Should I Start my Career at a Startup or a More Established Business?

Should I Start my Career at a Startup or a More Established Business?

Question: Is it a good idea for me to start my junior career at a startup, not a big corporation yet?

John: Yes, so let me just give you the benefits. The benefits are this: you’re going to have an outsized title that you don’t deserve, you’re going to have a set of work responsibility that, likewise, you don’t deserve and if the startup is successful, if it’s got five people now when you join and it grows to twelve, you’re probably going to grow with that and you probably have managerial responsibilities once it grows to 30 or 40 folks so…and you won’t deserve those either but with no one else around you, you will. So, if you want to go be an intern at Procter and Gamble and look at how many units of cereal was sold in one particular Wal-Mart in South Florida, you go to that. If you want to be an early employee at a startup, your job responsibility may literally be Director of Marketing, over something similar to that, so no I think for the most part it’s a really good thing, there are some caveats though.

Blake: so, what if I qualify as an unpaid job at a startup?

John: so then it’s an interesting thing, so it’s completely unpaid then it’s just like an internship and that’s not super sustainable, yeah do it for a couple three months if it’s an entree to get a real job and you can build your portfolio or your resume, if they’re offering you plain equity for that, look at it is zero dollars, because most startup’s fail unless you’ve got a multiple time, successful, startup founder, most of them are going to fail, even us, I mean here we are here at Engine, I mean, what am I? 4 out of 7 in my career? that means we’ve got like a 50% chance, maybe a little better if we’re, if we’re lucky. So yeah that qualifies it a little bit, just you know, what are your responsibilities? Are they more than you would ever dream to have at a real job and if so, go do it, especially if the pay is you know, enough to buy ramen noodles and pay your rent, that’s…

John Max: one thing like, it’s also a measure of how do you…how do you work best. If you need a ton of structure in a job? If you need someone who clearly defines your role and it doesn’t change? 

John: Why are you here where? you could, you could…you had this route, you’re running your own agency, you could have easily gone to do the Proctor route, higher up than the one store with what… Why are you here?

John Max: so for me, very personal decision, so to give you all context, ran an agency, a paid media acquisition, mainly for e-commerce, and started to get to know these guys and through that, through that series of engagements conversations, I really felt that I could add a lot to the team here, was lucky enough to be offered a position and quite frankly for me, it was it’s a step back to take two steps forward. From a pay perspective, it’s a step back, but from a working with people who are much smarter than me, much more educated, mentorship and being a part of a team that is going to move incredibly fast, I was bought into the thesis of the company and I was bought into the team behind the company and so for me it’s a blessing to be able to join…it’s a blessing to be able to join a company of, what I consider, some of the best practitioners in the State, if not the South, and so…

John: when we scale to 30 employees, you have the same kind of vision, you’re going to be probably two levels…I mean you’re running marketing for us, you will be two levels higher than that with a team of teams, if we scale to that point, so…

John Max: and if it…and this is a thing when you join a startup, you have to be OK with it failing, and understand that it’s nothing but positives that are going to come with that, you don’t want to…

John: You can’t be OK with that!

John Max: you’ve got it…you’ve got to have a conversation though, and for me, if this company literally did nothing, I would still be better by being here and learning and just absorbing being around people like you all.

John: You can’t be OK with it, your wife has to be OK.

John Max: It’s true, I want to cap this off…

John: We could be on this for hours…

John Max:  I want to cap this off though, talking about titles, don’t give the C.E.O. of your company the job to name your title.

Blake: I thought you did a good job.

John: well it was really cool, and you know, we signed off on it as the leadership team, underling that was officially on his stock option grid currently, and it was good, and it wasn’t even capitalized if I remember correctly, it was all lowercase.

Written by
John James, M.D. is the CEO of Engine, a modern cloud-hosted ecommerce platform. I paid for medical school with an ecommerce business I founded in my dorm room over twenty years ago, and eventually raised over $100 million in venture capital running Acumen Brands. Email me -- john at enginecommerce dot com.