Manufacturing Serendipity

Whenever I talk with someone interested in getting into startups, my main piece of advice is to “dive in headfirst and manufacture some serendipity.” What people fail to realize is that most startup jobs never get listed on a company’s careers page or posted on AngelList. Even if they do, it’s still likely the position ends up being filled through their employee or investor networks and not via a cold application. This is why serendipity is so important; you need to meet the right person at the right time. Fortunately, one of the most incredible aspects of the startup community is how open it is, which makes it possible to create your own happy accidents. Go to Meetups and events, tap your LinkedIn network, and tweet or email people you admire about grabbing coffee or beers. Your goal is to build relationships and create an opportunity for serendipity to strike. The way to do this is… just kidding there is no magic formula, sorry. What I can tell you about is the process I used when I was searching for my job after college, which will hopefully be helpful in getting you started.

Your first step should be to identify what type of startup interests you. Start with B2B or B2C. Next decide if you’re interested in SaaS, Marketplaces, eCommerce, etc. Finally think about what vertical: healthcare, sports, food, etc. The more specific you can get, the better. If you really have no idea, it might be good to focus on companies with good investors and experienced entrepreneurs on the team. This helps ensure that the relationships you’re working to build will have the best chance of being helpful. The next step is to create some targeted lists based on the startup profile you created. My list suggestions would be: companies you’re interested in and their employees, entrepreneurs or investors you admire, Meetups and local events. Remember, the name of the game is quality, so try to keep your lists short and ultra-relevant to the startup profile you’re interested in.

You’re going to want to join all the Meetups and RSVP to all the events you identified. When joining the Meetups, make sure to put some thought into your bio. People often review the attendee list before an event (I suggest you do too), so having a bio that will help facilitate conversations is key. You may even consider including your email address in case anyone wants to reach out beforehand to help ensure you two have a chance to meet. I would recommend going deep and becoming a regular at a few Meetups or regularly occurring events, rather than RSVPing to all of them and only attending each sporadically. Being a regular at the Hardware Meetup, rather than showing up there once and the SasS Meetup once will allow you to build real relationships over time, rather than just having one-off random 3 minute conversations.

When it comes to the companies, employees and thought leaders, I’m old school and use Excel to track this. If you want something snazzier, feel free to try a Google search, as I’m sure there is something out there for this purpose. Fill the excel doc with as much information as possible… Website/blog URLs, email addresses, social media accounts, etc. I’m not going to list out everything, but the goal is to take down any piece of information that you think is relevant and might be useful. My only firm suggestion is to make the 2nd to last column “interactions,” and the last column “notes.” Interactions is where you’ll keep track of just that, your interactions with that company or person – whether that be stopping by their office, grabbing coffee or interacting on Twitter. Notes is where you put any relevant information you learn about that company or person. Recently nominated for an award – write it down. Learned they’re bullish on wearables – add it to the list. Found out they’re a fan of the Patriots- you guessed it, add it in there. These two columns can provide great context when following up with someone or provide relevant talking points for any first or subsequent meetings.

Now that the prep work is out of the way, time to execute. I recommend starting with your LinkedIn connections. Hopefully you haven’t treated your profile like Facebook in the early days and gone on a connecting spree with everyone you’ve ever spoken a word to. Going with our quality > quantity theme, 100 real connections on LinkedIn are better than 1000 quasi-connections. Open your excel document and start typing in the names and companies into LinkedIn to see if you have any 2nd degree connections. If you do – great, now send that person an email asking for an intro. If you have some 2nd degree connections, but with people you don’t feel comfortable asking for an intro from then start by reconnecting with that person. If you come up empty on your LinkedIn search, it’s time to send some cold emails or @ tweets.

I want to point out that, I’m recommending sending an email, rather than sending a LinkedIn message. This is purposeful. I find that LinkedIn is most useful as a data source, and that you get more responses when leveraging email, followed by Twitter. LinkedIn should be your third option for when you can’t track down their email or Twitter. I think there is something to be said about taking the time to figure out someone’s email address, it shows that you went the extra mile and really care about reaching them. It shouldn’t be too hard to track down someone’s email address in today’s day and age, but if you need help learning the technique just google “finding anyone’s email address” and plenty of good articles should come up.

As for the Meetups, make a point of meeting at least one person at any event you attend – not including the host (although they’re a great connection to have). It’s really easy to go to an event and stay in your personal bubble, absorbing what is going on around you but not really getting involved. That’s why your goal should be to make at least one connection – no need to shoot for the moon, we want to make this an easily attainable goal. I want to reiterate that you shouldn’t spread yourself too thin and go to a ton of different Meetups. The point of the earlier exercises were too make sure you’re only attending the most relevant to your goals. As you become a regular, you’ll get to know the host and other regulars who can then help introduce you to anyone who only shows up semi-regularly.

Your goal for any intro, cold email or Meetup/event connection is for the two of you to get a coffee, beer, lunch or even some caramels (youtube scene). If that’s not possible for whatever reason, try to get an email correspondence going. You should do your homework before meeting; make sure you know about their background and what you want to talk and ask about in order to get the most of the time. If they work at one of the companies you’re interested in, ask about the team, culture, their role, how they got there etc. If it’s a less direct connection to your employment goals, ask about their background, how they got into startups, what trend are they most excited about etc. There is nothing more disrespectful than asking for someone’s time only to show up with nothing to ask them, just be careful not to make it seem like a KGB interrogation with too many or too rapid-fire of questions.

The final piece of advice I want to impart is to not be afraid of reaching out to anyone. Worst case scenario, they don’t get back to you… best case scenario, you get coffee with a total badass whom you admire. The more people you meet and the more strong relationships you form, the more chances you’ll have for serendipity to strike. So get out there and make it happen!