How Being Confused with @Jason Helped Me Launch My Company

Not sure I see the resemblance here…

Jason Calacanis likes to say that he met me in a San Francisco restaurant when someone meeting him for lunch came up to my table and mistook me for him. When the guy asked me if I was Jason, I immediately put two and two together. Funny thing was, I certainly knew the Jason he was referring to and he happened to be sitting at a table not too far away.

What Jason doesn’t know (but he will now) is that I had been studying him for several months, trying to learn everything I could about the startup world. You see, I come from the furniture industry where the word “startup” is not the hot topic of conversation. I have been in this industry for 25 years, running and building my furniture brand TrueModern for the past 7, having never raised any money, and frankly building a reasonable business the old fashioned way. But in the Bay Area, the startup culture is infectious, the technology being created is inspiring, and the startup world intrigued me, given the fact that I was working on an entirely new way to manufacture and sell sofas. I knew that I needed to learn more; I needed a crash course, so to speak. Although I am not sure where or how I stumbled upon Jason’s array of media, I can tell you that I studied it to no end. I poured through the archives of “This Week in Startups” podcasts, listening to each episode and taking notes along the way. There are certainly others out there offering startup advice, but what I liked about Jason’s style was his no-BS way of laying it out. He was essentially making a step-by-step road map for me and all I had to do was take all of the information and link it together in chronological order to get my startup off and running. One of the notes I recalled were guidelines on how to reach out to an investor or mentor. That day I was mistaken for Jason, it just so happened that I had an email partially written to him explaining that I wanted to attend his Launch Scale event, but the $5,000 ticket price was out of my price range. This “mistaken identity” was just what I needed — the perfect segway to introduce myself to Jason. I wrote to him explaining what had happened, who I was, and then finished the email with this:

“So here’s the deal. I am not pitching you for investment, but in fact I want to be a part, in some way, of your Launch Scale event. I think it’s a great event and I am eager to learn more about scale. That being said, your CEOs need cool stuff to sit on. I make great stuff so I thought it might be a good fit. Let me know if I can help you.”

To my amazement, he answered with a “yes” and we were off to the races. I did end up actually meeting him later, and in typical Jason fashion, he started asking me a million questions about my current company and my new startup, which now had a name: BenchMade Modern. I ended up doing the stage furniture for that event. I learned a lot, and while it was more fitting for TrueModern, I still needed more help for my startup.

Reddit founder Steve Huffman (R) sitting in one of our lounge chairs next to Jason (L)

Fast-Forward Two Months: Jason called me into his office to discuss doing the stage furniture for the Launch Festival event. Once again, he started grilling me on where I was with my startup. I recall him asking me to “show him” whatever I had. I was not prepared for this at all. I happened to have a bag with an iPad in it, but when I pulled it out, it was at 1% battery. This is what Jason had talked about: always be prepared for any potential encounter with an investor. Make sure all your devices are fully charged with some sort of backup in case it all crashes. The 1% battery threw me for a total loop, and while I fumbled to connect my laptop to WiFi, I got it together enough to explain where I was with the new company. He thought it looked great, and asked me to not only do the stage furniture for his next event, but also launch my new company on stage (if I could get through his launch prep classes first).

Wow. How was I was going to launch a furniture company, while technology-driven, in a competition all about new tech products? I had no app, so to speak, but what I did have was a sudden urge to win. My competitive nature inspired me, and in the end I would take Jason up on his offer.

I was already behind all my competitors. Most of the launch companies had been accepted into his incubator class and had been preparing for months now. I needed a way to wow these people with a presentation worthy of such a crowd, but had so much to learn. I quickly learned that being part of the “Launch family” gave me the opportunity to learn from other great entrepreneurs, who I never had access to previously. I was invited to sit in on several of the incubator meetings where I got to hear from amazing speakers like Josh Williams, co-founder of Gowalla. I also watched each startup founder present their pitch over and over again as they received critique from Jason and other seasoned entrepreneurs. This became my pitch class, and I learned that I needed a wingman, or “driver” as Jason calls it. Typically this is the co-founder’s job: running the controls as you do the pitch. This needs to be seamless as they navigate through the app, perfectly in sync as the “pitch man” tells the story. This is much harder than it looks, you know. You watch these companies launch up on stage, but what you don’t realize is just how much work it takes to get there.

One Month To Go: My good friend Patrick Whitehouse was up to the challenge of being my driver and wingman through the next month of preparation. Together we went on a crash course plan to not only launch this company, but to win this competition. We attended more incubator sessions and immediately started building a presentation. I practiced that story over and again, trying to get what had become my entire life’s work boiled down to under 5 minutes. I would record it and play it back to myself, fine tuning every little detail. My trick was to rehearse in the car on the way from San Francisco to Redwood City. This was typically an hour commute and I would say it non-stop, again and again and again.

