How To Get Started As A Business Leader

Posted by

Your life and your success is not obvious. It’s not a given. It’s not a direct path.

I often say that the best careers in marketing (specifically the ones that have a digital/new media slant) are very squiggly. They involve everything from stumbling through university and very crappy jobs to bad choices and decisions that were driven by financial debt instead of personal opportunity. Every year, I do my best to attend the TED conference. A couple of years ago, the name Chris Sacca was bandied around as someone who everyone wanted to not only meet, but hang out with. He was (and still is) a venture capitalist with a background at Google (in the early days) and an early investor in companies like Twitter, Facebook, Instagram, Kickstarter and others (you can see what he’s about right here: Lowercase Capital). On one of the nights at TED, we both happened to be on the same shuttle bus (I was shy and didn’t say anything). Later that evening we both sat next to one another at a late night jam-session that was being hosted by one of the hotels (I still didn’t say anything). I didn’t want to look like a fanboy (I was just impressed with everything that he had done at such a young age). People were constantly swarming him. It felt like there was an air desperation in hopes that some of his magic pixie dust might sprinkle over them. It turns out that – shock of all shocks – Chris is a lot like you and I. He’s a normal guy that is just following his dream by trying to help others. He was actually two million dollars in debt not that along ago, but was able to turn his life around. He’s endured crappy jobs growing up, and as a venture capitalist is first to admit that he’s wrong much more frequently than right. His life philosophy and how he thinks about opportunity should be turned into a book. You’ll just want to be a friend’s of Chris. If you don’t want to be his friend, you will be refreshed by his perspective on business.

It’s about your foundation.

Kevin Rose (Digg, Milk, Revision3, etc…) hosts an incredible video podcast called, Foundation, where he has in-depth conversations with, "influential founders, entrepreneurs, and business leaders in the tech community," according to the website. With all of my heavy consumption and infovore mentality, I had not heard about this show until today and somehow stumbled upon this incredible hour-long conversation that Rose did with Chris Sacca from July 2011. I could not stop watching it. Not only is it a fascinating look at Silicon Valley and how relationships are built, it’s an amazing education for everyone in marketing to learn from. They talk about the value of networking and relationships, what success looks like, how business models are created and much, much more (including how Sacca thinks Twitter will not only make money and become a big business, but what this means to marketing today… and moving forward).

Stop what you’re doing and immerse yourself in this world…


  1. OMG Hope the last two minutes doesn’t distract you from your current book writing mission! Really interesting guys. Interesting world. Thanks for sharing.

  2. Thank you for sharing that Joel. That was SO totally worth the hour. I agree with your comment that Chris has an amazing story. Inspires me to go be more “helpful”. 🙂

  3. This was one hour very well spent. I love the flow of this interview from the early days through to Google and the later investor stories. Rose has a perfect interview style where he keeps it chatty but stays on point too in order to cover the nitty gritty. Sacca seems like the kind of guy you could riff with for hours.

  4. I didn’t get “spec work” out of that at all. Spec work usually involves someone asking you to do something for free… Being helpful usually comes from a genuine passion for doing what you love and wanting to share it.

  5. There is no doubt in my mind that Chris’ story is wonderful and inspirational. I also have no doubt that being ‘helpful’ is the right thing to do… the right approach. But I still can’t help but feel, deep down, that we’re wrapping spec work in a ‘helpful’ wrapper. Many of the stories revealed in the video revolved around ‘this guy did this amazing thing for me… I never asked him to, he just did it and I was like wow that’s ‘money'” which started a dialogue or got the guy the job or whatever. Doing unsolicited work, either as a ‘fan’ of a product or service or as a person trying to get an opportunity = spec work for me. Do I ‘help’ people? All the time. Do I expect reward? Sometimes. I’m not trying to ignite an argument about what is considered SPEC work, just giving my impression of the video.

