Dear Sophie: How does the International Entrepreneur Parole program work?

Here’s another edition of “Dear Sophie,” the advice column that answers immigration-related questions about working at technology companies.

“Your questions are vital to the spread of knowledge that allows people all over the world to rise above borders and pursue their dreams,” says Sophie Alcorn, a Silicon Valley immigration attorney. “Whether you’re in people ops, a founder or seeking a job in Silicon Valley, I would love to answer your questions in my next column.”

Extra Crunch members receive access to weekly “Dear Sophie” columns; use promo code ALCORN to purchase a one- or two-year subscription for 50% off.


Dear Sophie,

I’m the founder of an early-stage, two-year-old fintech startup. We really want to move to San Francisco to be near our lead investor.

I heard International Entrepreneur Parole is back. What is it, and how can I apply?

— Joyous in Johannesburg

Dear Joyous,

Today for the first time, international startup founders can sigh a breath of relief because there is new hope for immigration! This hope comes in the form of a little-known pathway to live and work legally in the United States. This pathway is now possible because, effective today, the U.S. Department of Homeland Security (DHS) withdrew the proposed rule to remove the International Entrepreneur Parole Program. This development is FANTASTIC for startup founders everywhere!

DHS believes that “qualified entrepreneurs who would substantially benefit the United States by growing new businesses and creating jobs for U.S. workers” should be able to benefit from “all viable” immigration options. The National Venture Capital Association is “thrilled” at the news, and so am I!

A composite image of immigration law attorney Sophie Alcorn in front of a background with a TechCrunch logo.

Image Credits: Joanna Buniak / Sophie Alcorn (opens in a new window)

International Entrepreneur Parole (IEP) allows founders to request a 30-month immigration status, with the possibility of a 30-month extension as well. Spouses of those with IEP can qualify for work permits. There’s no limit to the variety of fields in which startups can qualify — we’ve had interest from founders in everything from autonomous drone delivery to AI for law enforcement; anticancer drug discovery to satellites.

To qualify, you need to show that:

  • Your startup is less than five years old.

3 golden rules for health tech entrepreneurs

If the last 10 years practicing family medicine have taught me anything, it’s that there is a desperate need for innovation in healthcare. I don’t just mean in terms of medical treatments or protocols, but really in every aspect. As a physician, I’ve worked with my fair share of “the latest and greatest” innovations both in my outpatient practice and at hospitals.

As I shifted into my current position, I’ve come across some products that were distinguished winners, eventually going on to become not just highly successful but the new gold standard in the industry. Others, unfortunately, never even got off the ground. Often, in the back of my mind, I felt like I could always tell which ones had the staying power to transform healthcare the way it needed to be transformed.

When it comes to ensuring the success of your product, service or innovation, following these three golden rules will put you on the right track.

When it comes to ensuring the success of your product, service or innovation, following these three golden rules will put you on the right track. It’s no guarantee, but without getting these three things right, you’ve got no shot.

Design for outcomes first

Stephen Covey coined the phrase: “Begin with the end in mind.” It’s the second of his 7 Habits. But he could have also been writing about habits for health tech innovators. It’s not enough to develop a “new tool” to use in a health setting. Maybe it has a purpose, but does it meaningfully address a need, or solve a problem, in a way that measurably improves outcomes? In other words: Does it have value?

When the COVID-19 pandemic hit, pharmaceutical and research firms set out upon a global mission to develop safe and effective vaccines, to bring the virus under control and return life around the world to something approaching “normal” … and quickly. In less than a year, Pfizer and Moderna crossed the finish line first, bringing novel two-jab mRNA vaccines to market with extraordinary speed and with an outstanding efficacy rate.

Vaccine makers started with an outcome in mind and, in countries with plentiful vaccine access, are delivering on those outcomes. But not all outcomes need be so lofty to be effective. Maybe your innovation aims to:

  • Improve patient compliance with at-home treatment plans.
  • Reduce the burden of documentation on physicians and scribes.
  • Increase access to quality care among underserved, impoverished or marginalized communities.

For example, Alertive Healthcare, one of our portfolio companies, wanted to meaningfully improve round-the-clock care for when patients couldn’t get in to see their physicians and developed a platform for clinical-grade remote patient monitoring. Patients download an easy-to-use app that sends intelligent alerts to providers, reducing documentation and decreasing time to treatment. Patients enrolled in the app reduce their risk of heart attack and stroke by 50%. That’s compelling value and an example of designing for outcomes.

When designing for outcomes, it’s also important to know precisely how you’ll measure success. When you can point toward quantifiable metrics, you’re not only giving yourself goals in your product design and development, you’re also establishing the proof points that sell your product into the market. Make them as meaningful and measurable as possible, as soon as possible.

