Confessions of an Anxious VC

Photo by  Rob Curran  on  Unsplash

Photo by Rob Curran on Unsplash

My whole life I have suffered from social anxiety.

It’s something that would surprise a lot of people. I am a social extrovert. I am often the loudest (sometimes obnoxiously so) and most outgoing person in most rooms. I get my energy from interacting with others. And yet those same situations cause me anxiety.

Talk about a catch 22.

I have had social anxiety ever since I was a kid. It used to be bad. Outside of a few best friends, I wasn’t able to spend time in social settings with friends outside of work. The first time I hung out in an unstructured group setting (not a birthday party or a sports practice etc.) was my freshman year of high school.

The weird thing was that it was never the act of being social or the event itself. It was the anticipation of being in a social setting that caused the anxiety ahead of time. Once I got there, I was fine. In fact, I was more than fine. Being social is when I am at my best.

Luckily, I was able to get help. My parents had the resources to pay for me to see a psychologist when I was in middle school. Vocalizing my internal thoughts made a huge difference. Often my own self-talk sounded laughable when said out-loud. By talking about my feelings with an objective third party, I was slowly able to shift the way I talked with myself. I am so grateful I had the opportunity to get help and it breaks my heart that asking for help with mental health still seems to be so stigmatized by our society. I can honestly say that I would not be where I am today without it. Healthy, happy, and (mostly) well-adjusted.

But that doesn’t mean I still don’t get anxious sometimes. Anyone who has dealt with anxiety will understand what I am talking about. The anxiety never really goes away. You just learn to deal with it.

For me, the best strategy was “faking it till I made it”. Every time I threw myself into a social setting I was anxious about, the little voice in my head telling me I wasn’t good enough whispered a little bit more quietly. I acted like I was confident and before long I started to actually feel confident. Over time that little voice went away almost completely.

But it still crops its head up every now and again.

Especially when it comes to networking.

I don’t know what it is, but networking has always given me a spot of trouble. I guess it is just the fact that I generally don’t know anyone at all. True or not, I have this idea in my head that everyone else knows each other and it is easy to get intimidated by that.

Now, you can see why this is a problem.

As a venture capital investor, networking is a big part of my job.

Cultivating a network of relationships with entrepreneurs and other investors is one of the keys to success in this career. It’s not always easy, but I have come up with a few strategies that help me and that may help other people.

Learn someone’s story

The biggest improvement in my ability to network came after re-framing the entire activity. A former colleague of mine was always getting drinks with people after work or meeting up with people in his network for lunch. Most of these connections were people he had met briefly or only a couple of times previously. I had no idea how he did it. When I finally asked him how he was able to network so effectively his response was to tell me that he just liked “hearing people’s story.” As soon as I heard that it was like the clouds parted. I love meeting new people and learning about their story. Ever since I reframed networking as getting to hear people’s stories, instead of focusing on how to present my own, it has gotten exponentially easier and more fun!

An inch wide and a mile deep

Another big key has been focusing on quality over quantity when it came to social connections. I would get overwhelmed by feeling like I would never be able to talk to everyone at an event. So now I don’t even try. I focus on trying to make a smaller amount of deeper connections. I would rather have two 20-minute conversations than eight 5-minute conversations. Aside from just taking the pressure off, I also think this is just a much more effective way to network. If you have a superficial conversation with someone for 5-minutes, you will get lost in the noise. Talk to someone for 20-minutes about the harmonica or the frequency of lightning strikes around the globe and you can be sure that you will stand out.

Go with a friend

When in doubt, guilt-trip a buddy to going with you. Just knowing that you know at least 1 person in a crowd makes a ton of difference. Even if you split up once you get there, it is comforting to know you have a security blanket of someone you already know to talk to in case you need it. And if the event sucks, at least you have someone to laugh about it with.

Nobody cares what you say

This may sound a little depressing at first, but I actually think it is really empowering. The beauty of being in a social setting where you don’t know anyone is just that, nobody knows you. If you say something stupid or put your foot in your mouth, guess what? Chances are that you never have to see those people again if you don’t want to. Maybe you aren’t quite as prolific in putting your foot in your mouth as I am, but the logic even works for boring superficial conversations. Don’t stress about making an impact on every person you talk to. See point number 2 above. If you aren’t jiving someone and you just can’t get them to bite, don’t stress. They won’t remember.

