MSS Posts: Guide to Startup First Employees ๐Ÿ’๐Ÿปโ€โ™€๏ธ

6 min readOct 23, 2021


Mentality ๐Ÿง  โ€” Pros vs Cons (1/6)

Pros ๐Ÿ‘๐Ÿฝ: Rubbing shoulders with inspirational and visionary founders. If there is one base requisite it is this โ€” be inspired by the founding team!

Working around a group of people who genuinely enjoy their job makes needing to perform an easier task

Chances are youโ€™ll be given more responsibility. Fewer employees mean more versatility. Youโ€™re growing with the company. This means youโ€™ll be privy to more details and learning lessons. If you want to start a company of your own one day, this experience could be extremely helpful.

Usually, startups offer share options to make up for a lower salary.

Cons ๐Ÿ‘Ž๐Ÿฝ: 20% of new companies fail within a year. You need to accept the instability

At a startup, everyone is taking on a lot of work, which means there may not be a structure for training new employees. Some people thrive in that fast-paced learning environment, while others feel lost.

More challenges come with cultivating a successful company rather than maintaining a company. This means you could find yourself in the office long past 5 p.m.

Change is a constant, a project that was one minute a top priority is dropped for an urgent matter. Learn to not take things personally and read the signals.

Ultimately it comes down to โ€œDo you believe in the company?โ€

Everyone wants to be passionate about their work, but with startups, belief is especially important. Long hours, a lack of guidance, and unstable working conditions are a lot easier to handle when you love what you do.

Why startups make sense? (2/6)

An asymmetric opportunity is simply one in which the upside is much greater than the downside.

We live in a world where โ€˜a job for lifeโ€™ is a thing of the past. If you are a skilled worker, and you know your skills are valuable, you remain highly employable regardless of whether the startup you join is a success or otherwise

Look at a startup with a 5โ€“8 year timeframe. Is the potential outcome 10x any other opportunity that is available to you? Are you rubbing shoulders with giants that will catapult your career forward, and teach you how to build a company in a market you love and are excited about? ๐Ÿง

As per my earlier post, startups are hard work, and the instability plays with your mind. If you are intrinsically excited about the mission and the journey, it is hard to imagine how your life will be if you donโ€™t take the startup route

Do your due diligence, and ensure your partner and loved onesโ€™ are on board with your move to startup life.

A successful outcome with a startup can be career changing, both economically and in terms of opportunities ๐Ÿ˜ƒ. A failed startup means you need to get a new job ๐Ÿ™ƒ.

Hire slow, fire fast ๐Ÿ˜จ (3/6)

Culture is defined by people, not by messages on an office wall. The attitudes and habits you reward, tolerate and permit form the fabric of your startupโ€™s brand.

Hire for culture, train for role

I remember hiring a head of division who had a very credible CV and would likely fill the role with maturity and experience. As our startup grew, the role would become a leadership position.

The recruit worked with the right devotion and attitude,โ€ ๐Ÿ’Ÿ was in the right placeโ€

  • The quality of work was sub-optimal
  • Leadership had to constantly correct work done, and the recruit did not exhibit the confidence to be client facing
  • After many difficult conversations, no growth was observed over time

We let the person go. It took us more than 12 months to find the right replacement. Everyone in the team had to take on additional tasks to fill the gap.

Once the right person emerged, we put everything into bringing in this talent. ๐Ÿ˜ They took to the role seamlessly, and transformed the position to their own that reflected their personality and was an asset to our company and our clients recognised it immediately.

Itโ€™s not the hiring or the firing. Itโ€™s the training, support, and understanding your culture and what a fit looks like.

Contract Types ๐Ÿ“‘ : Freelance, contract, indefinite (4/6)

The world has changed, โ€œa job for lifeโ€ is close to obsolete, & the age of โ€œremote workโ€ #digitalnomad is upon us

Gig economy: A startup founder can get a quick fix โ€” e.g. logo designs, SEO work, etcโ€ฆ for relatively cheap

- gig economy workers see startups as just the next transaction

Creator economy ๐Ÿง™๐Ÿฝ: Sector expertise needed: E.g. marketeers, PR, videographers, campaign managers, event coordinators, designers

The relationship is beyond merely transactional, a culture and personality fit should exist

A good hire is someone who brings their creative dimension to the startup . Fees could be success based.

Contract worker: reflects the ebbs and flow of startup life ๐ŸŽข, Founders manage headcount as the market reacts.

- Niche experts can command exceedingly better contract values and earn equity

Personal Note: this is the position I accepted for my current work

Indefinite contract worker:

with reference to earlier posts on culture and mindset and future post on share incentives

Still today the default contract, at least for key hires ๐Ÿ”‘. Initially below market conditions, if the startup performs, thanks to your input and value add, these will transform into above market conditions, with share incentives as bonus.

Share incentives (5/6)

Note: For a technical, legal and local perspective, I highly recommend reading the primer by Seed Consultancy: Employee Stock Options

The central arc of this series is about the acquisition and retention of talent . A fundamental perspective to keep in mind is that great talent will attract many opportunities ๐ŸŽฃ. So thinking that your startup is the only possibility available to a talented hire is fundamentally the wrong approach

EVEN MORE SO if your startup is performing excellently well . Your top operators will get noticed, and offers will be thrown their way. I guarantee that!

Speaking from personal experience, I always did my best to be loyal to people that believed in me. But as the stakes grow, so should the terms of compensation and potential outcome .

Share incentives are a key tool ๐Ÿ›  to keeping talent long term. They align incentives, and provide the stickiness when things may not be looking so great โ€” especially when compared to offers being made

In the link is a brilliant little tool for employees to understand how share incentives play a role in understanding the value of a startup opportunity:

Share compensation tool:

Reverse mentoring ๐Ÿ‘จโ€๐Ÿ‘ฆ (6/6)

Your employees can be a source for competitive advantage.

I learned about this concept from a post on LinkedIn by Amanda Xuereb:

Generational gaps can be a base for creative conflict between executive leaders and the younger generation (or otherwise diverse) workers in that company.

During a session of this practice, the younger (or diversely inclined) employee would be given the opportunity to educate their superior on topics of tech, strategic and cultural relevance.

When selecting a hire, or vice versa a founder to work for, our uniqueness can be a source of value. Letโ€™s embrace diversity at the workplace! ๐Ÿง•๐Ÿผ๐Ÿง”๐Ÿฝ๐Ÿง“๐Ÿผ

This series of posts appeared on Malta Startup Space a Facebook group I manage that inspires startup culture in my native country of Malta ๐Ÿ‡ฒ๐Ÿ‡น

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AdiG Early stage company advisory and startup fund raising. Human connections that build relationships, add value and move the needle