Startup Career Advice for Recent Grads & Corporate Staffers

Curious about getting more involved in startups? Interested to know why I love working for them? Curious reader, this post is for you. Read on…

One thing that I love about writing a blog getting and responding to reader emails. The questions asked are often stuff I talk about on the blog so sometimes I decide to essentially repost the thing on my blog [1]. I wrote a post earlier this month on having too many ideas and not executing that was prompted by a reader email. Well, it’s happened again. I got in touch with a dude named Nick who’s got a corporate job at Target but want’s to get into startups. Here’s what he said:

Hi Jason,

I came across your site while looking for advice on working for startups. Your entry on how to get hired by one was really helpful and, after going through many of your entries, I really admire what it is you do. I personally graduated from the University of Southern California (USC 2010) after an abroad stint in Thailand and realized my love for entrepreneurship/leadership later in college, which pivoted me away from pursuing a finance career.

As a result, I’m currently part of an executive management program for Target Corporation, where I manage an Assets Protection team that resides over a $60M sales/yr store.

In the next year or two, like you, I plan to be part of a close-knit entrepreneurial team to be part of companies that make positive social impact.

I’m sure you’re extremely busy, but I really admire your success and was wondering if you might be able to chat on the phone for just 20 minutes. I’m fascinated by your career and would love to learn more about how you got to where you are.

Thanks for your time and I look forward to hearing from you soon!


Nick is clearly a driven and accomplished guy who has a good sense of what he wants to be doing next. His email gave me a bit of info on him (which is important), but his somewhat vague request to learn more about my background made it harder for me to write back with something of value. And since I had never met this guy, I didn’t necessarily want to start blocking off precious evening hours to chat with a stranger right off the bat.

So I pushed back on him and asked him if he had more specific questions I could help answer. He obliged with the list of great questions seen below, and even followed up after I didn’t get back to him after a few days. Good man. So let’s cut to the chase:

Startup Career Q&A with Jason and Nick

How did you come to realize that you wanted to work at a startup and what qualities make you successful?

It’s been a slow journey / process to learning about my interest in entrepreneurship. I think the first time was when I created a book called Stanford Spirit essentially from scratch and sold 50 copies to my college bookstore. The fact that I, over the course of a year, took something that was purely an idea in my head and brought it into the world, was a really awesome feeling.

I then got involved in more student groups and I think starting or leading a student group is often much like running a startup – you’ve got to recruit and organize the work of a bunch of talented individuals to do awesome stuff with limited time and resources. I cofounded a nonprofit my junior year focused on student entrepreneurship and microfinance which really turned me away from the idea of research or medicine (I was a biology major) to the idea of creating not just products but organizations from nothing into something awesome.

I’ve always been interested in exploring new technologies (especially stuff online) and eventually realized you can work at the companies that build this cool new stuff. So finally I put two and two together and here I am! Doing all these things I mentioned earlier + reading lots of startup material has helped me develop skills and attitudes that I think will make me successful (though the jury is really still out on if that actually ends up being the case). This include in no particular order:

  • a bias for action
  • really enjoying working closely with people
  • a strong urge to create and have creative ownership of my work
  • learning quickly
  • being persistent in face of obstacles / challenges.

I’m looking to switch career paths – I’m currently part of a management program for Target Corporation and have a great set of leadership/time management/performance management skills. How are these skills applicable for an entry-level startup job and how can I highlight what I’ve learned to them?

I’ve heard great things about the Target internship (definitely looked appealing when I was a senior). While I’ve never personally worked a corporate job, it seems like you can potentially gain some valuable skills there: the disciplined setting and measuring of team/personal goals, being held accountable for delivering results, taking a long term, holistic perspective on decision making, good communication skills (email, phone, one on one, small group, big group), professional training and development opportunities, being diligent and consistent and conscientious about your work.

