, brash, arrogant investor when he day traded his student loan money in college, but losing 12 million and ending up 4 million in debt like he did has a way of humbling you. 

What I really liked hearing him say when this happened, was, he "declared I wouldn't declare bankruptcy." And took the next five years working hard to repay all the debt he owed. That impressed me immensely. He said when he paid it all off, "you have no idea how good zero feels."

He shared how he accidentally overpaid his student loans and they sent him a check for, I believe it was, $38, and to this day he says it's pinned on his fridge because he likes seeing they owe him money. lol

I thought it fascinating because Financial Guru, Dave Ramsey, always talks about how the rich don't carry debt and they live debt free. Hearing Chris say it too was only confirmation of what I'd learned in Dave's class. Makes me glad it's one of my top goals to which I'm very close except for my student loan ironically enough.

Chris and sarah

I also liked how Chris refuted the moderator when she accused him of using Goldman Sachs, to which he replied, "No money from Goldman Sachs - you should fact check."

He shared how he started day trading and when it's going great, it's easy to think it's because you're a genius, and when things go bad it's because you're unlucky, but now he's learned it's actually the opposite. When it's going right, that's when you're lucky and when it's going wrong, you're f-ed.

He shared how easy it was to fall into that trap when all his ski buddies were telling him how wonderful he was because they had been able to buy boats and homes investing through him back then, but he realized it's important to have people in your life who will call you on your BS like his wife does now.

For me, it's my parents. lol 

Moving right along.

He shared how he hustled to make money any way he could and was one of the first lawyers on Elance doing odd jobs, even once doing a VO for a famous black athlete in a low, modulated voice similar to that guy's style which cracked me up because Chris is about as white as they come.

He also wrote contracts for porn companies and said he's the only guy to make money in the business without removing his clothes. Chris is just clever with words - a writer's dream which is why I took so many notes cuz I knew I'd want to write about him once he started speaking.

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The moderator, Sarah Lacy, whom I admire for her moderating skills in asking great questions and her deep knowledge, asked him some hard hitting questions which seemed to stop the flow every so often because it seemed antagonistic rather than forward moving. Overall though, great job at moderating on one level.

That said, I'm sure her style is what tech readers love, but meeting her for the first time and hearing it in person for the first time, I was a little put off because I really felt they had a great repoire and he was opening up and sharing stories he admitted at the end he will probably regret the next day, and hearing someone ask him what he thought about negative reviews about himself is enough to make anyone shut up and mistrust the agenda of someone you're speaking to.

I loved hearing Chris reveal how hard his life had been before he made it. If you've been an entreprenuer for any length of time, like I have, you know it's not easy and it was great to hear I wasn't alone in this. Chris really had compassion on those who are struggling in this economy although he doesn't seem to compute that Obama played a part in this and appears to blindly support him, although it was encouraging to hear he invested in Uber which is run by a Libertarian and often has passionate political discussions with him.

My kinda guy.:) Not the Libertarian per se, just anyone who is willing to passionately talk politics and have intelligent discussions not filled with name calling. My style.

Chris even admitted Silicon Valley is a bunch of group thinkers politically and although that was disappointing to hear, at least now I know. Sarah did ask him if he was as disappointed in Obama as many are at the end of the interview and I appreciated her doing that, to which he spewed the party line which I hope young people will research before blindly accepting it because someone they admire said it.

But what do you expect from someone who raised 100 million for Obama and has taken meetings with the President? Maybe I might even think differently about Obama if I had been invited to give my feedback on females in the workplace and in small business at the White House too.

I did, after all, attend the man's inauguration. What?! You didn't know?:) Yes, it's true. I attended Obama's inauguration at the special invite of Rep. Jane Harmon to whom I am very grateful. I consider it one of the highlights of my life to be part of history, especially as one of the lone conservatives in the audience.

Trust me. I was a novelty! lol But enough politics. I have to leave shortly and want to get this out.

Chris and sarah3

Compassion.

I think that's where we left off. When asked about why he kept on going despite incredible odds against him when he first started out, he said "I didn't have a choice." It was in his dna. He said, stories of bouncing back aren't just about titans of business. People fought in wars, have lost their homes and jobs and come back, you just don't hear about them. I admire him for not being prideful about his personal comeback too.

Chris has tremendous empathy for the struggles we all face which endeared me to him because he gets it. Those who have money handed to them and have never faced failure or loss don't understand the depths of despair and self-reflection you go through when all you have is you and God (in my case) and you have to pull yourself back up from rock bottom.

Chris does. That's why my friend and I were so inspired by him. He was empathetic, compassionate, honest and very transparent on how hard it was and how he relates to those who are going through it now. He even acknowledged he knows how much $20 can be for someone when they're bootstrapping because he encountered that when he was flat broke trying to network and he used to sneak in through the kitchen to attend events because he spoke Spanish.:)

When I was younger I read a book of 100 biographies of world famous people and the running theme throughout all was those at the top gave back, they were humble and they treated all people with respect. The most successful companies, churches, institutions, and organizations are also run by these kinds of people I have observed over the years.

