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Video interview from CREtech NY 2022: Why now?

Here is a short (~7min) video interview I gave at CREtech NY 2022* covering two “Why now?” questions:

  1. What are the key factors that contribute to today’s unique investment landscape and why now is a golden opportunity corporate venture
  2. How startups can answer “Why now?”and why that question is crucial for VC and angel investors.

* this time the delay in posting is not my fault. They just published the clip on Jan 3

Video interview: How a CVC Can Power Innovation in Real Estate Technology

Here is a short (~9min) video interview (of me) from Blueprint 2022 covering, among other things, how CVC can power innovation in Real Estate … IFF done right… and why so many times it isn’t.

(the delay posting this is entirely my fault – they got the clip to me weeks ago.)

Already excited for Blueprint2023!

Blueprint 2022 Panel: How To Do CVC Right

Great panel discussion at Blueprint 2022 with Kyle Beatty (AmFam Ventures) Momei Qu (PSP), and Elie Finegold (Crow Holdings) covering many of the common pitfalls of Corporate Venturing and solid advice on how to do it effectively and to maximize the value of the corporate parent to the startup and vice versa.

How Family Offices & Real Estate Firms Can Source Great Proptech Opportunities

Note: This article first appeared the Fall 2020 edition of Family Office Real Estate Magazine.

FORE Magazine logo

Publisher’s Insight: For years now, I have been a big supporter of property technology or “proptech.” It is an area that will change and disrupt the industry, mainly because the industry is so fragmented and because it is one of the sectors that typically lag other sectors due to the nature of the business. This article is insightful and helpful in identifying some of these opportunities, primarily because this is the future of real estate.

Many family offices that invest in real estate property startups (“proptech”) are real estate operators with reasons for investing from strategic insights to benefit their assets. For the family office that is heavily invested in real estate, the case for investing in proptech startups or Venture Capital funds is doubly strong.

But it is much easier said than done. This scenario is quite typical:

  1. A family office with real estate roots decides to find great startups to invest in or partner with.
  2. Someone, usually from the younger generation of the family, with a fair amount of real estate knowledge, but virtually no startup experience is tapped to lead the charge.
  3. Once the word gets out of the interest in investing in proptech companies, they are bombarded with startup and fund pitches, not to mention a host of investment advisors.
  4. Many of these investments are not even proptech, but enough are that he or she spends tons of time wading through pitch decks.
  5. A few of these startups look pretty good, so the family office decides to invest and/or set up pilot projects with the operating company.
  6. These fail miserably.
  7. The family office decides that engaging with startups is a waste of time.

There is, however, a better way to go about this.


As the Cheshire Cat told Alice, “If you don’t know where you are going, any road can take you there.”

If the goal is to partner with a proptech startup to get a leg up competitively or even if the operating company vets the startup’s solution, you need to be looking at startups at the right level of maturity. This means looking for startups raising Seed ($1M-$2M) or, to be safer, Series A ($4M- $8M+) rounds.** Earlier stage startups are still cocktail napkins and science projects; the later stage isn’t cutting edge. The founders are also less experienced, and the product is still a bit raw, so while it’s tempting to want to get in earlier (and you can write smaller checks and still be a player), you probably want to start with the slightly more mature guys. This filter, by itself, will weed out many startups and save tons of time.

* * Important note: you would not be investing this amount in the startups. The lead investor will generally fund half or more of the total investment round. A family office participating in the round would likely invest 10-25% of the whole round. An investment of this size would equal roughly $100K-$500K+, depending on the round’s size.


In-depth domain knowledge isn’t enough. You wouldn’t let someone with no development experience pick real estate assets to invest in, so why would you let someone with no startup investment experience pick startups? You need to pair up the industry experience with the VC skills. Fortunately, it’s possible to find people with 5+ years of venture experience and at least some proptech investment experience. It is those investors who will ultimately want to raise their venture funds. If approached with this kind of opportunity, they will look to invest in 10-20 startups over the next year or two with the expectation that, if all goes well, you would jointly look to bring in outside money to turn this into a formal VC fund. To give you a sense of what this translates into financially, assume that you are focusing on (relatively) more mature startups raising Series A rounds (average $5M) where you are committing to 10% of the round (average $500K check size), so for 10-20 investments, this comes to a $5M-$10M commitment.

