Want a job in tech? Don’t get an MBA (& other observations)

An early-stage tech employee answers 7 🔥burning🔥 questions on acing startup interviews, compensation, failure & more

I was recently interviewed by my friend Sameer Syed about how to move from Wall Street to a startup. I’m often asked these questions by people looking to make a career change, so I wanted to share my answers in this post. For further reading on moving from Wall Street to a Startup, check out my other post here.


Q: Why did you pick an early-stage startup vs other types of companies?

A: When I left Wall Street, I had no idea what I wanted to do next. I had no grand plan, and owe any “success” I’ve had to luck as much as anything else. With that said, I tried to put myself in a position to get lucky. I wanted to quickly learn as much as I could about the job landscape.

To accelerate my learning, I talked to many people in many different industries (media, finance, technology). I treated networking as a full-time job, and arranged many coffee chats and phone calls with many kind people. I naturally gravitated towards those who worked at early stage technology companies.

These were the people who seemed

  1. Happiest
  2. Most fulfilled [different from happy]
  3. Most interesting
  4. To value things that I value, and
  5. To be building cool stuff 🚀🤖💻

I used those as guiding principles in my career exploration.

Perhaps more importantly, they were the ones who would actually answer my emails. Fortunately for me (and anyone trying to break into tech), there is an ethos in the tech world of “paying it forward.” This is one of the pillars that makes the NYC tech community great.

Q: What will I learn in my first startup job?

A: What you’ll learn will depend on the stage of company you join. The earlier stage the company, the more “hats” you’ll wear. The later the company, the more specific a role you’re filling. Early stage companies typically hire more generalists, later stage companies hire specialists.

Live look-in at an early-stage startup employee wearing many hats

One of the things I love about working at an early-stage company is the lack of bureaucracy. The scope of responsibilities you can take on is only limited by your imagination. If you bring curiosity, flexibility, and self-starting mentality, then you’ll be able to touch many different parts of your organization.

In my current role on the “business side” of a company with fewer than 10 employees, I’ve been fortunate to work on all of the following:

  • Fundraising: Talking to venture capitalists and pitching them on investing in our company.
  • Sales: Communicating the value that our software can provide to customers.
  • Customer Success / Account Management: Working closely with our customers to make sure they are successful when they use our software.
  • Product Management: Translating what our customers ask for into technical terms for our software engineers developers. This is something I had no prior experience in. I had never taken a computer science course or written 1 line of code. I’ve become (barely) conversant in the tech side of the business, taking courses in JavaScript and Ruby on Rails
  • Internal operations: The nitty-gritty of running a business. Payroll, insurance, accounting, investor relations, legal.

Q: How will my first role in tech affect my career opportunities?

A: The main currencies you will acquire in your first tech job are:

  1. Learning
  2. A good reputation

If you work relentlessly hard to get “rich” in those two categories, then your career prospects will increase exponentially.

Don’t focus too much on the value of your equity in the company.

A) Unless you are one of the first few employees AND your company is massively successful, you will not make life-changing money off of your ownership (equity or options) in the company.

B) Even if you do, it can take upwards of a decade to realize.

C) Employers have a lot of negotiating leverage since (seemingly) everyone wants a job in tech and you likely have limited directly relevant experience. Therefore, they may not budge on the amount of equity they grant you. Focus on getting the offer. Your most valuable compensation is learning and reputation.


Q: But what if my company fails?

A: Too many people overrate this concern when they’re on the job hunt. Yes, young companies generally have a risk of failure. However, there are a several factors mitigating this risk.

  1. In the modern workforce, particularly in tech, the expectation of staying with one firm for an entire career (let alone 3 years) is long gone.
  2. Failure (also known as experimentation) is not punished in the tech world. In fact, it is often taken to the other extreme, and celebrated. Unless you are the co-founder of the company, you are not likely to reputationally shoulder the lion’s share of responsibility for a company’s failure.
  3. You should aim to get an “MVE” (minimum viable experience) out of your first job. The definition of an MVE can vary, but I’d aim for 12–18 months at least.
  4. This means that when interviewing, you can (and should) ask about the company’s working capital / fundraising strategy. Be sure to phrase this in a positive light — that you are excited about the future prospects of the company and are curious about financial path to massive growth.
  5. Despite what you may hear, it’s likely that nobody (not you, not the VCs, not the founders), knows the true probability or magnitude of success. Be mindful of red flags 🚩🚩🚩, but don’t overrate your ability to forecast success.