Now for those of you who have a company which is doing well and you're starting to receive bids because people want to buy it, here's some advice Chris gave which you might want to listen to:

"If someone offers you money for your company, walk away and think about what really matters. Money - how much do you want? Do you want to continue working in the company and if so, how does that look? Where do you want your company to be based? Who do you want your boss to be? Ask yourself all kinds of questions to allow yourself to really think about what's important to you."

Chris said, armed with that self-awareness, then go back and negotiate on your terms. He said there's no better negotiator than an engineer because they have no filter. They just tell it like it is. I agree, having grown up around so many. That's why we get along - we're both blunt.:)

What I hope every young investor will heed is this next bit of advice too. "Good investors are in the service business." Chris says he gets involved in companies to help and as long as he's helping he sticks around. He probably got more involved with Twitter than they liked at first, but when he was dragged into investing the initial $25,000 he invested, he didn't have that money to lose and wanted them to succeed which is why he was so hands on.

Now, not as much, but he continues to buy Twitter stock because he feels it's the next Google. Interesting, eh? I love smart people.:)

He also said, along those lines, a VC's role is to "empower the entrepreneur" not to be the star and take credit for stuff. It's like when a publicist jumps into every promo shot with their client on the red carpet - I hate that because it's not about the publicist, it should be about the client, just like it's not about the VC either.

Are you listening to us? STOP WITH THE SELF ADULATION.

What I also enjoyed learning is how Chris thinks about Twitter. He says the real value is in the community, the users, and it's created a venue where people communicate. So sparse and simple, it's all about what's not there vs. what it's like on Facebook. Or as Eric Schmidt, whom he quoted regarding Twitter, says, "It's the poor man's email."

Chris, having worked for years at Google, also said, "Twitter is an art problem. Google fails at social because they don't get art." Isn't that interesting? That's why even though Blogger is among the top something of websites, Google has never put money or energy into it. They don't care. They're more about the science than the look.

The part of the evening that really quieted the room, which by the way, was standing room only in a space designed to fit about 500 maybe, correct me if I'm wrong, was when Chris shared how much more people matter than money and holding grudges. You could have heard a pin drop then and also when he said he went from 12 million profit to 4 million in debt over night. 

It's life lessons like these that make powerful people resonate with their audiences. He shared how someone in Silicon Valley had once betrayed his confidence and he held a grudge for years after, even ignoring his emails when that guy wrote to tell him he was going to bike ride cross country like Chris had done in 2009, in essence, "joining his tribe" as Chris so eloquently stated. 

Then recently he learned this same guy was in an accident while riding and did a face plant at 27 mph and is now in a coma. It's made him ask, how meaningful can it be? He may still hold grudges, but it's so shallow. He passionately said, "People matter more than an investment in a company that isn't even around any more."

It was so deep there for a moment, even Chris said, can we get back to talking about the fun stuff. I think it was important for him to share this though because I know so many people who hold grudges, myself included, and I find once I let it go, I'm so much freer. It's just not worth it people. Friendships should always matter more than money.

Or politics for that matter. Get over it. That's me, not Chris saying that part.:)

Some other great words of wisdom Chris shared is don't let you inbox dictate your day. Be on the offense and look at your To Do list before your email. Make what you feel is important, your priority, not what others think is important via their email.

So true.

He also shared how he invites people over to his home for the weekend to get to know them better on a whole other level  since he moved to Truckee and counts many of those people as his closest friends. He moved because he was running out of excuses on why he couldn't go to coffee with people. LOL

He told us he was inviting so many programmers over at one time, it got to be too much and took the money he would have spent on an office and bought the house next door to host them now, calling it Camp LowerCase (lowercase?:) which I thought was brilliant. 

Chris loves helping people and said, he wants to be obsolete by Series B. He's not on any boards, he just helps them get things going and likes to fund opportunistically, under the radar. Now he's focusing on the intersection between tech and media. 

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My alarm is set to go off now telling me it's time to wake up which ends conveniently at the same time I have wrapped up my blog. I hope some of my blog helps you with your startup, your life, and your goals because after hearing Chris, and everything he's accomplished, I believe anything is possible with hard work, dedication, drive, ambition, and focus.

Have a great day! I leave you with this fun shot of the door prize he gave to the person who came the farthest...

 

Oh, this just in, here's the full video:  

 

Comments

Tanisha Carden

Great article!

Joy Kennelly

Thanks Tanisha!:)

Joy

Interesting. The link I posted to his interview was changed to this version. Still cool, but now you're stuck with just interpretation of the event.:) shoulda been there...

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