4 lessons I learned about getting into Y Combinator (after 13 applications)

For many founders, Y Combinator is a coveted milestone on the entrepreneurial road. As of January 2021, the accelerator has helped create 60,000 jobs, has 125 companies valued over $150 million, and has facilitated top exits totaling more than $300 billion. Past alumni include Airbnb, DoorDash and Coinbase — all of which are now publicly traded.

Unsurprisingly, the program has a strict selection process — with rumors claiming that less than 5% of startups are accepted, making Y Combinator one of the most prestigious accelerators out there. Competition may be fierce, but it’s not impossible, and jumping through some hoops is not only worth the potential payoff but is ultimately a valuable learning curve for any startup.

Y Combinator isn’t bluffing when it says it wants founders to make “something people want.”

The entrepreneurs trying to get into Y Combinator are often at an early point in their journeys and haven’t yet built up the experience to know exactly what kind of business can hit the ground running. This is where a harsh journey of trial and error helps entrepreneurs face the reality of their business model. Going through the Y Combinator program’s rigorous vetting gives founders a sense-check of what they’re missing, and who they’re missing. Take it from someone who applied to the program 13 times before getting in.

Of course, 13 applications require a degree of time and money that startups don’t always have, so I’ve condensed my four biggest takeaways from the experience. Here’s how to work toward landing in the small percentage of startups successfully accepted to the Y Combinator program:

Put your business value before your personal vanity

In a sea of applications, it’s easy to feel like you have to distinguish yourself and your startup in a striking way. For me, I made my mark through an encounter with Paul Graham, one of the founders of Y Combinator — although not in the way I had hoped for.

Graham had written a lot of online essays and resources for startups. In 2012, I thought it would be great to download Graham’s essays, browse by most-used words and publish my findings on Hacker News. However, Hacker News is the social news website run by Y Combinator, and the morning after I shared my work I woke up to an email from Graham asking me to swiftly take it down.

To buy time for a failing startup, recreate the engineering process

In non-aerobatic fixed-wing aviation, spins are an emergency. If you don’t have spin recovery training, you can easily make things worse, dramatically increasing your chances of crashing. Despite the life-and-death consequences, licensed amateur pilots in the United States are not required to train for this. Uncontrolled spins don’t happen often enough to warrant the training.

Startups can enter the equivalent of a spin as well. My startup, Kolide, entered a dangerous spin in early 2018, only a year after our Series A fundraise. We had little traction and we were quickly burning through our sizable cash reserves. We were spinning out of control, certain to hit the ground in no time.

Kolide had a lot going for it that enabled me to recover the company, but by far the most important was that we recognized we were in a spin very early, and we had enough cash remaining (and therefore sufficient time) to execute a recovery plan.

All spins start with a stall — a reduction in lift when either the aircraft is flying too slowly or the nose is pointed too high. In Kolide’s case, we were doing both.

First, we raised too much money too fast. In order to justify the post-money valuation that came with the raise, we set unattainable goals. To make matters worse, we lacked the confidence in our product and strategy, so we developed our solution with hesitancy, underspending in critical areas. As a result, we were flying too steep and too slow. We stalled.

If a stall isn’t corrected promptly, a spin can develop. Flat spins are one of the worst. Once the flat spin starts, there are a number of techniques experienced pilots should perform to recover the aircraft. Nearly all of these techniques require a critical resource, altitude — or, put another way, time.

Just like amateur pilots, startup CEOs don’t receive spin recovery training. When Kolide was spinning out of control, the vast majority of the advice I received was to cut our losses and sell the company or return the money to the investors.

At the time, I didn’t find any promising examples of companies with these same problems successfully recovering; I found only smoldering wreckage. By February 2019, my co-founders departed.

Despite this tell-tale sign of imminent demise, I was ultimately able to recover and put us on track for a great fundraise. Here’s how I recreated the engineering process.

Buying time

Kolide had a lot going for it that enabled me to recover the company, but by far the most important was that we recognized we were in a spin very early, and we had enough cash remaining (and therefore sufficient time) to execute a recovery plan. Even waiting just a few more months would have likely changed the outcome.

Twitch UX teardown: The Anchor Effect and de-risking decisions

Twitch evidently has no issues getting people to spend time on its platform — even politicians can draw huge crowds by streaming themselves playing games. But monetizing video content is hard, and Twitch has missed revenue targets for the last few years.

So how does Twitch make money? And more importantly, what subtle psychology does it use within its iOS app to encourage viewers to spend more?