**For the record, I think this tip has a ton of applications outside of networking, especially when it comes to creating content online. People are too afraid of what other people will think about what they say. The truth is, if you say something dumb (like I have many times), no one will care (unless you say something really, really dumb or offensive). On the flip side, make some interesting points and people will take notice. Minimum downside. Maximum upside.

Pick a color, any color

This is a fun one that I picked up from a podcast. If you are anxious about a networking event, pick a color. When you get to the event, talk to everyone there who is wearing that color. It’s that simple. I don’t know why, but for some reason having a mission when you walk into an even (talk to everyone wearing green) really helps. I enjoy this one so much I even went as far as to buy 6-sided dice on Amazon that have different colors on each side. Before any networking event, I roll the die and try to talk to everyone wearing whatever that color is. I don’t know why this one works, but it does. Give it a try.

Go against the grain

I picked this one up from Tim Ferris. When you get to an event, look where everyone is focused. It may be the food table or a celebrity whose attention everyone is trying to get. Ok now see that group focus? Head in the exact opposite direction. It is tough to stand out in a crowd. Give yourself the best possible opportunity you can by going against the grain and doing stuff other people aren’t. This means going to the more esoteric info sessions. It means doing the weirder activities. If you are doing things differently than everyone else, people will take notice. And even better, you will see the other people who are doing the same. Those are the people you want to talk with.

Hopefully this post is as helpful for you to read as it is for me to write. Mental health is hard. Talking about it makes it less so.

As with most things, overcoming anxiety is a slow and painful process.

Each step feels like you aren’t making any progress.

It’s only when you look back that you see how far you’ve come.

Due Diligence: How Much is Too Much?

Venture Capital Technology Startup Due Diligence

A big part of my job is due diligence. This is a fancy bit of jargon that gets thrown around a lot in finance. All it really means is doing research to back up whether things that someone has claimed about their company are true. My boss is fond of reminding us that in our job we need to “trust, but verify.” Due diligence is that verification.

Spend a little bit of time in venture capital and you quickly discover that the rigor of different firms’ due diligence processes vary greatly. Some firms spend an incredible amount of time and resources digging into every small detail of a company. Others run light processes that can be completed quickly. At Rev1, we have what I believe to be a relatively robust process compared to other investors at our stage.

This spectrum makes sense.

Firms with more specific sector-focuses are likely subject matter experts on the spaces they invest, cutting down on time necessary to get themselves up to speed.

Firms that invest across a series of stages will likely have leaner due diligence processes for their earliest investments and more in-depth processes for their later investments. The idea here being that the effort per dollar of investment remains relatively constant. More dollars. More effort.

There is no right answer on what is the perfect amount of due diligence.

But there are wrong answers.

Conducting no due diligence can’t be correct. But doing too much diligence makes your life miserable (and the entrepreneur’s life you are working with even more so).

When I was at Carlyle, one of our founders was fond of saying “you should never focus on conducting the most complete, perfect due diligence. By the time you will have completed it, the investment round will no longer be open and it won’t even matter because you will have talked yourself out of doing the deal anyways.”

I think there is a good amount of truth in this. Venture capital is a risky game. You will never be able to conduct such a thorough due diligence process that you are able to remove ALL the risk from a deal. If you were able to, they wouldn’t exactly be able to call it risk capital investing now would they?

So the correct amount of due diligence lies somewhere between 0 and 100. But where?

I have been thinking about this question a lot recently. The answer (as with most things in business) is that it depends. It depends on the characteristics of your firm and the demands of your stakeholders.

My views on the optimal amount of due diligence have recently been informed by my reading of Fooled By Randomness by Nassim Nicholas Taleb. This is an excellent book which I highly recommend. The author is a veteran options trader and a foremost expert on probability and randomness.

Two concepts from his book have especially informed my views on due diligence.

The first is the idea of satisficing.

Satisficing is a decision making strategy where someone analyzes different alternatives until they find one that reaches a minimum acceptable threshold. And then they stop. I believe this concept should also be applied to investment due diligence.

Your goal should be to reach the minimum required confidence threshold necessary for you to make an investment while expending the least amount of effort and resources necessary to get there. Any additional due diligence past that point is a waste of your, and the entrepreneur’s, time.

