Spotlight on Adam Hesch

Meet Adam Hesch: A Navy Veteran whose journey into Silicon Valley started with a spreadsheet of 200 startups and a one-way ticket to San Francisco, he shares with us some crunchy, tactical stories on the similarities between the military and startups; advice on how to crush the job search; and what life is like as a veteran.


What similarities have you seen between the military and entrepreneurship/startups?

Oh man, so many!

I think the historical examples are the most interesting ones -- probably easiest to highlight the similarities through common principles:

  • 1. Joining the Team: If you want to join an industry/startup/organization but keep getting told no, be willing to take entry level jobs, work relentlessly, and prove your value.  You’ll either be given more responsibility or find a new opportunity to start your own impactful venture.

  • A. ZeroCater CEO Arram Sabeti spoke at HustleCon a few years ago about his obsession with finding a way to get involved in startups in SF. He applied to job after job after job and kept getting told no, until his enthusiasm during an interview caught the attention of Justin Kan, where they actually made an entry-level position for him at Turns out during his time there, he created a curated spreadsheet of places to get food that other startups wanted to get their hands on. This demand eventually turned into Arram becoming CEO of his own company,  ZeroCater, a $100 million catering company!

  • B. At the beginning of his career, Draper Kauffman (who went on to eventually found the Navy SEALs) was initially rejected from joining the Navy for having poor eyesight. Having heard about the danger of Nazi Germany as a young man and determined to find a way to make a difference anyhow, he showed up in France and signed up as a volunteer ambulance driver on the front lines of the war. This enthusiasm caught the attention of the British Navy where he later applied and was accepted to get into Bomb Disposal. He then later used this knowledge to get the US Navy to grant him a waiver and go on to found the highly successful Underwater Demolition Teams in the U.S. (the precursor to today’s Navy SEAL’s)!

  • 2. Do Things That Don’t Scale: In his essay “Do Things That Don’t Scale”, Paul Graham shares a number of lessons that, in my mind, parallel the many strategies employed by a legend in Naval History, Admiral William Sims.

  • A. Recruit. Paul shares the story of the early days of Stripe, when its founders started manually and aggressively acquiring users one at a time, instead of worrying about scaling from the start. When he was trying to sell the disruptive idea of Continuous Aim Fire in the early 20th century, LT Sims ran into roadblock after roadblock when trying to scale his idea by sending essays straight to the Navy’s Bureau of Ordnance. It was only when he  traveled throughout the fleet, speaking to the Officers of each ship, one ship at a time, that his idea eventually got traction and scaled to help keep the US the dominant naval power in the 20th century.

  • B. Fire (focus on a narrow market first). Paul shares the analogy of starting a fire by focusing on getting a small amount of wood really hot before growing a fire as the same way to approach scaling by first entering a narrow market and then growing from there. The example he uses is Facebook first limiting itself to Harvard, and then Ivy League schools, and so on. When Admiral (then Lieutenant) Sims started his career as an innovator, he focused on the area of Gunnery. Once he was able to disrupt and scale the way the entire Navy approached Gunnery, he then moved on to help disrupt Naval Aviation, Submarine Warfare, and Convoy Patrols across the Atlantic during World War II.

Of course there are differences between entrepreneurship/startups and the military, but I think many people are unaware of how similar they can be.


You have a gift for helping others find their dream job. What are some pieces of wisdom our readers can apply to their own job search process?


Oh gosh. So many. I wish there was a giant sticker slapped at the top of every job board saying “Resume Black Hole of Death Below: Enter at Your Own Risk”!

  1. Network strategically. This sounds obvious, but a lot of people build a network without knowing how to leverage it. I’m going to go ahead and assume people know how to build a strong network because of all of the good advice I see in the NGS group :) Now, here’s how to leverage it:

    A. Have a specific ask, make it easy to say yes, and cover all your bases:
  • i. If you’re applying for a Product Manager role at a large tech company, but met a Security Researcher from that company a few weeks earlier, you might not be able to ask them too many PM questions, but you can (and should) still ask them about company culture, the interview process etc.
  • ii. When requesting a phone call or meetup for coffee, always suggest a few times, limit the duration to 15-30 minutes, and come up with thoughtful questions ahead of time based on research. This will show respect for their time, impress the heck out of them, and get you nuggets of knowledge they wouldn’t have shared if you had asked simpler questions.
  • iii. End each conversation with: “Do you have any recommendations for anyone else you think I should be speaking to, and if so, would you be willing to provide an introduction?”
  • iv. FOLLOW UP. In the “virtuous cycle” of meaningful networking, your success (and failures with lessons learned!) are ALWAYS other people’s success. So, so many people overlook this. Once people connect with you, they are invested -- they want to be a part of your success. Write thoughtful thank you notes, update them on your progress, and stay connected with them. There are zero humans that don’t value meaningful connection; there are millions of humans that feel burned when someone they’ve helped lets that connection drop off. Schedule it on your Google Calendar, put post it notes on your refrigerator, whatever it takes. Follow up.


