Silhouettes of hikers climbing up a mountain cliff.
Corporate ladders are so 20th century. The idea of working for one company for the rest of your life doesn’t make sense in our on-demand culture, and the current career mentality of tech workers reflects this.
Reid Hoffman said it best. The entrepreneur and investor believes in what he calls tours of duty for tech workers. From his perspective, locking someone into a lifetime employment contract is unrealistic and it’s counterproductive to pretend otherwise.
David Booth, cofounder and CEO of On Deck, understands this. (In the interest of total disclosure, David is a former colleague of mine. And to underscore the theme, we only worked together for a matter of months.) His company hosts invitation-only events that introduce tech workers to potential cofounders and early employees. I interviewed him to learn more about On Deck and what it says about the future of company building.
The following transcript has been edited for brevity and clarity.
1. What problem are you solving?
David: The main one is a signal to noise filter and I think that’s particularly valuable, given the noise in the Bay Area right now. There are 10 meetups every day. There’s no end of conferences you can buy tickets to. There’s Startup Grind. There’s everything for everyone, but it’s very difficult on two fronts.
One problem is filtering through the surface layer of what people will tell you about themselves and really making a connection with someone. And the other is to dig through the sensitivity of people’s current employment status. You might be fully employed, but you’re interested in doing something new. You just haven’t told anyone that yet. Or if you have, you’ve told your manager, but you haven’t communicated that to the outside world.
2. Is this Soho House meets Triplebyte?
David: Soho House meets Triplebyte is a really interesting metaphor. The problem specifically is that the way we find cofounders is still rooted in the past.
It’s still very much like dating pre-internet. You end up marrying the people in the same small town that you grew up in because you simply don’t have a mechanism to find, and get to know, talent outside of that network.
The conventional wisdom is that people build companies with those who they have longstanding relationships with, which in most cases means that companies today are either suboptimal combinations of founding teams, or they’re simply not being built because, you know, the right people haven’t met each other.
3. Is this a new category like an accelerator or an incubator?
David: We have the ability to sit above that string in terms of a business model or investment metaphor. The thing that the best people need in the very early stages isn’t money. It’s talent and a community to bounce ideas off of to establish if they even want to be founders and what they want to build if they are.
And for that reason, I think there is no future in which we mandate that people must take our money or give us equity in order to participate in anything On Deck. I think that there are things that we can and will do to help people that don’t have the personal runway to be On Deck. There is some very interesting activity in the ISA (income share agreement) space for example...
4. The trust you need to build a startup in the first 18 months is very real. So much so, that some investors are dismissive of cofounders who have only recently met. How do you address that?
David: The best way to answer that is through the narrative of what On Deck has done as it has evolved. It started out as just these one-off dinner events. Erik Torenberg (cofounder of On Deck, Token Daily and Village Global) was leaving Product Hunt and he wanted to do something new. He emailed everyone he knew, myself included, in 2016, to say, “Hey, I’m on deck. Who else is interested in building something new? Let’s get dinner.”
And there were about 1,000 people who signed up for that first announcement, the Typeform. But for the first two-and-a-half or three years of On Deck’s life, it was always just these one-off dinners. It was organically run by the community, for the community. Erik in San Francisco, and then a few others stepped in to help run it. There was a guy in New York, and Tel Aviv in Israel. I launched London. I ran a few dinners and then I put it on pause for six months because I wasn’t in London. It’s the sort of thing you have to be present to run.
It was always left up to the individual to come to an event and, in the course of three hours, hopefully meet somebody that they wanted to build a relationship with afterwards. So it wasn’t saying you were going to meet someone and we’re going to create the environment in which you can fast track relationships. It’s that you’re going to meet them now and otherwise you wouldn’t have even known they were open to the idea of starting a company.
5. What kind of activities are involved?
David: It’s about the guests and what you can learn from each other. In the last fellowship, for example, there was a retreat. And every week, there’s a dinner and a co-working day. In each of those dinners or co-working days, there are at least four or five breakouts led by somebody in that group. Sometimes we have external guests come in. I mean, if you were in there, we would tap you and say, “Hey, do you want to lead a 45-minute session to talk about the future of media and building personal brands?” Not just you work at X, you can talk about X. More like what is this person an expert at? And giving them the opportunity to share actually allows them to connect with the group as well.
6. If it’s so common for employees to leave companies after only 18 months, why do you highlight secrecy on your website?
David: That’s a good question. We do very much front-load the privacy element. So every event has always opened with, “Pardon the introduction, but these are house rules. You can talk about what you learned, but not who you learned it from.” That kind of thing.
7. So less Soho House and more Fight Club?
David: Totally. We’ve been called Fight Club before. Yeah, first rule is you don’t talk about On Deck. I’m sure there are people who have opted out because they have feared for their privacy, but we have never had an issue. We’ve never had a reported incident where someone has lost their job or otherwise been adversely affected.
Lifestyles Of The Somewhat Vested
There are so many flexible work arrangements that we don’t have a sense of longterm dependency on employers anymore. Combine that with the widespread availability of venture capital and you end up with a company like On Deck.
Clearbanc, a startup that offers speedy income share agreements as an alternative to time-intensive fundraising cycles, believes in On Deck’s mission. In fact, they’re proud to hire future founders. Charlie Feng, a Clearbanc cofounder, told me that the company encourages their employees to start companies if they want to. And it pays off; one of their alumni just got into Techstars.
The application deadline for On Deck’s next cohort is September 22nd, 2019. And one minor correction, the original article said that a Clearbanc alumnus had gotten into 500 Startups when it was actually Techstars.