This minimum required confidence threshold will change from person to person and firm to firm, but I do think there is value in understanding the idea of satisficing to help avoid using unnecessary time and effort. As with many things in life, due diligence follows the law of diminishing marginal return. Each additional level of comfort you can reach in an investment requires exponentially more and more effort. This is why it is so important to reach your required confidence threshold and to go no further. Even pushing on just a little bit can require a colossal amount of energy.

Not only is too much due diligence a waste of time, money, and energy, but it could actually lead to some pretty large cognitive blind spots.

The second concept from the book that applies to due diligence are the negative side-effects of conducting too thorough of an analysis.

Too thorough of an analysis?

Yes, that is right. Taleb points out that one of the major cognitive biases exhibited by people is that their confidence in the likelihood of a given outcome increases linearly with the amount of effort they expend analyzing the chances of its outcome. It’s the effort people put in to an analysis more so than the analysis itself that tends to influence people’s expectations around an event.

People trick themselves into thinking that more analysis = more certainty, when nothing could be further from the truth. The wrong kind of analysis will be a red herring that increases your confidence in, without actually increasing the accuracy of your predictions.

Venture capital due diligence is an environment ripe for this sort of error. In early stage VC, the risks are so incredibly high for every company. Conducting an excessive amount of due diligence doesn’t change this fact. But it does make us feel better about the investment. This dislocation between the actual risks of an investment and someone’s perceived risks can lead to incorrect decision making and overconfidence in those decisions.

The true danger is not in the risks itself, but in conducting so much analysis that we convince ourselves that the risks no longer apply.

With the ideas of satisficing and the dangers of over-analysis in mind, I believe the best way to conduct due diligence is to seek the no. “Seeking the No” is a cool sounding phrase that I just made up on the spot. The concept is to figure out the few things that would immediately make you say no to an investment and try to validate whether they are true or not. Work backwards from biggest things that would immediately make you cut bait with the company. If you find out any of these hot button issues are true, you can pack up shop right then and there. No more analysis necessary.

Assuming you can attain some comfort that the company does not breach any of your “DO NOT INVEST” red flags, then you can proceed with seeing if they fit what you actually want to see in an investment. What exactly those attributes are that you should be looking for is a topic for another post, but following this strategy of seeking the no should help you focus your efforts on only the investments that truly warrant your time.

Venture capital due diligence is a tale of modern day Sisyphus. You will never be able to truly understand all the risks inherent in a business. Trying to do so wastes precious resources, while giving yourself a false sense of security. Conduct the minimum amount of due diligence necessary to reach either a no or a yes. You will thank yourself for it. And so will your entrepreneurs.

Board to Death

Photo by  Drew Beamer  on  Unsplash

Photo by Drew Beamer on Unsplash

The world of Venture Capital is very different than it appears from the outside. I have been surprised by many things since becoming an investor, but none more so, than the difficulties surrounding boards. From the outside looking in, boards appear simple. Incentives are aligned. Everyone wants what is best for the company. Experience and expertise are leveraged to make the company the best it can be.

If only it were that simple.

Properly managing boards as an entrepreneur is a dance. Defer to them too much and you will lose the magic that made board members want to support you in the first place. Don’t heed them enough and you will make avoidable mistakes and miss out on opportunities.

The biggest mistake I see entrepreneurs make in respect towards their boards is that they think about their boards with the wrong mindset. The second you grow mistrustful of your board and start thinking of them as antagonists trying to put up hurdles in the way of your company, the chances your company is going to become successful with you at the helm plummets to almost zero.

Alright, Erik chill out. Classic Berg exaggeration.

No I am serious. A toxic board relationship is THAT deadly. It may not happen that day. Or that month. But eventually allowing the relationship between you and the board to fester will come back to bite either you or the company. Or both.

I believe the best metaphor for a well run board is to think of the board as your boss. Because that is exactly what they are. The keys to a healthy relationship with a board are the same as with a healthy relationship with your boss.


As with most relationships in life, the most important thing when managing a board is communication. Regularly update your board (even, and especially, outside of official board meetings) on your successes, failures, and any ways that they can help. I maintain that investor updates are one of the highest leverage activities any entrepreneur can do. Keep your board in the loop with what is going on with your company and they will be able to leverage their experience to help you make the best possible decisions. Note that I am not saying to do whatever your board tells you to. If they knew what was best for your business in every possible scenario, they would’ve started your company themselves. Rely on your intuition. It got you this far. But your board has many lifetime’s worth of additional experience than you do. Use it. Take it into account and leverage it to make the best possible decisions. To do otherwise is simply foolish.