There are of course potential downsides of working a corporate as well: the work (and therefore people) are often slow moving / slow to change, you are less resourceful because you have some much money / time / manpower at your disposal, you learn more about pleasing your boss more than getting results, your skill set is too specialized, you hare not a hustler, etc. Your best bet is to do whatever you can do to emphasize the positives and show how the negatives don’t apply to you.

I’ve written much more on this topic in post How to Land a Killer Startup Job Out of College

When applying to startups, what pitfalls would you avoid?

Avoid spamming lots of startups – focus and really go deep with a few at a time. Recognize there are a limited amount of business positions. Be willing to take a “lower level” position like customer support as a starting point. Don’t be too formal – figure out creative ways to 1) get their attention and 2) demonstrate you know your stuff and can deliver results.

What is it that you love most about what you do now?

I love directly interfacing with customers and representing the company. I like being thrown into new situations, going into business development meetings with my CEO at big companies, sitting in board meetings, closing deals with big customers, bringing in more revenue, trying new things like implementing analytics software or managing a team of virtual assistants, planning out our long term strategy & pricing models, learning about how our databases are configured, etc. The doing everything and moving fast and learning lots appeals greatly to the action oriented, ADD personality I have.

I wrote more about my startup experiences in my posts Things I’ve Learned Three Weeks at a Startup and 21 Lessons Learned 21 Weeks at a Startup.

I can only imagine that working at a smaller startup like isosocket requires a lot of personal time and long nights (not that it’s a bad thing), so how do you manage your personal work/life balance?

Time management is hard. So far it’s been pretty even keel at isocket (though this month and the months ahead are definitely more intense). It’s more the mental energy of thinking a lot about the business outside of work and the being potentially on call / on duty at a random time or on a weekend.

I make time to work out (sometimes at work as we’re doing the 100 pushup challenge) and see friends 2-3 times a week to stay grounded. I also blog because it helps me internalize what I’ve learned, meet new people (like you!) and develop my personal brand outside of my job. Sleeping is something I don’t do enough of, but somehow I’m making do with about 6 hours a night. Hope I can keep that up.


[1] My buddy Sebastian Marshall really likes doing these kinds of posts. I’ll be honest, sometimes I see those posts and I think Man, I want to know what Sebastian thinks, not read his specific responses to some random guy’s questions. So part of me hesitates, because I’ll see that it’s a direct response to a reader’s letter and think “This post isn’t for me, it’s going to be specifically for that guy. But then I’ll actually read the post and at least half the time I find it really valuable.

Also, I realized that because the writing is more specific, if you DO share the same interests / questions as Nick, this post will be twice as interesting as a normal post. Also, I hope this post encourages more people who have good questions to email me because they see that I’m really open to that kind of thing.

Oh – Nick and I have now scheduled to talk on Skype and I’m looking forward it. :-)

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Jason Shen

Jason is a tech entrepreneur and talent expert. He is CEO of a performance hiring platform called Headlight, a Fast Company contributor, and an advocate for Asian American men. Follow him on Twitter at @jasonshen and subscribe to his private newsletter.

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  1. Good post.

    Yeah, I do like answering questions. Actually, I think like 90% of my most popular posts are responses to questions, responses to someone, or a reaction to someone else’s blog post.

    Eliezer Yudkowsky and Derek Sivers both write about this – a lot of times we think everyone knows the same stuff as us, we think our insights are really basic and we gotta come up with something advanced.

    But often times, a good answer to what seems like a really simple question will be really helpful to people. I think a lot of times we don’t realize how some basic parts of our lives are unexamined, so when I see someone whose insights I like writing about what bank account to get, or which retirement account, or their diet, or what they do first thing in the morning, or how they manage their email – these might seem basic, but if you get a small optimization in a basic common part of your life, that can be worth *a lot* – so yeah, I like questions, even really basic questions. I also like sometimes asking even really basic questions to people I respect – it’s amazing what kind of insights you can get that you never considered before.

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