As an alternative, some family offices invest in a proptech VC fund to get early access to a range of portfolio companies. Depending on the size of the fund. It will generally want a $1M-$5M investment (technically, a “commitment”) to be called over 4-6 years. With a smaller investment, an investor would not necessarily have access to as many proptech startups. The exception would be if an investment were made into multiple funds.) A downside would be you would most likely not receive the same insights into the rapidly evolving real estate world you would otherwise get from investing directly.

Often you need someone with more than just a proptech VC experience. Many investors with real estate operating companies use the business line to help assess how well a startup’s product or service fits the market; in some cases, their entire purpose of investing in proptech startups is to find innovation for their own real estate business. If piloting with the parent company is vital to your strategy, then having your business units work with the startup for some time (viz., a “pilot” or trial project) is critical. It would help if you had someone who can work internal politics. You can’t pilot with startups if you don’t know who in the line is genuinely interested in innovation instead of just paying lip service to it: you need someone who can work internal politics. This is not part of the typical VC experience, so you have to look at the candidates’ backgrounds for other indications. Prior experience at large companies (including consulting), business development work, a stint at an accelerator, etc. are all some clues that a candidate might have the right political antenna.


Having third parties bring you deals in exchange for a commission is entirely normal in the real estate world. This could translate into a kiss of death in the venture world; the best startups are never represented by an investment advisor.

VCs are the most networked people on the face of the earth. VC professionals present at panels or judge pitch events all the time. They meet dozens of entrepreneurs every week and know – and have often co-invested with – virtually every other VC in the same space. If a founder can’t network into a warm introduction to a VC, how will he find customers? Plus, the very fact that the founder thinks he can wave his hand and have someone else take on something this crucial to his business for him is a huge red flag. Those startups are invariably hairy, old, over-shopped deals that every halfway serious investor has already turned down.


When you get a startup’s pitch deck, the temptation is to read it all, think about the business as a whole, and come to a holistic, well-reasoned thesis. That kind of deep-dive takes much time, and there are many startups to review. The startup needs to earn that much of your time. Your first pass review should be much quicker, just a few minutes, to filter out startups that can’t make the cut. It takes time, domain expertise, and much deal flow to build the kind of pattern recognition that lets you immediately filter out the proptech startups that are too early or too fatally flawed to be worth the extra time.


There’s a saying in business: You get what you measure.

Do you measure the number of startup pilots a division undertakes? Is this a factor in whether a manager gets promoted? If you do track pilots, how do you track them?

One of the more subtle mistakes companies makes a focus on success. In most cases, a failed project is a black mark that can cost a manager their bonus and promotions. If a project isn’t performing, the manager will often throw more resources at it until they can claim some victory, delaying resolution, and wasting time and money.

Instead, the focus needs to be on learning quickly. Pilots should explicitly be for 3-6 months, and the questions should telegraph that even negative results are a win, as long as they get there quickly, and the results are actionable. To make this a bit more concrete, here are a few examples:


  • “It’s been three months; what have we learned so far? What actions should we take?”
  • “Have we learned enough, or do we need another three months?” What specifically would we learn if we extended?”
  • “What would teach us more and generate more actionable results: extending this pilot or moving on to the next one?”


  • “We’ve tried syndicating XYZ deal on a real estate blockchain exchange but didn’t get any qualified investors.” (Close this pilot and try something new.)
  • “We proved that we could charge an $$$ per month premium for smart apartments, but the product itself was buggy.” (Is it fixable, or should we ditch this startup and pilot with a competitor?)
  • “Our tenants love the amenity portal, and the software seamlessly coordinates access for the dog walkers, fitness pros, cleaners, etc. with the front desk. Plus, the founders are a pleasure to work with.” (Stop the pilot and roll out more broadly.)


For the family office with significant real estate assets, investing in proptech startups is not just a financial opportunity; it is also a strategic opportunity in many cases. But it is much easier said than done, and how you do it and whom you pick to do it for you to make a huge difference.

Accessing Innovation: So You Think You Want To Set Up A Corporate Venture Fund

Note: This post was previously released as a series of articles in BUILDER Online, Architect Magazine, and MULTIFAMILY EXECUTIVE published August through November 2019.

Part 1: What’s the value in a corporate venture fund?