Just like all good bosses, boards have a responsibility to develop the CEO. Most startup entrepreneurs have not built a business before. Those that have, in all likelihood, have done so in a different sector or space. The board has a responsibility to coach and mentor the CEO to be the best that they can be. This means giving your CEO the tools they require to be successful. Equip them with resources and connect them with mentors who have been successful in this space before. A board’s fundamental job is to protect the interests of a company and its employees. The best way to do this is by making sure that the CEO performs at their absolute peak. If you as a board member believe your duty is to provide oversight without nourishment, advice without mentorship, you are neglecting your responsibilities to the company.


Communication is a two way street. Yes, the impetus lies squarely at the feet of the entrepreneur, but at the end of the day, they will only feel empowered to bring everything to the attention of the board if the board knows how to give appropriate levels of feedback. Successful boards design structures where they can hold their CEOs accountable in a constructive way. I think Fred Wilson has the best approach for ensuring that feedback loops are tight and honest. Entrepreneurs, don’t get defensive when the board gives you feedback. Every single one of their incentives is aligned with the success of the company. So are yours. Remember that they trying to help you make the company the best that it can possibly be.

From the outside looking in, no one will know how healthy your company is. You can survive with a bad board relationship for a little while. But, if you are consistently neglecting your relationship with your board, eventually it will blow up in your face. The key is to leverage their experience and remember that they are on your side.

Is Venture Capital right for your Business?

Is venture capital right for my business

So you’ve built a business. You’ve got an interesting idea and you think there could be potential for growth. In this post I am going to help you think through whether or not venture capital funding might be right for you and your business.

What is Venture Capital Financing?

Venture Capital is the riskiest of risked capital financing. It is chiefly used to support technology startups. VC firms receive money from investors such as high-net worth individuals, pension programs, and corporations and invest that money into companies in exchange for a portion of the ownership of said company. VCs are compensated with management fees on the amount of money they are managing (usually around 2%) and they also share in the gains on each investment in the form of carried interest (usually 20% of any gains). Carried interest (allegedly) got its name from ship captains who would receive 20% of the cargo for any goods that successfully completed the journey. Carried interest comes into play whenever a gain is realized for an investment. This occurs when A) the company is acquired by another company or B) when the company goes public. That’s it. There are other fringe ways for a investors to get liquidity (fancy word for their money back), but for the most part every investment is taken with an eye towards one of these two scenarios eventually occuring.

I note the incentive structures at play here because it is important to understand one key tenet of Venture Capital:

When the company wins, everyone wins.

Now there is obviously a TON of nuance to this statement and a host of different scenarios that can play out in the chaotic adventure that is investing into startups, but it is important to understand that at the core of any investment, the entrepreneur and the investor’s incentives are, by-in-large, aligned.

Different VC firms invest in different types of companies across a variety of stages. Stages represent how mature a business is. There are three important buckets of stages to remember. Seed stage companies (Pre-seed, Seed, Seed+) are in their infancy and usually have yet to successfully deploy a product at any sort of scale. Early stage companies (Series A, Series B) have successfully launched their product and are starting to ramp up their scaling efforts. Growth stage companies (Series C and later) have an established business and are focused on expansion. After growth you get into the world of more mainstream Private Equity. My focus is on the Seed and Early stages.

Is Venture Capital Funding Right for your Business?

My favorite metaphor for venture capital is from Josh Kopelman at First Round Capital. He says that venture capitalists are like jet fuel salesman. Jet fuel is awesome when you are building a jet. It is significantly less awesome when you are building a motorcycle. There is nothing wrong with building a motorcycle. In fact, motorcycles are pretty sweet. They are just not built to successfully and sustainably use jet fuel. Similarly, Venture Capital funding is not right for every business Here are some of the characteristics that a business needs to have before a VC will consider it for an investment.