Q: What is your view on going to Business School to transition to a role at a startup?

A: The answer here depends on a few different factors, but if you’re targeting an early-stage tech company, I would generally advise against an MBA. Here are 4 reasons against & 1.5 reasons in favor of an MBA.

TL;DR: Opportunity Cost, It’s Replicable, & Negative Signal.

Anytime I’m weighing pros vs. cons, I always think back to this episode of Boy Meets World where Cory puts jellybeans on either side of a scale to decide whether to stay Topanga.

Cons:

  1. Lack of early-stage tech opportunities: The later stage the company, the more robust their MBA recruiting program is. Google, Facebook, and Amazon are now some of the largest B-school recruiters in America. There are far fewer dedicated MBA opportunities at earlier stage companies.
  2. Opportunity Cost: There is a massive opportunity cost to MBA. This can be exacerbated if you have to take out loans. Do not underrate this and proceed with extreme caution before saddling yourself with financial obligations that cripple your optionality.
Seriously.

3. Negative Signal: Counterintuitively, an MBA can be a negative signal to startups. Some believe an MBA confers an air of know-it-all to its holders. Others believe that the entire MBA curriculum on creating corporate value is antithetical to the startup world. If you have an MBA, you’ll have to defeat these two objections.

4. Substitutability: Thanks to the internet, business schools are no longer the gatekeepers of the the raw knowledge that you need to succeed in “Business.” Such info is available on the web for free or very little cost. For tech, I list some resources here.

Pros:

  1. You’ll learn (some) useful stuff: I hold an MBA. Prior to business school, I had no financial background whatsoever. Seriously. I didn’t know the difference between “debt” & “equity”, and I had never taken an accounting class. Through the MBA curriculum, I learned these skills thoroughly. Without a doubt, they have been valuable tools in my arsenal for running an early-stage business. However, this is really only half a reason because: The question is not “was their value in acquiring these skills?” but rather, “were they worth the opportunity costs outlined above, and could I have learned them without the MBA”?
  2. Network: Depending on where you go to school, this can be very valuable. If you want to go into tech afterwards, make your list of target schools, and find alums from them doing tech-related things that interest you. They’ll have the best and most candid insight of anyone. I’ve seen many people create a powerful network — completely from scratch and without an MBA.

Q: How do I translate my existing skills when speaking to startups? How do I pitch myself for a new role role (biz dev, operations, etc.)?

A: One powerful lesson I’ve learned in the startup world:

Sales. Is. Everything.

Alec Baldwin’s immortal words from Glengarry Glen Ross

You sell your product to customers.

You sell the vision of your company to investors and potential hires.

You sell the mission to your current employees every day.

And when you’re interviewing for a new job, you’re selling yourself.

One of the most effective techniques in Sales is helping your “Customer” overcome their “Objections” to buying from you. Coming from Wall Street, or any corporate job, here are some of objections you’ll have to overcome, and potential responses.

Objection 1: “You’re way too expensive”

Sample Response: I’m under no illusions about the salary cut I’m taking to jump into the startup world. I’ve done research on AngelList, Glassdoor, and speaking to my network and am fully aware of the difference.

At this point in my career, I value finding a team, role, & company, I’m passionate about more than the difference in cash compensation. I plan on having a long career in startups, and view it to be pennywise but pound foolish to focus on the short term cash difference. In fact, I left my corporate job before I became trapped by the Golden Handcuffs. Now is the perfect time for me to make this move.

The Golden Handcuffs are real. The longer you stay the tougher it is to leave.

Objection 2: “You’ve never worked at an unstructured startup. How is anything you’ve done at [XYZ Big Company] relevant to working here?”

(Note, this is a hard question and role-specific. Below is a sampling of generic responses, but I’d suggest tailoring specific experiences you had to make it seem inevitable that your old job would lead you to this new one. It’s a good idea to have a custom resume for each job you apply for)

Sample Response 1: While the corporate world is more structured in some ways, it’s quite chaotic in others. I was often the only junior person staffed on several different projects at once. That means that I’m responsible for managing my own time and making sure time-sensitive “deliverables” get delivered. The nights spent at the office at 3AM when all managers had gone home were anything but structured.