  6. Thanks everyone for the extremely kind words. A couple of points in response to the comments.
    On spec work – I think indeed there is a difference between spec work and just being helpful. Consider the difference between being asked to do something and then doing it for free. Versus, not being asked to do something, but realizing it needs to be done and it will showcase some of your talent/value/passion. Kevin’s own Foundation website was designed by a guy who had actually redesigned it on his own one night without even asking Kevin, and without Kevin asking for anyone to redesign it. The designer just decided it needed a facelift. He sent Kevin his concept and Kevin then hired him to design the page.
    My best interns/associates, are usually people who ping me on Twitter showing me articles I might have missed but should know about, or who call my attention to hot companies I might miss. They never start by begging for a job. Instead, they provide value in my Tweetstream to the point where it isn’t any contest for who will get the job.I haven’t even met the two guys who work for me now. But their Twitter contributions got me comfortable with their value and now that they work for Lowercase, they continue to shred.
    Now, all this said, I have debated spec work with @mike_FTW. I completely agree that many people don’t ascribe enough value to design work. One of the quotes on my business card is “Simplicity is hard to build, easy to use, and hard to charge for. Complexity is easy to build, hard to use, and easy to charge for.” That said, it takes some chops to become awesome. It takes grinding it out. It takes paying some dues. It takes bearing some risks. I have placed enormous bets on instinct and heart alone. If you want oversized outcomes, sometimes you have to break from establish patterns and shed security blankets. Working for free isn’t working for free if you are getting more from it than they are.
    When I started working at Speedera, I didn’t make shit. Literally, they should’ve handed me a pile of shit. I could have burned that to warm my home. Nevertheless, I got behind their door and past the stack of resumes of those who were infinitely more qualified than I was. Within a few months, I was indispensable. Suddenly, I was an executive. I would’ve never made it to that path if I had applied for a regular job and fit into a regular cost center code.
    Same thing at Google. Frankly, I was hired to do a minion’s work there. I was overqualified for my role. But, I took it with sheer confidence that I could lever their platform to be a true player.
    So, I understand the theme of creatives not wanting to be undercut by other creatives who are doing all this work for free. I also encourage everyone to know their own value and fight for it. But, let’s be careful to not judge those people who take sincere advantage of underemployment to irretrievably wedge their foot in the door and make the real shit happen.
    Books – I am definitely not anti-books. I read all the time. I am collaborating on a book with one of my favorite authors in the world right now. There is a bidding war erupting for a book my wife just co-authored/designed. I dig books.
    My point was that for business/startup/social media advice, I am very intimidated by the long time the elapses between submitting that book to the publisher and it appearing on the shelves. I feel like the Internet and my lessons learned move faster than that and I am constantly learning. It is hard for me to put a permanent stake in the ground and say, “This is it. All of it. Period.” I see how much discussion and factchecking and corrections happen on Tim’s site after he publishes each book and it frightens me as to the immovable nature of printed pages.
    Anyway, thanks again for all the good vibes here. Made my day. Probably the next couple of days too.
    — @sacca

  7. There are few people on the planet who intrigue me as much as Chris, it’s hard to put a finger on the *exact* reason why, but he’s one of those folks you meet and just know it would be a hoot to sit around the fireplace and share a beer with.
    But I’d like to tell you a story about Chris to back up this notion of ‘being helpful’. It’s positioned like it’s some strategy, but honestly I think it’s just his nature. What Chris doesn’t know (I don’t think) is that I literally trekked across country once to an event he was speaking at for the sole purpose of putting my face in front of him. Not to talk to him about anything in particular, not because I needed something, but simply to validate whether he truly was the person I thought he was and if so to make myself known and get out of the way.
    Gary V told me Chris would likely show up at the last second so instead of going into the conference I staked out the area around the elevator that led to the room and waited. Sure enough I found Chris in his western shirt and backpack looking around lost and trying to find the conference room in time. I nonchalantly directed him to the elevator like I was on my way there and rode up with him. No introductions, no pressing the flesh, just smalltalk and an elevator ride. After he spent a full half-day on stage I spent 5 minutes with him afterwards. In those 5 minutes of conversation about a non-profit I was donating some time for he directed me to 2 different names of folks I should talk to and would be helpful (unsolicited).
    Since that time he’s offered his help on a couple of occasions that I’ve asked, each time something that benefited neither him nor I but could do some good elsewhere. Including trying to help out a guy with a couple of weeks left to live. These weren’t things involving money, but rather some of his time, which frankly is much more valuable. Keep in mind that Chris probably doesn’t know who the hell I am even now, not really, even after he’s helped me out on a couple of occasions. I think he’s just ‘that guy’, and for that I’m extremely grateful, I would have hated to fly across the country just to find out he’s a polished turd.
    He is what you see, and that’s a pretty rare thing these days.
    Matt Ridings – @techguerilla
    p.s. – Mitch, hopefully we’ll get to tape another show together soon. We had entirely too much fun on the BeanCast not to repeat.

  8. Truly honoured to have you stop by, Chris. I look forward to connecting at TED. I agree with you on the spec work. I’ve often used my skills to wedge my foot in the door… and I still do it to meet new business prospects and build our client-base at Twist Image. Being helpful and adding value first is paramount.

  9. Matt! I love that story. Hyper flattering. I definitely know who you are and love hearing from you on the Tweets. Thanks for the goodness, man.

Comments are closed.