First, a business must have the potential for an exit. Remember, for a VC to get their money back to their own investors (and hopefully make some money themselves) there has to be a pathway to that company eventually having an exit to an acquirer or to the public markets. There doesn’t have to be (and usually isn’t) an obvious acquirer, but there has to at least be the potential for an acquisition one day down the road. What about the public markets? Going public through an Initial Public Offering is the holy grail for venture capitalists. Like the holy grail, it is an outcome that is very difficult to find. While this exit strategy is often discussed, it is rarely focused on (or at least should be rarely focused on), especially at the seed and early stages. Having a company IPO is a fantastic outcome for investors, but there are so many things that need to align perfectly for this to occur, that it is rarely worth focusing on too much before the company has some serious momentum behind it.

The second key characteristic is that the company must be scalable. Scalability can take a lot of different shapes, but at the end of the day, there must be significant potential for a company to grow before any venture capitalist will consider it for an investment. Growing the business is what a VC will want their money to go towards. Profits are not the goal in early venture capital. Many startups that could be profitable, choose not to so that they can pump their money into the growth of their business. An initial upfront investment of time, money, and resources can propel a company to significantly greater heights much, much quicker than it would be able to achieve on its own. A company doesn’t need to have its entire growth plan figured out to receive an investment, but it does need to have the potential for growth. A business that is overly reliant on the expertise of the founder will have a difficult time attracting venture capital investments because individual humans don’t scale. Technology scales. Business models can be designed to scale. But people don’t. This simple fact is why the bulk of venture capital investments goes to software companies. Software takes a lot of upfront effort to build, but once it is built, it is relatively easy to duplicate and distribute it.

The final key characteristic is that the company must do or make something of value to someone. This may sound obvious, but I can assure you that, in practice, it is anything but. I have seen startup after startup come along that may be doing something novel or interesting, but it isn’t creating any real value for anyone. The best framework to think about whether your company creates value or not is to consider what problem your company is solving. How many people are experiencing that problem? How acute is the pain they are feeling? Is it a “hair-on-fire” problem, or is your product a “nice-to-have” item? Thinking through these questions will help you pinpoint who your potential customers are and whether they would be willing to pay for your good or service. You can build a successful business if the problem you are solving is experienced by a large number of people or if it is a Top-5 pain in the lives of whoever is experiencing it. The best companies solve problems that are both. Companies solving problems that are neither will not be successful as venture investments.

Is Venture Capital Funding right for YOU?

Even if your business is perfect for venture capital funding, venture capital funding may not be right for you. As an investor, I assume that every investment I enter into is going to be at least a 10 year relationship. When a company takes a venture capital investment, it is a lot like a marriage, and it can be even harder (and more painful) to get out of. If you take an investment from a VC firm, you are ultimately giving up control of your company’s destiny. The where and how are all up for discussion, but at the end of the day, your new investors will eventually require some sort of exit of the business. And they have the power to make this happen. VC’s investments have controls built into them meant to help them safeguard their investment. This may sound severe, but it is important to remember that VCs are, for the most part, managing other people’s money, not their own. They are managing money that comes from college funds, firefighter pensions, and government coffers. VC’s have a responsibility to responsibly manage their investors’ money and they put protections into place to make sure that they can do this. If this lack of control sounds like a deal breaker for you, venture capital funding simply may not be for you. The system works great when all parties have a shared vision for the company. It works considerably less well when a founder has a different vision for their company than their investors. That is why it is so important to know exactly what you are getting into.

Be Honest with Yourself!

Venture Capital is a tool to help companies grow. As with any other tool, applying it in the correct circumstance will determine whether it is effective or not. Be honest with yourself about whether venture capital is right for you and your company. It is not without its downsides, and it is a train that is incredibly hard to get off of once you have hopped onboard. But for the right companies, there is no better way to build a business. Successful companies can be built without venture capital funding, but it is important to remember that these situations are the exceptions that prove the rule. The VAST majority of major technology companies utilized some form of venture capital at some point in their life cycle to accelerate themselves past competition.

There are alternatives. Companies can be built with nothing more than the blood, sweat, and tears (typically lots and lots of tears) of the founder. This is called bootstrapping and can be an excellent strategy for founders that are unwilling to give up control of their business or who do not have ambitions of making their business grow to its optimized potential. Small business that aren’t scalable can utilize small business loans to help them get going. There are even new alternatives for startups like and Clearbanc.

However you decide to fund your business, make the decision with eyes wide open, knowing that there are pros and cons for every option.