Setting up a corporate venture capital fund (“CVC”) can be one of the most efficient and effective ways to attract external innovation to a large enterprise. Done wrong, it can also be a colossal waste of money, brains, and time.

Unfortunately, it is typically done wrong.

Returns data for CVCs is notoriously difficult to compile, but according to unpublished data by Correlation Ventures, which includes data from DowJones VentureSource as well as other primary and secondary sources, dollar-weighted (by round size), realized, cash-on-cash multiples for all U.S. venture financings in companies exiting (viz., out-of-business, acquired, or IPO) from 2008 through 2017, were 2.2X for all financings, as compared to 1.8X for all financing with at least one corporate VC participating.

The difference in returns gets less pronounced the later the stage but persists across all stages. In other words, the earlier the round, the worse CVC investments do relative to deals with no CVC.While financial data is hard to get, innovation sourcing efficacy is effectively impossible to measure. That said, anecdotal data points to higher staffing turnover and higher than normal fund closure rates for CVCs as compared to traditional VC, all of which imply that the parent corporation is not satisfied with the CVC as a vehicle for sourcing innovation either.

So while a CVC should, in theory, be a fast, cost effective, way to access cutting edge innovation, all too often they move slowly, make mediocre investments, and miss out on the hottest deals.

The reasons for this fall under two general categories. Let’s break down what goes wrong… and how to do it right.

Failure to function effectively as a VC fund

  • Inability to attract high quality venture professionals due to inadequate incentives
  • Corporate executives improperly involved in the process
  • Investment funds incorrectly allocated

Failure to integrate effectively with the corporate parent

  • Target startup investment stage not matched to corporate capabilities
  • Allocation strategy suboptimal
  • Startup sourcing strategy fails to play to parent corporate’s strength
  • Engaging the corporate organization at the wrong time
  • Passively assuming that innovation will be received by the corporate parent

Failure to function effectively as a VC fund

  • Inability to attract high quality venture professionals due to inadequate incentives

The rap on CVCs is that they are for people on the way up or the way down. The newly hired general partner is either an up-and-coming star looking for a good platform before raising his or her own fund or someone with a failed fund who is looking for a soft landing. While an overgeneralization, there is a kernel of truth: why would anyone who could raise their own fund put up with corporate politics?

So how can a corporate snag a rising star versus a falling one? It can start by replicating traditional venture fund economics so the best talent doesn’t opt out. When JLL set up their $100M CVC fund JLL Spark, they were careful to set it up as an independent fund, giving the general partners the same kind of carried interest they would get if they were running their own fund.

Farsighted corporations think even further ahead: If the first CVC fund does well, the general partners will want to raise a second, likely larger fund, and will naturally be tempted to go out on their own. A savvy corporate will not only expect this but will encourage it by being the lead investor in the second fund while allowing the general partners to bring in outside money to make the fund even bigger. As long as the money doesn’t come from a direct competitor – unlikely in any event – the corporate sponsor should be thrilled: they get more firepower for the same investment on their part.

In addition to structuring Toyota AI Ventures as a standard “2-and-20” VC fund with Toyota Research Institute as the sole LP, Toyota has structured this fund as a template that other Toyota business units can use, either solely or with outside LPs, for their own CVC funds.

Part 2: Corporate executives wade into unfamiliar territory

Because senior management may have a deep understanding of the sector and the specific needs of the corporate sponsor, it seems easy to assume that involving them in the selection process will help the corporate venture capitalist (CVC) pick the right startups to support? However, that’s not the case. I’ll explain.

As part of due diligence, a skilled venture capitalist confirms market demand by talking to a startup’s potential customers. Sector-focused investors can quickly get a feel for what customers in their sector are interested in and what they are leaning into from an investment standpoint. So, at least for a first cut, involving management in the selection process is not necessary.

Not only is it not necessary, it actually can lead to worse decisions. One of the main reasons to set up a CVC is to help its mid- and senior management recognize innovative startups, access them, interface with them, and absorb that outside innovation. So why expect them to be good at it from day one? In practice, inexperienced innovation teams often spend too much time engaging with immature or—to the eyes of a skilled venture capitalist—obviously fatally flawed startups. They waste time, money, and, worst of all, the attention of the business lines, souring them on startups in general.