I’m a UX analyst and the founder of UX community Built for Mars — where I regularly tear down some of the best products in the world, showing you how they’re made, and, more importantly, how they could be improved.

I recently published my analysis of Twitch. But for Extra Crunch subscribers, I wanted to go a little deeper and bridge the gap between what Twitch does and how you can make meaningful changes to your product’s UX.

In general, you should encourage the user to make the hard decision (i.e., to commit to subscribing), after understanding all the benefits.

So here are three UX tips to discuss during your next team Zoom call.

The Anchor Effect

In short: The Anchor Effect is a heuristic bias whereby people will become attached (anchored) to an initial piece of information. For example, spending $1,000 on an iPhone may not seem like a bad deal if you saw an ad for the $1,500 one first — by comparison, it looks “cheap.”

On Twitch, when a new user subscribes to a channel for the first time, they’re shown the benefits of subscribing, and then asked how long they want those benefits for before being shown a price.

Image Credits: Twitch

This type of bias is everywhere. For example, the order of your pricing tiers will affect conversions — which is likely why Mailchimp shows its pricing tiers in reverse order.

Startup employees should pay attention to Biden’s capital gains tax plans

The Biden Administration has reportedly proposed significant changes to the capital gains tax, aiming to target the wealthiest Americans to help fund his historic aid programs.

If the current proposal goes into effect, it will have an impact on startup employees who aren’t (yet) wealthy. And it’s unlikely the Biden Administration has considered the consequences, because many of these employees aren’t yet in the highest tax bracket. But startup employees need to pay close attention to these changes when planning what to do with their stock options.

We don’t yet know what will end up in a passed bill, which may look very different from the originally proposed plan. This shouldn’t cause alarm for employees or cause them to avoid exercising options, but it is something they should be thinking about when planning their equity strategy.

When it comes to employee equity, the worst decision is always not having a plan of action.

As always, employees should work with their advisers to plan accordingly and get ahead of any changes.

How changes in capital gains tax impact startup stock options

Historically, long-term capital gains, or gains on assets held for over a year, have enjoyed preferential tax rates in comparison to short-term capital gains, which are assets held for less than a year. In Biden’s original proposal, he suggests raising the long-term capital gains rate to the highest ordinary income tax rate on income over $1 million.

If Biden’s changes are enacted, it means that there would no longer be preferential tax rates for those that make over $1 million on the sale of their shares post-IPO or as part of an acquisition. Many employees “go long” with their equity, selling them a year after exercising to benefit from long-term capital gains tax. Under this change, they may be limited to the amount of upside they can convert to preferential capital gains tax depending on their income levels and when they sell.

As with any tax legislation, the devil is in the details, many of which are still to be determined. These are the questions employees should be asking if the legislation moves forward:

  • Is the first $1 million in capital gains still taxed at preferential rates or do I factor in other sources of income to determine the $1 million threshold?
  • How can I plan around the sale of my shares to stay under the $1 million threshold?
  • Is there any impact on qualified small business stock (QSBS)?

Clarity on these questions and details of the plan will provide critical information for employees looking to exercise if Biden’s tax plan advances in Congress.

Capital gains tax rules have always been political

Many presidents have expressed interest in changing the capital gains laws in the past. President Obama, for example, wanted to raise the capital gains tax. President Trump campaigned on capital gains rules, suggesting the carried interest rules, which are possible because of capital gains tax rules, be eliminated.

The questions now are: Will Biden be successful in addressing capital gains tax rules? And will the Democrats risk backlash or potential downsides driven by increased capital gains tax? Many experts suggest that the final legislation, if passed, will result in a capital gains tax increase, but much less than Biden’s original proposal. Some are suggesting Congress will settle on no more than 30% as the highest capital gain rates for those who earn more than $1 million.

Only time will tell, but the suggested tax plan may create a significant, if unintended, burden to startup employees more than anyone else.

Planning around your equity

There’s still a lot of uncertainty around what new tax legislation may look like or if it will happen at all. At this point, startup employees may not necessarily need to act on these potential changes, but they should be taking it into account when planning what to do with their equity and, more specifically, when they are planning to exercise.

Either way, employees should still strongly consider exercising their stock options (it’s a key benefit of working at a startup, after all). Taxes are just one consideration. For example, many companies have exercise deadlines after employees leave a company.

Even if rates to capital gains taxes change, exercising early may still have its benefits, as many employees may still be able to create a plan to sell up to a certain number of shares at preferential rates every year.

While Biden’s proposed plan is focused on changing the federal tax rates, state income tax considerations remain. Startup employees have been moving away from high-tax states such as California and New York in favor of no-income tax states such as Texas and Florida. Those that are planning a move may have a big incentive to exercise their options to limit California and New York’s reach on the shares.

