2019 saw a stampede of fintech unicorns

Two years ago, we created the Matrix FinTech Index to highlight what we saw as the beginnings of a 10+ year mega innovation wave in financial services.

The trillion-dollar financial services industry was going to be turned on its head over the next decade, and we were just getting started. At the time, the top 10 publicly traded U.S. fintech companies had just surpassed the $100 billion mark in terms of total market capitalization, 12 unicorns had emerged in the category, and the U.S. VC industry had just poured in $6.7B — a record at the time.

As we predicted last year, the innovation cycle continues, and we are transitioning into its mid-phase. So what happened in U.S. fintech in 2019? In short, monster growth.

On the public side, fintechs delivered resoundingly. PayPal alone gained $26B in market capitalization. On a return basis, the public Matrix FinTech Index continued to crush every major equity index as well as the financial services incumbents. Nicely matching our forecasts, our Index delivered 213% returns over the last three years. The Index outperformed the financial services incumbents by 151 percentage points and the S&P 500 by 170 percentage points.

Deciding how much equity to give your key employees

Anu Shukla had found the perfect VP of Engineering to help her build her latest startup, a company called RewardsPay. By that point, she had founded or cofounded several venture-backed startups (she’s up to five). The standard, she knew, was a roughly 1.5% to 2% stake for a key employee at the executive level.

But Shukla knew sometimes you need to give up more to get the right person. “At that point, there wasn’t much cash in the company,” Shukla says of RewardsPay, the company she founded in 2010 to help consumers convert rewards points into a commodity they could spend elsewhere. “This is the person we were asking to come in and build the technology and build our technology team,” she adds. He was also someone with experience who could command a sizable salary from a more established company.

Shukla ended up giving him a 3% equity share in the company. He needed to remain motivated to stick around for the long-run, Shukla explains, “and we also knew through subsequent rounds of funding he would become diluted.”

Tech’s main currency is built on a range of factors

Equity, typically in the form of stock options, is the currency of the tech and startup worlds. After dividing initial stakes among themselves, founders use it to lure talent and compensate employees for the salary cut that they almost inevitably will take when joining a startup. It helps keep employees motivated with the tantalizing prospect of a big payday when the company is sold or goes public.

But how much equity should founders grant the first engineers hired to help them build their product and the new hires that follow? What about that highly coveted VP of Sales brought on once a company has a product to sell? And what about others a young startup seeks to enlist in the cause, including key advisors whose insights and connections might increase its chances of success or perhaps an outside director with the right expertise to join a nascent board of directors?

Properly parceling out equity is a challenge for first-time founders. What stake an employee deserves depends on a range of factors, from skills to seniority and employee badge number.

“Is this employee #5 we’re talking about or employee #25?” asks serial entrepreneur Joe Beninato, who has founded or cofounded four startups and worked at another four. “What’s the experience of the person coming over? You have to look at each situation individually.”

1% or .05%? It depends on position and seniority

Yet while complex, several online guides provide compensation benchmarks that help founders think about the size of each slice of the company they give away when recruiting talent. Index Ventures, for instance, has published a handbook aimed at helping entrepreneurs figure out option grants at the seed level. At a company’s earliest stages, expect to give a senior engineer as much as 1% of a company, the handbook advises, but an experienced business development employee is typically given a .35% cut. An engineer coming in at the mid-level can expect .45% versus .15% for a junior engineer. A junior biz dev person should expect .05%, which is the same for a junior person coming in as a designer or in marketing.

And just because someone gets a big title, it doesn’t mean you should give away the store. “We see a lot of role and title inflation going on at the seed stage, which is best avoided,” warns Reshma Sohoni, co-founder and general partner at Seedcamp, a European seed fund quoted in the Index handbook. “At this stage, you are unsure of who is going to continue the adventure with you.”

Timing trumps seniority and experience

When Shukla was building her team at RewardsPay, she gave the earliest engineers joining her team an equity share of between .5% and 1%, depending on both experience and a person’s salary requirements. Some were willing and able to work for a minimal salary and higher equity, whereas others asked for higher cash compensation because of their personal circumstances. Regardless, Shulka says, “the early team you put together definitely gets a lot more stock than later employees.”

Indeed, in many circumstances, the timing of an employee’s decision to join has a disproportionate impact on how much equity is offered. It makes sense: the earlier someone commits to your startup, the more risk the hire is taking on.

If a key hire is the third person joining a two-person team, he or she can almost be considered a co-founder and may get as much as 10% of the company. But if a head of sales or VP of marketing joins once a startup has a product to sell and promote, they may get between 1% and 2%, depending on experience.

“The percentages really vary dramatically,” Beninato says. “I don’t want to say it’s like a decaying exponential, but it’s something like that. The first people get more, and it goes down over time.”