Four weeks before the event is the first big rehearsal in front of top-notch investors where you get critiqued on your presentation and hear advice and questions from investors that have seen a million of these. Our first big practice presentation was at a Sequoia offsite room. I don’t have to tell you the significance of what it means to be presenting in front of Sequoia. Here is how it works: You go up and present in front of the group. It’s very nerve-wracking, but it pushes you to do your best. Next, you get critiqued by your peers, the presentation coach Tyler Crowley, Jason, and guest investors. After your group has presented, Jason likes to get a read from the investors on which company they would hypothetically invest. Lo and behold, the Sequoia investor chose us! That was just the confidence we needed for the next practice session two weeks away.

Our final practice was at Sequoia. I happened to be on a previously arranged RV vacation with my family that week. So I cut the trip a day short and kept the RV so that I could drop my family at home and sleep in the RV as close to Sequoia as possible the night before. I wanted to make sure that I was well rested and that there was no chance I could get caught up in commuter traffic hell. This was a day that everything needed to go perfectly. The history here runs deep at Sequoia and can you feel it the moment you walk in. The company logos that line the wall are big names that we all aspire to be. This is clearly the A-Team, and it showed. Final practice goes like this: as you’re presenting, Jason tries to distract you. He’ll throw a ball towards you or he’ll cut the power to the display monitor — all these distractions are designed to prepare you for something inevitably going wrong during your presentation. It happens to at least one company every year. With all of this intense coaching, we leave feeling ready as ever. Five days until show time.

The Sunday before the event we do a dress rehearsal on site on a big stage with lots of lights, cameras, and huge screens. It’s optional but I cannot imagine declining the opportunity. That was the day that things fell apart for us. We had to be quick on our feet. We had prepared a dual-screen presentation using our own iPad kiosk app that was designed to walk the audience through our in-store experience. The screens were not working together so we basically had to retool the presentation to a previous version. This was a setback — nothing like a curve ball right at the very last second. But thanks to Jason, we had prepared for just this sort of thing.

Launch Day:

Tony Hawk (L), Chris Sacca (M), and Jason (R) sitting on our stage sofas

The big day arrives. It’s our turn. We roll a giant wall of sofas out onto the stage, along with an iPad kiosk all mic’d up and ready to pitch. With such a large stage prop, the judges are trying to get an understanding of what we are up to. Our plan was to show up with the biggest, most badass wall of product they had ever seen. We would wow them with real product. Not just another app in a sea of many, but product that they could really feel and touch.

Mobile wall of sofas

Then we outline the business plan. Our nerves were a bit of a mess considering we were about to present to such a large crowd of investors and industry insiders. I’m sure the fact that we had just called an audible and changed the entire format of our presentation the day before had something to do with it. Endless practice paid off though as I was able to hit my marks and go through my story, just as I had practiced a thousand times over. Check it out here if you have a few minutes.

Looking out from the stage at a sea of attendees

After we finished presenting, the judges hit you with all kinds of questions. Good solid questions mean they understand the business in just a four-minute pitch. For the most part, we got great questions and the judges understood what we were all about. Answering these questions can be a bit tricky without sounding like a know-it-all, a salesman, or worse, like you’re making things up just to appease the judges. We had been coached to just admit it when you didn’t know the answer. A simple reply with, “Great question. I don’t have an answer for that right now. Let me get back to you” works wonders. While you are busy answering the questions, your team is behind you moving your presentation props and materials out to make way for the next company. Jason has a way of moving things along and keeping the crowd focused and off those pocket entertainers we all tend to grab the moment we lose interest.

At the end of each segment, each presenting company is scored by the judges. One by one they are asked for their first, second, and third choices. Talk about nerves. This is the moment. Remember, this is a competition and we’ve come to win, so in our minds, this is the finale. How would we rank against our peers in our segment? Drum roll please… We won! Well, not exactly, but we did outscore everyone in our segment. Of the five judges, two of them scored us as their first place pick. One judge scored us as his second pick, and the other two judges selected us as their third choice. All five judges had us on their scoreboard as their top three. This was quite the moment. I could not have been more proud of my team for what we had accomplished in just a few short months.

In the end, we didn’t win the entire event. A company called Abra took the main prize. Abra is a person-to-person money transfer platform — basically a financial app with a ton of curb appeal. Looking back on it, we really had no chance against an app that was set up to go global right from the get-go. That’s just what the investment world wants these days. But we will take a segment win all the way to the bank, so to speak. It helped us raise our angel round with much success. It gave us a platform from which to speak.

If you ever get an opportunity like this, I highly recommend taking it. It’s not all that often that you get a chance to learn from the A-Team. It was worth every moment.