It’s important that employees understand the advantages and disadvantages of exercising today versus waiting until after an IPO. When it comes to employee equity, the worst decision is always not having a plan of action.

AI is ready to take on a massive healthcare challenge

Which disease results in the highest total economic burden per annum? If you guessed diabetes, cancer, heart disease or even obesity, you guessed wrong. Reaching a mammoth financial burden of $966 billion in 2019, the cost of rare diseases far outpaced diabetes ($327 billion), cancer ($174 billion), heart disease ($214 billion) and other chronic diseases.

Cognitive intelligence, or cognitive computing solutions, blend artificial intelligence technologies like neural networks, machine learning, and natural language processing, and are able to mimic human intelligence.

It’s not surprising that rare diseases didn’t come to mind. By definition, a rare disease affects fewer than 200,000 people. However, collectively, there are thousands of rare diseases and those affect around 400 million people worldwide. About half of rare disease patients are children, and the typical patient, young or old, weather a diagnostic odyssey lasting five years or more during which they undergo countless tests and see numerous specialists before ultimately receiving a diagnosis.

No longer a moonshot challenge

Shortening that diagnostic odyssey and reducing the associated costs was, until recently, a moonshot challenge, but is now within reach. About 80% of rare diseases are genetic, and technology and AI advances are combining to make genetic testing widely accessible.

Whole-genome sequencing, an advanced genetic test that allows us to examine the entire human DNA, now costs under $1,000, and market leader Illumina is targeting a $100 genome in the near future.

The remaining challenge is interpreting that data in the context of human health, which is not a trivial challenge. The typical human contains 5 million unique genetic variants and of those we need to identify a single disease-causing variant. Recent advances in cognitive AI allow us to interrogate a person’s whole genome sequence and identify disease-causing mechanisms automatically, augmenting human capacity.

A shift from narrow to cognitive AI

The path to a broadly usable AI solution required a paradigm shift from narrow to broader machine learning models. Scientists interpreting genomic data review thousands of data points, collected from different sources, in different formats.

An analysis of a human genome can take as long as eight hours, and there are only a few thousand qualified scientists worldwide. When we reach the $100 genome, analysts are expecting 50 million-60 million people will have their DNA sequenced every year. How will we analyze the data generated in the context of their health? That’s where cognitive intelligence comes in.

Freemium isn’t a trend — it’s the future of SaaS

As the COVID-19 lockdowns cascaded around the world last spring, companies large and small saw demand slow to a halt seemingly overnight. Enterprises weren’t comfortable making big, long-term commitments when they had no clue what the future would hold.

Innovative SaaS companies responded quickly by making their products available for free or at a steep discount to boost demand.

While Zoom gets all the attention, there were hundreds of free SaaS tools to help folks through the pandemic. Pluralsight ran a #FreeApril campaign, offering free access to its platform for all of April. Cloudflare made its Teams product free from March until September 1, 2020. GitHub went free for teams in April and slashed the price of its paid Team plan.

A selection of new free, free trial and low-priced offerings from leading SaaS companies. Image Credits: Kyle Poyar/OpenView.

The free products were aimed squarely at end users — whether it be a developer, individual marketer, sales rep or someone else at the edge of an organization. These end users were stuck at home during the pandemic, yet they desperately needed software to power their working lives.

End users prefer to do the vast majority of their research online before ever talking to a sales rep, making free products the ideal way to reach them.

End users prefer to do the vast majority of their research online before ever talking to a sales rep, making free products the ideal way to reach them. Many end users want to jump straight into a product, no hassle or credit card or budget approval required.

After they’ve set up an account and customized it for their workflow, end users have essentially already made a purchase decision with their time — all without ever feeling like they were in an active buying cycle.

An end user-focused free offering became an essential SaaS survival strategy in 2020.

But these free offerings didn’t go away as lockdowns loosened up. SaaS companies instead doubled down on freemium because they realized that doing so had a real and positive impact on their business. In doing so, they busted the outdated myths that have held 82% of SaaS companies back from offering their own free plan.

Myth: A free offering will cannibalize paying customers

GoDaddy is a digital behemoth, known for being a ’90s-era pioneer in web domains as well as for their controversial Super Bowl ads. The company has steadily diversified into business software, now generating roughly $700 million in ARR from its business applications segment and reaching millions of paying customers. There are very few businesses that would see greater potential revenue cannibalization from launching a free product than GoDaddy.

But GoDaddy didn’t let fear stop them from testing freemium when lockdowns set in. Freemium started out as a small-scale experiment in spring 2020 for the websites and marketing product. GoDaddy has since increased the experiment to 50% of U.S. website traffic, with plans to scale to 100% of U.S. traffic and open availability to other markets in 2021.