Time for an employee option pool

Eventually, founders need to think about creating an employee option pool — a more disciplined way to award equity over shaving off more shares with each new hire. “After a seed round, you want to have that employee pool at around 10% or 12%, plus or minus,” says James Currier, a four-time founder who is now a managing partner at NFX, an early-stage venture capital firm. Calibrating the precise size of that option pool, Currier and others say, depends on a company’s hiring ambitions over the coming 12 to 18 months — through a next funding cycle.

Again, online guides can help. The Holloway Guide to Equity Compensation, for instance, is an 80-page handbook that explains arcane terms such as “cliffs,” “claw backs,” “single trigger” and “double trigger” that any entrepreneur must know to even understand what their lawyers and advisors are telling them. The guide also identifies landmines to avoid and breaks down the equity ownership of a pair of sample companies whose employee pools range from 9% to 20%.

Over time, founders will need to tinker with the option pool as everyone’s shares are diluted with each venture round. “After an A, you want to put it back to 10 to 15%, depending on how many managers you need,” Currier says. Adds Anu Shukla, “Usually, the VCs are going to ask for a completely empty option pool where every share is available.”

Prepare to negotiate

The size of the option pool must be part of the negotiations with any venture capitalist — and founders would be wise to have thought about the issue before sitting in a VC’s conference room. “VCs often sneak in additional economics for themselves by increasing the amount of the option pool on a pre-money basis,” warn Brad Feld and Jason Mendelson in their book, Venture Deals: Be Smarter Than Your Lawyer and Venture Capitalist. At that point, the option pool is coming from the founders’ shares and those of their earliest investor so Feld and Mendelson encourage founders to push back if they feel the VCs are asking for an unduly large option pool.

“The entrepreneur can say, ‘look, I strongly believe we have enough options to cover our needs,’” Feld and Mendelson advise. To protect the VCs, they say, offer full anti-dilution protection in case the founders are wrong, and they need to expand the option pool before the next financing.

No one gets everything at once

Equity awards, regardless of their form, are subject to vesting schedules. Traditionally, startups have used a four-year benchmark with a one-year cliff: no ownership until an employee has worked twelve months, and then 25% for each year worked (or an additional 1/48th for every month worked). Yet there’s also the growing recognition that building a successful company usually takes a lot longer than four years, and options are about retaining people to build something great. As a result, longer vesting schedules are becoming more commonplace.

The growing time it takes companies to go public or be acquired is also affecting other stock option terms. Typically, employees have had up to 90 days after leaving a company to exercise their options, which can be costly and come with a large tax bill. Now companies are sometimes extending that period well beyond 90 days so that an employee won’t end up with nothing if they leave long before they can turn their equity into cash.

Boards of advisors and directors

Equity is also suitable for drawing a different kind of talent to your company: experienced people in the field who won’t come to work for you full-time but, if their interests were aligned with yours, might serve as advisors who increase your chances of success. (At this stage of a company, non-founder board members are likely to be its investors, so their equity will be commensurate with the size of their investment.)

Currier, the serial entrepreneur turned venture capitalist, says he typically offered between .1% and .3% of the company to attract an advisor to one of his companies. “What you’re hoping for is that one advisor who tells you something that triples the value of your company,” he says. “The problem is you don’t know which one of the five or six people you’d brought in as advisors will be that person. So you pay them all .2% and hope one gives you that idea that more than pays for itself.”

The takeaway: cash is limited, but so is equity

Giving out equity may feel painless. After all, it’s an easy way to preserve your cash as you staff your startup with top-notch hires that can significantly increase your chances of success. But take the time to understand the value of what you’re giving away, and bring discipline to the process early by creating an employee pool. Then if you have to spend a little extra to get someone really exceptional, as Shukla’s RewardsPay had to do, you’ll know where you stand.

How startups fill the gap between revenue and investment

I get tons of inbound from entrepreneurs and founders, from first-timers with an idea to CEOs with millions in annual revenue, and they all ask what basically boils down to the same question:

“I’ve taken my startup this far, how do I get the money to take it to the next level?”

In 20 years of building companies, roughly half of our companies have taken some form of investment to go after a much larger payoff than our existing revenue would allow. It wasn’t something we celebrated, it was something we felt was mandatory. In other words, there was no other way and outside funding became our best hope.

When you have revenue and you chase funding, you should know what you’re getting into and you should exhaust every other avenue before you decide that someone else’s money is a better bet than your customers’ money. 

Remember: the easier the path, the lesser the payoff. 

The easiest path: venture capital funding

I know it’s heresy to talk about how easy it is to raise money. It’s actually not, and I’ll be the first to admit it: your odds are poor, it’s going to take all your time and energy, and you’re going to be beholden to a bunch of people who have a different vision of your idea than you do.

But if you need scale money, this is the only shortcut.

Now, I say “scale money” because you should only be seeking VC money to scale your business, not establish it. The odds of getting funded for an idea with no current revenue and no current growth are infinitesimally slim. 

So let me start with some truth for the earliest of early-stagers. You’re going to have to walk a harder path, so keep reading.

If you do have revenue, the first thing you have to show a VC associate, the gatekeeper of the firm, is how your existing revenue is going to grow 10x to 100x over the next three to five years. This is standard VC math. 