It’s 3AM I must be lonely…

Sample Response 2: The culture at [XYZ Big Company] rewards self-starters. It was viewed as inconsiderate to ask someone else a question that could be easily Googled. When confronted with a question to which I don’t know the answer, I consult all resources at my disposal before leaning on a team member for the answer.

You do not want colleagues to think this every time you ask a question

Sample Response 3: As a junior team member, I’m responsible for coordinating calendars 📆 for meetings, taking notes, and staying relentlessly organized. I’ve learned painstaking attention to detail, can write clear, mistake-free emails, and understand how to drive projects forward.

Sample Response 4: One of the things I really enjoyed about [XYZ Big Company] was the collaborative nature of the work. Being a team player was critical to succeeding in a demanding, stressful job like mine. In fact, I was the person on my team [responsible for training the interns / who organized team social outings / who mentored other junior team members].

Objection 3 : “You’re too risk averse, and you don’t really want to work in tech”

Sample Response: I know that even the most promising startups have a high risk of failure. For me, the opportunity to learn in this fast paced environment and work on this exciting problem justifies the risk.

More importantly, “risk” is in the eye of the beholder. It may sound trite, but I view the biggest risk as not taking one. I’m only [x] years old, don’t yet [own a home, have a spouse / kid, insert other obligation], so now is the optimal time for me to take this risk.

To quote RENT…

Objection 4: “You’re not willing to lose your fancy title & do the unglamorous grunt work”

Sample Response: I’m not focused on title — a large factor in my leaving [XYZ BigCompany] is due to the bureaucracy. I’m excited to work in a flatter, more collaborative organization.

While I worked on some high-profile projects, I did plenty of the less glamorous work such as (name a bunch of unglamorous examples).

Objection 5: “You don’t truly care about the product or service we’re building, you’re a startup tourist.”

(This question is where you can really stand out. I frequently would put together very basic presentations in Google Slides and offer to do free work. Both major 🔑🔑s. Your goal should be to prove to your interviewer that you’ve walked through “The Idea Maze.”)

Sample Response: I’ve been learning a lot about this space and the specific problem you’re solving. I’ve actually put together this presentation that outlines (one or more of the following):

  • The tangible impact I could have in my first 60 days (including milestones)
  • Your company’s “go-to market” strategy
  • The competitive landscape of your industry
  • Your 5 biggest obstacles to growth and key questions I’d ask on the road to a solution.
  • 10 suggestions to make your company’s (website / app / social media presence) more effective
  • A blog post on why your company is excited about (news event X)

Additionally, I’m so passionate about this space that I’d love the opportunity to work on a project (for free) to show my dedication or commitment. Is there a discrete project I can help with to prove my worth that wouldn’t require a lot of training on your part?


Q: What are the salary & equity expectations I should have?

A: People on Wall Street are often tasked with valuing how much “things” are worth. Since humans are lazy, a quick shorthand is to look at what other, comparable things (“comps”) are worth.

You’d value a house by comparing it to others in the neighborhood, and you’d value the stock price of Toyota by comparing it to General Motors. Similarly, the easiest way ground your pay expectations in reality is to find out what comparable roles pay.

There are many ways to do this. AngelList, GlassDoor, & other websites that appear when you google Startup Salary data. Additionally, you can ask people in your network who might have insight into these figures.

The earlier stage the company, the higher the likelihood and magnitude of paycut you’ll take.

A rational (and more hopeful) way to look at the pay cut is that you’re making a bet on yourself. Once you come in and deliver a strong impact, you will be highly coveted by your current company, and highly attractive to others.

Remember you’re optimizing for learning & reputation.

**Disclaimer** — The above represents one person’s experience and advice (mine), so please evaluate it accordingly. Your mileage WILL vary! ⛽️⛽️

Please seek out many different points of view and advice when making an important, life-altering decision. And always question the conventional wisdom! Tiffany says it best:

Wise words from Tiffany Zhong

Thank you for checking out my post! Please let me know what you think and if I can be helpful in your search! Twitter: @CantHardyWait

🙌🙏 Finally, a HUGE thank you to Bez, Tommy, Nikhil, Ace, & Khe for reading various drafts of this and providing massively helpful feedback!