How I landed my first startup job through a roadtrip

Part I: Introspection

When I shut down my first startup a few years ago, I had no idea what I wanted to do with my life. I was lost and felt like the thing I was meant to do — start a company — had failed and faded in an eerily quiet way. I had no fall back plan and the majority of my 20’s in front of me. I had to find a job.

I went into full soul-searching mode. It was honestly a pretty depressing time. I had a BS and MS in Finance, a little under a year of experience in tech investment banking, and a year and a half of being a tech founder. I could build a good financial model, design wireframes, and get people excited by making sounds with my mouth and expressions with my face.

What was I qualified for? Emceeing a Wall Street circus show? Selling confidence in a bottle?

After much deep thought, I decided I wanted to keep working with founders because, well, founders are some of the most interesting people on the planet. I had tried to start a company and failed. I wanted to see what a successful founder looked like. I had a huge blind spot in the success piece of things and that led me to two plausible plans, equally compelling.

The first was to be a VC. I had consulted with founders while starting my company and found that they kept coming back for advice. I enjoyed problem-solving with other people’s companies. I wasn’t emotionally tied to the company, I was emotionally tied to the people. One of my grey-haired mentors had worked with VCs for his entire career and told me I should seriously consider getting into venture.

The second option was to get an operational role within a startup. I’d work with smart people, build a rolodex, get a nice brand name on my resume, and leave the rest to Future Ben. This option was a lot scarier because I had no idea what I could possibly do within a startup. All I knew is that I didn’t want to work in finance. Other than that, zilch.

Part II: Extrospection

So I did the only thing you can do when you’re a failed founder crashing with your mom in FL between gigs: I made a huge list of people and started cold-emailing. Specifically, I emailed 400 senior partners at VC funds and dozens of founders who had just raised money. I also reached out to every founder and tech peer I had and asked for introductions.

My ask for VCs was simple: can you give me some advice about venture capital so I can figure out if it would be a better fit for me than working at a startup?

My ask for founders was also simple: do you have the budget to hire someone who will do all the weird things you don’t have time for or aren’t interested in doing?

basically, what I was asking VCs and founders in SF

I learned a few things in that initial outreach phase:

1. There are only about 100 active VC funds. The rest are either dead or in zombie mode.
2. Many VCs are happy to make time to chat. They know great founders often have failures before success and they want to meet you while you’re unknown.
3. Just about every single VC I spoke with (~20) miss their days working in companies. A lot of them look back at the beginning of their career with nostalgia and think about investing as the best job they can get with their current lifestyle and experience. Not a single one recommended I jump into VC vs getting a startup job.
4. Fellow founders were also really responsive but were more judging of my failure. A lot of them were really helpful but founders tend to be younger so the advice was a lot more granular and naive. The older VCs had more vague and wise advice.
5. Job hunting is a numbers game. Truth is, most successful people are busy. You just have to find enough people who have come up for air during your window of searching.

Part III: Grinding

Fast forward a few weeks. I secured 12 meetings in one week the following month. Friends and family helped in small but amazingly impactful ways. My mom let me borrow some money. Another friend let me borrow money as well. Troy let me crash on his couch for a week.

I flew to San Francisco with no idea what would happen. I had full days of meetings with VCs, founders, and operators. I caught up with anyone I knew here. I had a bunch of great chats and got a lot of solid advice.

I had 24 hours left in my trip but still, no offers.

Part IV: When Opportunity Calls

My last meeting of the week was at 4pm on a Friday afternoon. I almost cancelled it because I was running late but I rushed and made it from Embarcadero Center to SOMA in 10 minutes. My friend Amir introduced me to one of his startup advisors in SF who was running Product at Life360.

Both being Israeli, we found ourselves in an honest and energetic chat in Hebrew. I told him I just shut down my company and wanted to find work in SF in a startup. He used to be a VC and told me I should get a startup job, not invest. It would be more interesting and has more upside for someone like me, single and in my early 20's.

I asked him if he needed someone to help with business. He said he could see me as a BD guy (I was wearing a button down tucked into jeans and had a blazer on). But no openings were right.

“One second”, he said as someone walked over. It was the founder/CEO. They were talking about SXSW the following week in Austin, TX. They were planning to announce their partnership with BMW and needed to decide whether to bring their company car with them. Actually, they didn’t own the car yet, but they needed to decide whether to buy the company car to have with them in Austin to demo the software in the car.

A couple of the guys on the team were happy to drive the car back from Austin after the event but nobody was willing to drive the car from SF to Austin.

“You’re not busy for the next week, are you?”, he asked casually.

They told me if I helped them get the car to Austin and helped with some logistics during SXSW, they’d help me find a job through their network. All expenses paid.

My response

Part V: Learning Stick Shift

We bought the car together that night, a 2013 BMW M3, stick shift. I didn’t know how to drive stick yet, but I spent a few hours the next day with the founder, learning to drive stick on a performance car in the China Basin parking lot.

It started a lot like this

By the end of our lesson, I could drive without stalling on the highway. That was good enough.

The next day, I was on my way to Austin in an expensive sports car, unsure if I even knew how to get on the highway. 26 hours of driving and 3 days later, I was in Austin with the team. The Head of BD got sick and couldn’t make it. They transferred his conference badge to me. I had a legit badge with my name, picture, and Life360 on it. I worked with them the whole week.

decked out in company swag at the end of SXSW (I didn’t work there yet)

By the end of the week, steve vouched for me and said they’d be idiots to not hire me. The only opening was in customer support. So I interviewed for it and was offered a project manager role under the customer support umbrella.

Part VI: New Beginning

I took the job and started the following month. I was with them for 2 years and learned a ton. It helped me discover I love product management. I met my Breathe cofounder and countless other cool people over the years there.

There are a lot of details from my search that I spared but the bottom line is this: you never know where the offer will come from. You have to hustle, put yourself out there, and have faith that things will happen in some strange, mysterious way.

Have you had any weird job search stories? Would love to hear them!

the M3 that got me a job, taken at rest stop en route to Austin

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