Once the CVC has winnowed out 9 out of 10 (or 19 out of 20) potential investments, there’s definitely a place for the line management to vet the solution in greater depth… stay tuned for another in depth look at this topic in another part of this series.

How is fiscal oversight managed? When a corporation allocates $50 million or more than $100 million to a project, it is only natural that they want oversight. In this case, it often means that senior management wants to sit on the investment committee and approve investments. But these senior managers often run multi-hundred-million dollar divisions where their “day jobs” always come first. Asking them to find mutually convenient time to meet to review a $1M deal is a recipe for delay. Plus, when a fund has a reputation for moving slowly, the hot deals pass them by.

A smarter balance between speed, flexibility and oversight is to allow the CVC to make routine investments, subjecting only especially large follow-on investments for approval by senior management.

In theory, investing off the balance sheet from budgeted funds should be as effective as committed capital within a formal venture capital fund structure. In practice, it rarely is. Budgets get cut, routine approvals become bargaining chips for corporate horse trading, investment committee members push for pet projects, in addition to potential acqui-hires (hires through acquisition). Creating an arm’s-length contract that obligates them to meet capital calls and also creating governing documents that clearly establish the fund’s mandate and general partners’ sole authority to make investments, up to a certain threshold, insulate the CVC from these pressures, empower it to operate on par with traditional venture capital funds, and enable it to attract top talent.

Another more subtle reason for an arm’s-length fund commitment is to avoid failing by success. When a venture team has a large exit that makes the partners some of the most highly compensated people in the company, there can be a lot of pressure from line management to renegotiate that deal. Since salary is easier to cut than carry, top venture capital talent often shy away from CVCs.

But structuring a CVC to be able to function as effectively as a traditional venture capital fund is only half the battle. The best startups have their pick of investors. How does a CVC make it so that it is a hot startup’s top pick?

Part 3: Making good with the corporate parent

Structuring a corporate venture capital (CVC) to function effectively as a venture capital firm (VC) is only half the battle. Even phenomenal VC returns often amount to a mere rounding error on a Fortune 500 company’s financial statements. So if the CVC doesn’t meet the strategic objective of injecting innovation into the mothership, it is a failure regardless of returns.

At the same time, there is a lot of venture money out there chasing great startups. So how does a CVC mobilize the corporate sponsor as a unique competitive advantage over other VCs?

Fortunately, the same plan solves both problems.

In most cases, a CVC should be investing at the seed or series A round stages. If they approach investment at an earlier point, the startups are still basically cocktail napkins and science projects; any later, they aren’t at the cutting edge of innovation. If an organization is good at working with the earliest stage startups and patient with founders who are still figuring out how to work with large corporations, engaging at the seed stage yields the most exposure to innovation for the buck. Unfortunately, very few corporations meet this description.

Most corporations have little or no structural process for introducing startups to the business lines and provide little or no training to line management on how to work with entrepreneurs. In these situations, working with entrepreneurs who have some experience making corporate pilots work significantly increases the odds of success.

Now let’s take a look at how to optimize the allocation strategy. A typical Series A round in New York City is currently somewhere between $4 million and $8 million. So funds in that stage are looking to make initial investments of more than $2 million, if they want to lead the round, down to as little as $500,000, if they are following a lead. Most VC funds want a mix of deals to lead and follow. After all, if they don’t lead some deals, why would other VC funds syndicate their deals to them? So, it is safe to assume an initial average $1 million check. Assuming also that a fund would like to make at least 10 investments a year over the three-year initial investment, that would add up to $30 million for initial checks. Furthermore, most funds like to reserve about half their fund for follow-on investment. This implies that $60 million is the ante for a traditional series A VC fund, which would also yield 30 portfolio companies.

A CVC is tasked with maximizing its exposure to innovation, so what are some ways it can get more shots on goal for the same or less committed capital? For one thing, it might not need capital for follow-on investments. While the general partners of the fund would want the dry powder to make these investments in order to maximize their ROI, follow-on investments don’t increase the corporation’s net exposure to innovation. So a CVC could have zero reserve for follow-on investments and opt to invest off the balance sheet on an opportunistic, case-by-case basis. This means that a CVC could get exposure to the same 30 portfolio companies with just a $30 million fund.

Remember, though, that attracting top investment talent to the CVC is critical. So to align incentives with the general partners, if the corporate sponsor does invest, the general partners get their usual carry on that investment; if it does not, the pro rate investment rights revert to the general partners to syndicate in any way they see fit.