I’ll leave it to others to debate the logic and/or fairness of the process. My point is that you can put any multiplier you want on zero revenue and the result will still be zero. Even if you’ve got $1,000 in monthly revenue, then that’s about $10,000 in annual revenue, and at best, at 100x, the investor is thinking you might be worth $1 million if all the stars align. 

Most VCs won’t touch a valuation that low unless you’ve got a track record. If you don’t, you’re kind of wasting your time putting a deck together. 

Don’t waste your time. Your startup is probably better than that. You just need to prove it.

The not-so-easy-path: find a rich person

Dear Sophie: what do I need to know about recent changes to the H-1B lottery?

Today, we’re launching “Dear Sophie,” an advice column that answers reader questions about immigration, particularly with regard to the tech sector.

“My goal is to help people understand immigration laws in a way that lets them overcome borders and pursue their dreams,” says Sophie Alcorn, an immigration attorney based in Silicon Valley. “I believe every question (and answer) helps bring clarity to many and would love to feature yours in my next column.”

Future “Dear Sophie” columns will be accessible for Extra Crunch subscribers; use promo code ALCORN to purchase a 1- or 2-year subscription for 50% off.


Dear Sophie: I lead People Ops for an early-stage enterprise SAAS startup. My company is giving me the green light to hire internationally, but I’ve never gone through this process. I’ve heard there have been some changes to the H-1B lottery. What do I need to know to get started?

— Curious in California

Dear Curious:

Congrats! Glad to hear your company is taking this step — it’s great for the success of your company, and it’s awesome that you’re helping them take on this important challenge. I’m super excited about the changes to the H-1B lottery this year because they are going to benefit early-stage startups quite a bit.

For some context: in the past, it was cost-prohibitive for small companies to invest in preparing an H-1B petition package for a potential hire. There was no way of knowing in advance if a candidate would beat the lottery’s odds and be the one person chosen out of every three applicants. Starting in 2019, candidates with advanced degrees from American universities received an extra bite at the apple, but that still didn’t mean it was a sure thing.

For the upcoming round, the government is adopting an electronic registration system. This change is great for small businesses because you don’t have to invest in legal fees to prepare H-1B petitions until you know that your candidate was already selected and has the opportunity to apply.

As you probably already know, an H-1B is a nonimmigrant visa that lets professionals with bachelor’s degrees or equivalent work experience in specialized fields (such as science, IT, medicine, accounting, law, engineering, mathematics, etc.) gain employment with an American company. This employment needs to be for positions that require their level of expertise at companies that have the budget for their resources.

Most of the requirements for the H-1B visa are set by law, but the details do change once in a while. The government hosts an annual lottery because there is a statutory cap on the total number of new H-1B visas allowed every year, and recent demand outweighs supply.

The government just announced that the lottery format is changing. Here’s what you need to know about the upcoming changes to the lottery, most of which will take effect in Q1 and Q2 of 2020 for jobs starting as early as October 1st, 2020:

  • There will be a new electronic registration system with a $10 non-refundable fee:
    • register online between March 1 and March 20, 2020 to participate; don’t miss this window!
    • fees will be $10 per candidate;
    • the government will select candidates after the initial registration period ends and no later than March 31, 2020.
  • Companies can then file H-1B petitions for anybody who was selected.
  • There will be a 90-day window to submit completed petitions.
  • Upon filing, your company will be required to pay the standard applicable government filing fees (usually roughly $1,500-3,000 for small companies).
  • Premium processing is currently available for an optional $1440 extra. The government will take action within 15 calendar days if you use this option. We’ll see if this option remains available.

There’s a lot of great information out there on the H-1B visa and status, but it’s been under strict scrutiny lately — especially in tech lately. I recommend contacting an immigration attorney for guidance early before the registration window opens.

When People Ops folks like you reach out to me, they want to know how to start preparing now. Here are my most common tips for early-stage startups:

Ask employees and candidates seeking H-1B to gather their documents (such as transcripts, diplomas, resumes, past immigration documents, etc.) as early as possible. I also recommend talking to an attorney to determine if they’ll need education or experience evaluations and if so, getting them done early.

I also recommend they do the following to prepare their early-stage startup for success:

  • ensure that the company’s FEIN Number has been validated with DOL (ask an attorney for help)
  • choose the proper job title with the guidance of your immigration attorney
  • brainstorm the corresponding job duties/description
  • gather the necessary documents from your company
  • take screenshots of your company’s website
  • put together a portfolio of your company’s marketing materials
  • have the company’s latest pitch deck ready to share
  • make sure the company’s taxes are current and you have the returns

As you can see, there’s a good amount of attention to detail required from you, but with some time and a legal team to support you, you’ll do great.

Bringing the best talent to your company benefits everyone involved and is important work. I wish you the best as you begin this process and encourage you to reach out if you need a little help!


Submit your questions to immigration attorney Sophie Alcorn here; all questions will be answered confidentially.