Beyond the fanfare and SEC warnings, SPACs are here to stay

The number of SPACs in the deep tech sector was skyrocketing, but a combination of increased SEC scrutiny and market forces over the past few weeks has slowed the pace of new SPAC transactions. The correction is an inevitable step on the path to mainstreaming SPACs as an alternative to IPOs, but it won’t cause them to go away. Instead, blank-check vehicles will evolve and will occupy a small and specialized — but important — part of the startup financing landscape.

I believe that SPAC financings can solve a major problem for all capital-intensive technology startups: the need for faster — and potentially cheaper — access to large amounts of capital to fund product development over multiple years.

The tsunami of SPAC financings sparked commentary from all corners of the capital markets community, from equity analysts and securities lawyers to VCs and fund managers — and even central bankers. That’s understandable, as more than $60 billion of SPAC deals have been announced since the beginning of 2020, plus $55 billion in PIPE capital, according to investment bank PJT Partners.

The views debated by finance experts often relate to the reasonableness of SPAC pricing and transaction structures, the alignment of incentives for stakeholders, and post-merger financial and stock price performance. But I’m not going to add another voice to the debate on the risk-reward calculus.

As the co-founder of a quantum computing software startup who worked in financial markets for two decades, I’d like to offer my perspective on two issues that I think my peers care more about: Can SPACs still solve the funding problem for capital-intensive, deep tech startups? And will they become a permanent financing option?

Keeping the lights on at deep tech startups

I believe that SPAC financings can solve a major problem for all capital-intensive technology startups: the need for faster — and potentially cheaper — access to large amounts of capital to fund product development over multiple years.

SPACs have created a limitless well of capital that deep tech startups are diving into. That’s because they are proving to be more attractive than other sources of financing, such as taking investments from later-stage VC funds or growth equity funds with finite fund sizes and specific investment themes.

The supply of growth capital from these vehicles has been astounding. In 2020, SPACs alone raised more than $83 billion via 248 IPOs, which is equal to a third of the total $300 billion raised by the entire global VC community. If the present rate of financings had continued, the annual amount of SPAC financings would have been on par with the total R&D expenditure of the U.S. government —  roughly $130 billion to $150 billion.

This new supply of capital can let startups keep the lights on, helping them address a practical need while they develop products that may take a decade to field. Before SPACs, any startup that wanted to remain independent had to lurch from one round of VC financing to the next. That, as well as the intense IPO process, is a major time sink for management teams and distracts them from focusing on product development.

For M&A success, tap legal early and often

While mergers and acquisitions may be the right strategic path for many businesses, organizations tend to underestimate the role in-house legal teams play in a large-scale strategic transaction until the company is firmly entrenched in a deal.

While the CEO and board might fully appreciate the counsel of the legal team, the ability of the legal team to earn the support of the business — from product and development to marketing and HR — is critical to a smooth, efficient closing and post-close integration process.

Your in-house legal team should be held accountable for catching things specific to your business that outside attorneys will miss.

Having been on the inside of M&A transactions, here are a few insights that I recommend any executive team considering a major strategic transaction keep in mind when working with, and setting expectations for, the in-house legal function as the deal moves from business agreement to closing and through integration.

Is this the right transaction to move the business forward?

When you’re thinking of M&A (or any other type of strategic transaction, for that matter), it is critical to understand why you’re pursuing a deal and what the potential implications (both good and bad) may be for the business at large.

As the executive or founding team, have you agreed that doing the deal is the best way to further the overall strategic business objectives? Is the proposed deal allowing the company to scale more rapidly or efficiently? Does the transaction provide for a more diversified, complementary product offering?

After settling that the deal is the best way to achieve the overall business objective, the next focus is on execution. How will the resulting leadership bring together the two organizations? Do you have a plan on how to go from closing the transaction to successfully moving forward with the strategic purposes for doing the transaction in the first place? Is there agreement on product direction, go-to-market strategies, staffing, company culture, etc.?

These high-level discussions are important to have while evaluating a potential deal, and bringing in your internal legal leadership is critical in these early phases. You may identify during these early discussions aspects that are critical for the deal to be a success, and being sure your legal team is aware of these aspects allows the team to anticipate post-closing issues and resolve them proactively with the structure of the deal or by explicitly calling out critical obligations of each party.

Your in-house legal team should be held accountable for catching things specific to your business that outside attorneys will miss. Outside attorneys are experts in M&A or IPOs or venture financings or whatever else, but your in-house lawyers are experts in your company — that’s the true value of having an in-house team.