But what if the CVC found a way only to follow on rounds that other funds lead? In that case, the initial check size drops to $500,000 and that same $30 million fund now gets 60 shots on goal. So how do we pull that trick off?

Part 4: Target startups to leverage your corporate strengths

All too often, a corporate venture capital (CVC) will over-negotiate from a position of strength and demand nonstandard terms. For example, a CVC may demand a right of first refusal on sale. From the corporation’s perspective, this is a reasonable way for them to protect their innovation advantage. From the startup’s perspective, this deters other buyers from bidding on their startup, the startup is limited to extend resources if the corporation can exercise a right of first refusal. Senior management may also seek to block the startup from selling to competitors, limiting the startup’s ability to grow. At best, these demands slow the process down; at worst, they kill the deal… or the startup.

Instead of over-negotiating from a position of strength, a CVC needs to take the startup’s prospective and structure a strategy that plays to the corporate parent’s strengths.

What do all startups need more than anything else? Customers! A CVC has unique and unfair advantage over traditional VC funds in this respect. Done properly, they can introduce a portfolio company into the organization, generating not only significant revenue but also meaningful proof points that will make the startup itself more investable overall. A smart startup makes room for strategic investors like this.

This means that a “follow-only” strategy may be a viable option for a CVC. Consider this value proposition to a startup, which you can get in writing with either a carefully constructed, but not over-lawyered, Investor Rights Agreement or warrant coverage:

“We will get you a pilot within the organization. If the pilot goes well, we will hard-commit to invest $500,000 in your next round*, as long as it is led by an institutional VC fund. If we cannot get you a pilot or if the pilot does not go well, we will not invest.”

It’s clear, it’s concise, and it’s compelling. Climb a hill, plant your flag, and start yelling it from the mountaintop. Startups will come to you.

No capital allocated to follow on investment lets the CVC halve the required fund size from $60 million to $30 million. A pilot-to-invest strategy that only a CVC can deliver on, enables it to double the number of startups it can invest in out of that same half-sized fund.

How do you engage at the right time? The above strategy only works, however, if the CVC gets the timing right. If the CVC engages too late and the startup raises its series A round before the pilot is complete, the effort is lost.

Pilots within a large organization can take six months (or more) to connect, structure, execute, and evaluate. CVCs need to understand what a reasonable timeline is for their organization and then target startups at the appropriate time. Engaging with startups three to six months after their seed round gives them time to complete the pilot nine to 12 months post-seed, which generally coincides with when the startups are beginning to raise their series A.

Part 5: Manage the innovation process

Through this series, we have focused on maximizing the quantity of innovation that a corporate venture capital fund can deliver to the corporate parent. But, where otherwise effective CVCs often fall down is in assuming that bringing an innovative startup to the organization will automatically result in pilots and innovation transfer. Line management is busy running their own business units. After the initial flurry of focus, engaging with startups is typically nowhere near the top of their priority list.

There are two basic strategies for aligning focus so as to maximize a large organization’s exposure to innovation and to accelerate the CVC portfolio’s growth:

Informal – Someone affiliated with the CVC works hard to develop personal relationships with key decision-makers throughout the organization. This person gets to know who is serious about and amenable to working with startups to find innovative solutions to problems and who is merely paying lip service to the creed. He or she uses a bit of salesmanship, some moral persuasion, and the knowledge of the possible to make pilots happen. This approach requires minimal change to the corporate parent and can be implemented the fastest. The disadvantages are that it takes a very skilled person to pull this off and that, in many cases, the fund will have to pass on startups that really could make a difference to the parent organization simply because they are not able to convince anyone within the corporation to conduct a pilot.

