How to decide where to spend your time

35+ million jobs and counting have been erased due to Covid-19. More people than ever are thinking about what’s next for them. I am one of them and so is the entire team I managed. Everything happened with incredible speed. We spent 5 years building a marketplace and poof it was gone in 3-4 weeks. After you get over how stunning and bizarre this time is you are left with a question of what to do next. The following is a summary of the guidance I’ve shared with my former teammates.

A quick level set:

  • I err on the side of high risk high reward. I’ve never not started/joined a company at its earliest stages where there’s increased uncertainty. I’ve seen stability but its never been from the start - only after we achieved it together. Thus these points map to earlier stages of careers but depending on ones risk tolerance could apply more broadly.

  • Also, I’m fully aware the number of unemployed far exceeds the number of unfilled jobs. If you don’t have the time it takes to find a great fit then do what you have to do.

So, how to choose where to invest your time? Setting aside personal exploration (which this is a great time for!), if you know what you are good at and the role you want to play, here are some things to consider when assessing an opportunity:

Asymmetric return on your time

If you break it all the way down, being employed requires you to invest your time and effort in exchange for monetary compensation. Hopefully you can learn or improve a skill while doing the job. Look for an opportunity to invest your time with an asymmetric return on learning & compensation.

Joining an early stage venture means that the company still has a lot to figure out. The established processes of a mature organization are not yet in place. That means someone has to build them! That someone could be you, even if you’ve never done that thing you need to do before. This can also apply to larger organizations if there are new divisions created within them etc. However, when compared to joining an established company with refined roles, the necessity of employees at start-ups to “wear many hats” more often than not results in an asymmetric learning return on their time.

The downside is that base compensation is often less than can be obtained at a large company. However, that should be offset by equity. Equity is alignment. It allows an employee to participate in the upside value creation as a result of their efforts. It also ensures you aren’t just renting out your time for a paycheck. To cite the infamous Naval, “You don’t get wealthy renting out your time.

Small pond with a river to a blue ocean

Now that we have a basis to think about the return on your time let’s talk about how to choose where. To be fair, company success can be random and unpredictable, but there are some things you can look for to make an educated bet on being an early member of a highly successful company.

A good disruptive product creates value by shifting customer behavior. The most valuable products & services have a large total addressable market. Disrupting a large TAM all at once is really hard. There are numerous examples of highly successful companies starting with a niche to establish traction and then expanding outward. Facebook started with schools, Uber with black cars, you get it. Look for a company starting in a small pond that has a river to a blue ocean.

The goal of Ritual is to digitize local commerce. Tall order! The task becomes more achievable when you start small. We identified the segments of supply and demand that stood to benefit most from shifting to digital payments and started there. From a merchant standpoint, Ritual started with quick service restaurants and coffee shops because the order frequency is high and the average order value is low. This allows for consistent use & removes a cost barrier to entry. From a demand standpoint, we looked to best exploit the convenience of a digital order. The people who are most pressed for time are corporate workers in a highly dense environment. Once this approach proved successful we expanded to residential neighborhoods and hopefully soon there will be other verticals.

Work food —> everyone food —> all commerce

This wasn’t and still isn’t completely apparent to an outsider. Look for a product or service that has a focused starting point yet could be applied to many other segments. It may not initially be visible on the surface level.

A good product and forward thinking leadership

If these aren’t high quality the above doesn’t matter because the company won’t be successful. You won’t skate to where the puck is going if you don’t have forward thinking leadership. Your individual job will prove much more difficult if there are issues with the product.

Is the product good?

  • Look at how much traction it has and how long has it taken to get it.

  • The self test is so simple yet often over looked. If its a consumer product do you use it? Would you use it? Why yes or why no? Beware of confirmation bias and be objective with your assessment. If B2B find someone in your network who has more experience with the vertical and ask them.

  • Ask their current customers what they think. This is much easier than you might assume. It also shows effort and gives you ammo for an interview. If its software look at G2C.

Forward thinking leadership:

  • The most successful companies carve out new categories for themselves. To do so, leadership has to have a vision to plot the course of the future. Look for multi-step ahead thinking resulting in believable evangelizing communication from the CEO. Put differently, a logical vision of the future and ability to set the course to get there.

  • If members of the team are only talking about right now during the interview process that is a poor sign. This is especially important given the current conditions. What’s their plan?

  • Demonstrated success. Have they done it before? A team with previous experience has banked many valuable lessons learned which will help navigate the inevitable bumps in the road.

Once you think you’ve spotted an interesting opportunity there is bound to be A LOT of competition so be bold in your pursuit. Craft your communication not about what you want (the job) but about what they are looking to solve. Go to the top and tell them why you are suited to help them. If you are having trouble getting in touch create a targeted LinkedIn ad to stand out. Identify what they care about and speak directly to that. Remember, they don’t care about what you want, they are looking to solve their own problems.

**Depending on your career the question of how to spend your time can be answered in many ways. What are some other ways to think about this?

Stay safe & good luck out there.

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