  • 2. BE SPECIFIC, WITH EXAMPLES, FOR EVERYTHING. If you want to get people to hear your story like a bee flying to honey, say “Can I offer you a specific story of how I’m stuck, and get your advice?” People will go crazy for crunchy, tactical, specific stories -- especially ones they feel they can help with. Maybe you don’t know a lick of SQL, but you’re a genius when it comes to Excel Pivot Tables and Charts -- that’s amazing! Then you can nerd out with a Data Scientist on recommended next steps to build your skillset.


  • 3. Never ever (ever) apply to a job at a company without having first spoken to AT LEAST 3 people who either 1) work (or have worked) at that company 2) work (or have worked) in that industry 3) work (or have worked) in that role. And to be Captain Obvious: those thoughtful conversations should be based on your own preliminary research.  This sounds challenging, but will skyrocket your chances of getting an interview and landing the job. Otherwise enjoy sending hundreds of resumes into the Resume Black Hole of Death.


What is life as a veteran like, and what have you been up to since you left the military?

You know, on the whole, I feel extraordinarily lucky to have been able to serve in the military of a country that is so Pro-Veteran. It’s hard to drive on a street without seeing a “Support the Troops” ribbon on the back of a car; people who disagree with our foreign policy by and large still respect those who’ve chosen to serve (who are legally obliged to carry out that foreign policy); and many tech companies (like Facebook, where I landed after getting out) have programs focused on utilizing the skillsets of veterans, which is awesome.

On the other hand, I do think leaving the service can still be a challenge. You can feel a sense of guilt when you get out for feeling you like you’re leaving behind those still serving in harm’s way; the language barriers between the world of the military and the corporate world couldn’t be more different; and I do think the average US Citizen is much further removed from the world of conflict overseas than they were say after World War II, and this can create a sense of disconnect in soeciety at times I think.

To follow my own advice of being specific, if my dreams could come true, this is how I’d improve the connection between veterans and civilians:

  1. Sharing Stories of Battles. To be a human is to experience suffering and struggle -- it’s not just veterans who fight battles. A buddy of mine threw an event at Stanford called Whiskey and War Stories where veteran students shared stories of their service to their civilian peers. I loved that idea -- but I think we all have “War Stories” we’ve been through, whether it’s family challenges, discrimination in the workplace, seeing a loved one battle cancer etc. I think more community story-telling about how we each fight our own battles is deeply needed, with laughter, crying, all of that. Oh, and Whiskey.

  2. A Satirical Civilian-to-Military Dictionary for Recruiters. I think it would be possible to write a respectful but funny dictionary of sorts that makes fun of the stereotypes in both the Military and Silicon Valley by comparing them to each other. A few that come to mind: the Product Manager who is awful at coding, and the Army Lieutenant who is awful at navigation (you can’t spell lost with “L” and “T” goes the joke - the abbreviation for lieutenant); CEO’s and Commanding Officers whose life philosophy is leadership-by-email; Managers and Officers - you can start getting work done when they go home for the day, etc. Laughter is always the best starting point for meaningful conversations.

As far as what I’ve been up to since I left - lots of stuff! In 2015 dove into the world of Social Media & Partnerships when my friend invited me to work for him at UPLIFT Aeronautics, a since-shutdown drone company focused on humanitarian aid. I learned a ton there and helped get us featured in FastCompany! I then wanted to get involved in startups so I followed Parker Thompson’s advice and hand-curated a (now outdated) list of 200 startups, bought a one-way ticket to San Francisco, interviewed at 10 of them, and finally realized Facebook was actually the best landing spot for me, where I’ve had a blast ever since.

Lastly, I’m also starting up a Career Coaching business based off the many lessons learned the hard way (and subsequent multiple offers I received!) while living In Silicon Valley. I started doing Pro Bono coaching for my friends and realized I was on to something when they started consistently landing jobs at places like Tesla, Twitter, Palantir, ertc

If you know anyone struggling to land a gig and who’s serious about wanting get a job in tech, feel free to send ‘em my way at :) 

Haley Smith