Startup Chumps

Well now feels about as good a time as any to punch out another blog post. 40,000 feet about the Pacific Ocean this time, en route to San Francisco, entire family in tow. I’ve been saying this so much it’s well past being trite but it has been a crazy 7 months. Time to reflect on some of the highlights now though. So, since August last year….

We put a 2 year startup project on hold to pick up ScriptRock. We coded up an MVP website. We submitted it (plus a cheesy, in hindsight over the top, Hendrix-backed video) to Startmate.

We got through to the interview stage. We went through the most mentally draining day of our lives on that day, somehow ending up at Club Retro listening to John Farnham at midnight (damn you Bart).

We sweated it out during a week long wait for the results and then lost our shit when we got in.

We ditched our comfortable, well paid jobs and started the program. I lost sleep. We met the other teams, not talking much at first. Heads down, the sense of competition present but not yet the pressure. We met mentors. We got drunk with mentors. We practiced pitching and practiced pitching… and practiced pitching some more.

We simplified our product. We put out an alpha. We got our first feedback.

We incorporated in the US. We got a bank account. We signed a hundred forms. We learned that coding makes a product, not a company. We felt consumed by admin as a result.

Our pitch got better. It was decided that I’d go solo on it. Nice to know I was trusted with it. Scary too.

We got our first Enterprise client. We got to go in and see people use the product first hand. Exciting and daunting at the same time. There’s always so much that can be done.

I broke my new Macbook Air screen. I frantically arranged replacement the week before leaving. I had to go back for a minor issue. I handed it to a guy in the lift. He disappeared with it and was gone for ages. I started to question whether I’d given it to an Apple Store employee or just a random guy. I freaked out. I embarrassed myself.

We booked flights to the US. We organised accommodation. I got my visa early, learning that you can’t take two laptops to a US Consulate visa interview and that Aussie rent-a-cops working in a US Consulate can be real dicks.

We flew to Melbourne to pitch. I got into my routine. Get nervous. Ruin the bathroom. Two practice runs while others pitch. Go!

I spoke too fast. The clicker I bought kept double clicking. I went OK though. People didn’t get our product. Not good but how many were target clients or investors?

We rinsed and repeated in Sydney. Twice. I learned that Aussie angels aren’t hopeless. They’re not idiots. They’re conservative. They play with a smaller pool of investments. They’re less likely to be able to personally vet a tech product. Their biggest problem, I felt, was a feeling that the more equity they took, the safer their investment. They don’t appreciate the power of founder motivation. Losing 50% in an angel round does not lay the groundwork for success. Angel valuations aren’t found with a formula.

We flew to the US. A mentor of Mike’s, Scott Petry, first assumed the role of lead investor. We needed more committed though or the round wouldn’t happen.

I pitched in front of Dave McClure at 500 Startups. I gave him my card afterwards. A dumb thing to do but he took it and followed me on Twitter. We met James Fitzgerald from Valar Ventures. He wanted to meet again.

We bounced from investor meeting to private pitch sessions and pushed to bring forward our Valar meeting. It was the right thing to do. We sat at the conference table in Thiel Capital. I tried to act cool as I looked out from the Presidio, across the roof of the Exploratorium to the Bay.

We were staying in Startup House. We refused to adjust for jet lag and mostly slept from 2am - 10am. The morning we needed to get up at 6am after a 4am wrap up was rough. We were forming very close bonds with our fellow Startmaters. We’d gone to war together.

I learned to play Texas Hold’em. I was frustratingly adequate at the game. We got drunk. A lot.

We flew to New York. It was fun. The demo day was quiet but we lined up a couple of customer meetings and one VC.

Mike and I stayed on past the allotted 3 weeks. Back to San Fran. Back to Startup House. We met some characters. “I have a website but you can’t get in”. “I was raising a $100M Venture Fund…. until I decided not to.” I renamed it Startup Hostel. Perhaps the “Bizzanes Home for Lost Entrepreneurs” would have been more fitting.

We hung out with Aussie entrepreneurs and were made honorary members of the Aussie Mafia. At least for one night.

The coffee in San Fran seemed to get better while we were there. The sun shone and the wind down 5th drove through me.

VC meetings were getting more serious. Due diligence checks started. We met with portfolio companies. We met multiple partners. We committed to moving to the US.

We weren’t getting much product work done. Fundraising was all consuming. We started having moments of doubt.

I told everyone who’d listen that I’d do a stand up gig. I painted myself into a corner. I’d never been more nervous. It happened though at the Brainwash Cafe’s open mic night. It was fun. It was twisted. I swore… a lot (nervous tic). “Pitch Practice”.

I prepared to pitch at the Citrix startup synergy event for a $100K investment. Mike provided words of encouragement, “This one is important. Don’t fuck it up”. The pitches were judged by a panel which included Jason Calcanis and Jonathan Siegel. We won the People’s Choice. Voting by the judging panel was closer. We went 1 up. We went 2 down. We were all tied at the end. A crowd show of hands didn’t break it. They awarded it to both companies.

We got coverage. Shit started to fall into place. Commitments started to come in. We got momentum. Mike closed someone we hadn’t met over the phone in 10 minutes on the 101. We lost one VC. The gap would be filled.

We reached the key inflection point of fundraising. The point where people stop being worried about losing their money and start getting worried about missing out on an opportunity.

We returned to Australia. Aussie investors were interested. Holy shit. We were going to close. A last minute US investment came in. I closed it using a twitter DM. I actually sent an email to their finance department saying, “I just confirmed the investment on twitter”. My grasp on reality was possibly slipping.

We oversubscribed. And then we oversubscribed some more. We closed it out. We never really celebrated. It’s a great thing but it’s not success.

Full focus was back on the product. Oh, and relocation. We would split the team. Support and backend dev out of Sydney to tap talent and be close to initial customers. Front end, marketing to the US. Leo here, me and Mike there. Easy to say, a bitch to do.

I took on a Co-CEO role with Mike. I wasn’t coveting it. He insisted. It didn’t sit right at first, co- anything with Mike is hard to fathom. I started to grow into it. It started to feel right.

The home front got crazy. The house went on the market. We started to sell all our worldly belongings. The stress pushed my wife to near breaking point. She pulled almost all of it off by herself. She is amazing.

The house was sold. The car was sold. Furniture, TV, washing machine, dryer, ladders, bikes. everything. A trailer load to the in-laws and we were done.

6 boxes booked for air freight and the rest of our stuff in 7 checked bags and 6 carry ons. Liberating. Scary.

An all too brief stop in Hawaii and here we are, San Fran bound. We look ahead to the next challenges. Finding a house to rent. Finding it in the right area to get our kids into the right school. Getting a car. Licences. Social Security numbers. Finding friends. Fitting in. Keeping my kids’ accents at least partly Australian. Oh, and continuing to build the business, of course.

Looking ahead now. I know what success in our game can look like. Do I see myself in that picture? It’s possible now but still hard to fathom.

Has it been fun? Yes. Has it been amazing? Yes. Has it been hard? Hell yes. Am I doing the right thing for my family or just myself? Am I anything more than a junkie seeking the ultimate fix? I don’t know. I may never know. I’m committed though. We’re all committed. At a certain point the question becomes redundant. “What else are we going to do?”, as Mike would say.

So I take a moment. I look back once more. I breath in deeply and fight to untwist the knot in my stomach. I raise a glass. Not yet to success. I’m still an Aussie. Optimism doesn’t sit comfortably. So I’ll raise it simply to the continuation of a life less ordinary.

Stay gold.