Joining a Startup as a Very Early Employee (VEE)

I joined Cucumbertown, a startup aiming to be the best food blogging platform in the world, 8 months after the platform’s launch. The team already comprised of 3 Co-Founders, 1 Developer and 1 Community Manager. I became the Product / Growth / Analytics / Business Strategy guy for the team. One and a half years later, Cucumbertown was acquired byCookpad, a public-listed food content behemoth in Japan. Now, at the time of writing this post, we are a 10-member strong team and expanding further.

Just 2 years ago, I only had startup folklores to refer to for imagining what is it like to be part of such a journey. Now, I have had a front seat and a role that of a navigator in a cross-country rally. Below are some thoughts for those looking to join a startup for a similar ride — specially if you are fresh out of college and are excited about becoming a part of this thing called a “startup”.

Image credits

Before joining

#1 Join before the startup achieves “Product/Market fit”

“Achieving Product/Market fit” is the first-among-equals in any list of gospel truths for startup success. Sufficient ink has been spent by stalwarts like Paul Graham, Marc Andreesen, Sean Ellis on this crucial objective.

The direction in which this beacon guides a VEE’s daily work is 100% dependent on the startup’s lifecycle stage — pre or post P/M fit.

  • Pre Product/Market fit

Delivery of Minimum Viable Product, lots of hypothesis testing, quick iterations, dirty hacks lacking code beauty, non-scalable approach to getting initial users, angst involved when doing a possible pivot, sometimes throwing out all hard work, and redoing all of this agin. A VEE must be quick, creative and free of hangups to flow fast with the speed of the startup.

  • Post Product/Market fit

Finding scalable growth channels, scaling infrastructure, setting up processes, narrowing work area focus to eliminate faults, handling tedious edge cases, ramping up customer support. Post P/M fit is all about making systems & processes scalable & fault tolerant. Execution focus is not so much on experiments but stabilising what works well.

Preferably, you should join as a VEE in pre P/M fit stage and then help transition the startup to a post P/M fit stage. A pre P/M fit startup in all likelihood will be unsure if it can even survive to raise Series A funding.

#2 Evaluate like a VC

A VEE is going to invest personal relationship sacrifices, health, sleepless nights, sweat, sometimes blood into the startup. Human capital is the only form of capital you own to invest. Protecting and seeking growth of this capital should be as important for YOU as the financial capital is for a VC.

Think like a VC before committing your precious human capital. Do your own due diligence of the business model and the founding team:

  • Evaluate size of the market

As Marc Andreesen has elaborated, a good market opportunity can result in a good outcome for the startup, even with a baseline competent (but not great) team and a fundamentally acceptable (but not great) product. This still does not ensure “success”, but does ensure no “failure”, provided the team and product are not totally screwed up.

  • Lookout for the Founders’ vision

Are the Founders aiming to fulfil a bigger mission / vision? Or is all the talk only revolving around how to ride the current hot trend? Gauge the Founders’ hunger for solving some fundamental problem for the users; the right execution team and market will take care of the rest. Lack of a such a vision increases odds of the Founders taking decisions to suit short term financial gains. That often results in hurting the long term prospects of a VEE.

#3 Trade learning over stocks (and office perks)

A startup can be the most rewarding place to get maximum learning for your time invested at work. The short-term payback of this valuable learning may not be much (in case the startup fails, which is 90% of time). But sets you up to reap huge dividends in your career in long-term. Aim to maximise your Rate of Learning. Don’t just get swayed by prospects of shiny office perks (in-house food, foosball table, terrace lounge). Or even by lure of stocks in a flavor-of-the-season company reporting stratospheric valuations (like, Secret). These don’t matter if scope of your role within the startup looks limited. Once a startup grows to a point where it starts establishing a organisation hierarchy, per person scope of work becomes more depth oriented than breadth oriented. You should aim to soak in as much breadth as possible, while simultaneously increasing depth in your core skills.

After joining

#4 Be ready to be surprised by the “real” problem you will need to solve

A VEE will often be handed what the Founders “think” is the problem to solve but will not be the “real” problem which needs solving. It takes a good discovery process (like, the 5 Whys) to find the “real” problem. Some examples. Personalisation — Not a machine learning algorithm problem but data cleanup problem. Dating — Not a user preferences matching problem but a bad offline experience problem. Many startups face the hard decision of pivoting to a different business model altogether when experiments around original thesis throw up critical problems which fell in blind spot of the Founders. Take a pivot in the right spirit, the Founders are trying hard to get things right. Just make sure that precious insights are drawn from inevitable failures and the new direction should not look like making same mistakes.

#5 Treat yourself as an Entrepreneur

Joining as a VEE will be closest you can get to the feeling of being an Entrepreneur without actually starting a business. Whether your role is defined as a Developer or a Community Manager, you should always be thinking about overall challenges in the startup’s growth. These maybe beyond your core responsibility areas. You should aim to appreciate the problems your Founders are facing. Forge a camaraderie with them; only possible when people together face adversities (like in a Army platoon). Such time invested as a VEE will be immensely rewarding for personal growth and help you make good calls later in your career.

#6 Solve problems by Running Lean

A startup is an exciting place where there are no set rules on how to attack a problem. This allows you to be creative and push your thinking. You could have a solution hypothesis, different from the Founders and rest of the team. None is right or wrong till implemented and results measured. Objective should always be to implement solutions in a manner to test your hypothesis as quickly and cheaply as possible. Aggressively measure the quantitative outcomes of a qualitative decision. Be on top of Build-Measure-Learn loop.

#7 Unearth assumptions, and then double-check

Your target may be — get 100,000 users to signup in next 6 months. Or, deliver a Newsfeed feature in 4 weeks. Work backwards from hard targets to arrive at core assumptions which need to be accurate for the plan to work. 100,000 users — what distribution channels, what top-of-the-funnel numbers for each channel, what conversion ratios, what cost structure? Newsfeed feature — what feed sorting heuristic, what frequency of updates, what backend optimisations? Raise a red flag if some core assumption looks wildly out of place. Will save you and the startup lot of wasted time and heartburn when plans inevitably fall apart due to bad estimation on these assumptions.

#8 Keep scaling up your skills as the company scales up

A successful startup, and you will hope for it, grows at a scorching pace. The tasks to be done to bring in first 100 users are very different to when you already have 100,000 users. The startup has to scale up processes and team to meet demands put in by traction. In an ideal world, skills of a VEE should scale up in tandem. However, in the real world, it is common for startups to hire industry veterans to manage stuff when the size grows bigger than what VEEs can handle. You may have been the early Growth Hacker in the startup, but be prepared to report to a Chief Marketing Officer, who was hired laterally when things grow big. Unless, you can scale up to meet the new demands of the organisation and take up bigger responsibilities.


This post first appeared on my blog.