Formal – This involves creating a series of structures designed to involve mid- to senior-management in the innovation ecosystem. This includes but goes far beyond simply scheduling pitch events throughout the regions where the corporate parent operates. To be truly effective, management’s job requirements and compensation structure have to change. While the possibilities are endless, here are a few examples:

  • Incorporating into six month and annual reviews metrics quantifying how many pilots a business unit attempted. Avoid over-emphasizing pilot success – that ends up deterring experimentation. After all, several quick-and-cheap failed pilots are also valuable.
  • Setting up a standing committee of senior management that meets once every few months under the guidance of the CVC to identify one or two key areas of innovation (e.g., smart apartment technology for a REIT holding multifamily rental properties) that they want to be the CVC’s primary focus at that time. This has the added benefit of effectively pre-committing the business line to piloting with the startup (or startups) that the CVC finds.
  • Requiring all middle management to evaluate prospective startup investments using a simplified scoring rubric designed by the CVC. Innovation is infectious; expose someone to 20, 30, 40+ groundbreaking startups and they will catch the fever. (If they don’t that tells you something about that manager….) Plus, when one of the startups they reviewed favorably is selected, they will be that much more open to more innovation.

The more formal the approach will, of course, yield better results. It requires touching the most sensitive place: compensation. It also means that a lot of people who are not very well-versed in the startup world (e.g., HR) have to construct an incentive structure that encourages engaging with the startup world. But it is doable, and, when it works, it’s pretty awesome.

Bonus Content:

Capturing Talent: What’s needed for corporate venture fund leaders

A corporate venture capital fund (CVC) is similar, but different from, a traditional venture capital fund. As such, the skill set a managing partner needs to run it effectively is akin but not identical.

Let’s break down the critical and the optional skills that a successful candidate will display.

Critical skills of a CVC managing principal:

  • Marketing – As we discussed in parts three and four of the series, “pilot first with a hard-commit follow-on if it works” is essentially a “pull strategy”. Instead of a “push strategy” of beating the bushes hunting for startups, here you need to climb a hill, unfurl a large flag, and yell at the top of your lungs while waiting for startups to come to corporate. Since this relies on getting the word out far and wide, the marketing moxie to pull this off is essential.
  • Political savvy – Ensuring that line management ultimately does engage with startups requires a mix of politics and process so that the managing partner must create informal relationships to smooth the path to pilot. Not all managers are equally excited about innovation, so finding someone to gently cajole and smooth ruffled feathers is key.
  • Process passion – The managing partner also has to work out a series of touch points and events with corporate. Also, since you get what you measure, he or she will have to help modify the evaluation processes and compensation structures to make sure that working with innovative startups is something that gets his or her partners in management their bonuses and promoted. So, you need someone with some serious operational expertise to sweat these details.

Less critical:

  • Domain expertise – Ideally, you want both venture and industry experience, but that’s a pretty hard combo to find. Fortunately, believe it or not, domain expertise may not actually be all that important. A good generalist investor can get up to speed on a new industry quickly, especially given the deep bench strength of industry knowledge the corporate sponsor brings to the table. So, in a pinch, finding someone for the CVC with experience in the field is less critical than it would be for a standalone fund.
  • Industry relationships – By the same token, the CVC can lean on the cumulative relationship base of the corporate parent. Furthermore, since the primary set of relationships that the CVC needs to forge are internal, between startups and the business lines, not external, extensive industry relationships are also “nice to have” only.
  • Sourcing – With this pilot-to-invest strategy that attracts the startups to the CVC, traditional VC sourcing techniques are less important.
  • Valuation – The lead investor in the startup’s round sets the valuation. Since the CVC is following, the managing partner just needs to accept the valuation set by the lead investor or simply pass on the round. Also, since strategic imperatives often outweigh pure ROI for the corporate parents, it is not the end of the world if a CVC occasionally overpays a little.
  • Deal structuring – Deal structuring also is determined by the lead investor. As long as the CVC gets the same protections as the lead, there is not much to do here.
  • Due diligence – The CVC can free ride on the lead investor’s diligence if it wants, especially since it has already piloted with the startup and has had an extended inside look under the hood.

Where to find this kind of investor? Large corporations interested in starting a CVC are 99.99% likely to use a recruiter to fill this role. But for hyper-specialized roles where clients themselves don’t know what they actually need, a recruiter is only as good as the guidance they get.

For a traditional VC, a good recruiter might look for someone on the rise at another venture fund who also has startup experience in the industry. For a CVC role, finding a VC rising star still makes sense, but rather than looking for additional experience at a very small company, operational experience at a large company and/or top consulting firm is more likely to check the critical skills boxes above.

Acknowledgments: I’d like to thank David CoatsDavid GersterBlake Luse, David TetenLinda Isaacson, Jill Ford, Stacey WallinAmeet Amin, and everyone else who contributed their thoughts to this article.