The other day, I was chatting with a guy who works at a restaurant down the street in the South End of Boston. He was telling me it was his last couple of months at the restaurant as he had just graduated from college. He said he wanted to get his money's worth for all the money he spent on college, so he was going to get a higher-paying job in residential property management. He seemed like a sharp guy, so I had this impulse to tell him to get into tech. But I hesitated and decided not to.

I sometimes forget that tech requires a certain personality. A high tolerance for risk. And I didn't really know the guy, so it didn't feel right to try to direct him one way or the other.

With the relatively high salaries in tech, flashy products, and nice perks, it's easy to forget how volatile and risky the space actually is. It's definitely not for everybody. And if you're not the type of person who can handle booms and busts, stay away. There are plenty of other less lucrative but far more stable jobs to get into.

It's worth remembering why this is. Tech companies, by definition, are investing in high growth that comes from new ideas. Investing in new ideas is risky. They often don't work. The greater the risk, the greater the potential reward. In boom markets, working in tech is great. In busts, it's not. I’ve been through 4 of these downturns in my career — the 2000 dot-com bust, the 2008 Great Financial Crisis, Covid in 2020, and the end of the low interest rate period in 2022. None of these were fun, and all of them came with a great deal of professional stress and anxiety.

Because of things outside of your control, such as interest rate changes, investor sentiment changes, geopolitical events, new technologies, government policies, etc., tech markets are inherently cyclical. And the risk takers that are putting capital into new ideas always feel downturns first, because that's the capital that investors will pull out and put into safer, less risky investments.

Before embarking on a new career in tech, make sure you understand this reality and are up for the dramatic ebbs and flows in your day-to-day life that are a natural, unavoidable part of working in this field.

Managing different investor priorities, objectives, and incentives is one of the most difficult things to do when leading a company. I wrote about the importance of understanding your investor's context and incentives a while back. Even at the venture stage, your angel investors and VCs may have very different ideas on how they define a good outcome. Depending on their own situation, some may be taking a very long-term view of the investment; others may want a shorter-term win. This intensifies significantly as you transition into the growth stage and, ultimately, an IPO, at which point you can literally have millions of investors with competing needs and priorities.

To help manage this, someone once told me that in a board meeting, I should try very hard to step out of my own incentives and not behave on behalf of Brian Manning but instead behave on behalf of the company. The company has no voice. Everyone in the room has their own incentives and that's typically what they represent. It's important for someone to step up and speak for the company.

This sounds like great advice, but it's almost impossible to do because how does one define the incentives of the company when the incentives are really a bundle of competing self-interests? This makes driving investor alignment extremely difficult.

As a leader, your job is to maximize shareholder value, but on what timeline? Should you optimize valuation for a year from now or 3 to 5 years from now? Depending on your answer, your short-term goals and actions will vary significantly. You might say your job is to drive value over the long term. But what is the long term? Should companies seek to stay in business forever at the cost of shorter-term returns?

In the early stages, to help manage this, I've found it's enormously useful to optimize around funding rounds — seed, Series A, B, C, etc. Leaders should set specific goals associated with the next raise. As an example, a team at a high-growth startup might say they want to raise their Series A in December of 2025, and by that point, they want to have:

$X in the bank
$X in revenue
$X in monthly burn rate
X% growth
X in headcount
X in number of customers
X, Y, and Z in product milestones
$X in company valuation (this one will obviously be a loose estimate based on some market-driven multiple)
X gross margin, Y operating margin (though these should be prioritized after product/market fit, burn rate, and cash are more of the focus early on)

Leadership should then be transparent with the board and investors about these metrics so everyone knows what the company is chasing. Leaders and even front-line employees should know these metrics and keep them top of mind. While this approach is far from perfect and won't align all of the different competing interests, transparency and disciplined tracking against clear metrics is a huge step forward in managing the day-to-day tradeoffs and difficult decisions that come with running a company.

Risk, Reward, And Working In Tech

Investor Alignment