Venture capital is an excellent option that you should absolutely consider.

Just make sure you are building a jet before you start pumping in the jet fuel.

Podcast of the Week: The Twenty Minute VC with Fred Destin

Twenty Minute VC

The first podcast I started listening to regularly when I really started to dive headlong into the VC world was The Twenty Minute VC with Harry Stebbings. His bite-sized episodes were a great place to get started in learning more about the ecosystem. Harry’s story was a great inspiration to me as well. His advice to get out there and start creating content was a big part of the reason I decided to get this blog started. Harry has been a huge help to me and is an excellent example of how hard work and determination can really take you places.

I have listened to A LOT of 20VC, but this episode is up there with my favorite ever. Fred Destin is Harry’s partner at Stride.VC. and I can honestly say that this is the first time I have ever finished a podcast and then immediately started it over from the beginning. After listening, you may want to do the same! I can honestly say that Harry has found himself one hell of a partner and I for one could not be more excited to follow their new fund closely!

How often should you update your investors?

Venture capital investor updates from entrepreneurs

Regular investor updates are one of the highest leverage activities entrepreneurs can do to make their company successful. They provide tangible value to companies and a positive signal to investors. And they don’t have to be hard.

If you follow me on twitter, you will have noticed that investor updates have been a topic on my mind a lot recently. There is some debate in the industry about how vital they are and what form they should take. Hopefully this post can codify my thoughts and be a resource to any entrepreneurs.

Help me, Help you

Should investor updates even be done? The answer is an overwhelming YES. Not to be confused with an emphatic YES or a confident YES. An overwhelming YES. Updating your investors is important for a few reasons.

First, investors cannot help you if they don’t know what you need. Investor updates are an opportunity to ask for help/guidance/connections. It may seem intimidating to open your company’s komono to some of the less than glamorous aspects of the business, but by the time investors find out about issues on their own, it will often be too late for them to help. This of course all operates under the assumption that your investors are able and willing to help you. If they are, great! Update them. If they aren’t, why are they your investors in the first place (a topic for another post perhaps)?

I am going to let you in on a little secret. Investors want to be helpful! There are better ways to make money in finance than being a VC. For the most part, VCs have an itch to help build the next great thing and providing help to portfolio companies allows them to scratch this itch. I know that is the case for me. Anyday I can make a fruitful introduction or help clean up a model for a portfolio company is a good day in my book. I think any other good investor would agree.

Brent Beshore describes entrepreneurship as a “daily knife fight”. It is not easy. Founders are faced with new issues and obstacles every day. Mobilizing your investors can help solve a lot of those problems. Why turn down a resource that is not only willing, but excited to help you succeed?

Timing is Everything

As with many things in life, the key to investor updates is consistency. Developing a regular cadence with your updates will take a lot of the punch out of anything that is less than perfect. An email received after not hearing from a founder for 6 months saying that a company missed one of their revenue milestones and need help hiring a VP of engineering seems like a catastrophe. An explanation of why a milestone target was missed and a request for help hiring a VP of engineering received as part of a regular investor update is a Tuesday.

There is some debate in the industry on how often companies should be updating their investors. Some investors believe quarterly updates are sufficient. This may work for later stage companies, but for early stage companies, I believe that monthly investor updates are always the way to go. Monthly updates allow you to keep your updates brief and to the point. In-depth strategic discussions can be left for quarterly board meetings.

How Much is too Much

Entrepreneurs have enough on their hands, so investor updates absolutely must be designed to keep the burden to a minimum. With a monthly cadence, your update can be brief. I suggest that entrepreneurs don’t spend more than 15-30 minutes putting together their update. Items noted should be whatever is top of mind. You don’t need to write a novel, just give your investors a sense of the momentum of the company and make any asks you need help with. Here is a template:

Hello Investors,

XYZ month was a productive one for ABCify! This month we accomplished A, B, and C. We are excited about Initiative X and are thrilled about new hire Y. We continue to execute on plan Z.

Thank you for your continued support,




  • Win 1

  • Win 2

  • Win 3


  • Challenge 1, brief explanation

  • Challenge 2, brief explanation

  • Challenge 3, brief explanation


  • Metric 1

  • Metric 2


  • Ask 1

  • Ask 2

That’s it. Seriously. If you fill in the blank with the above template your investors will LOVE you. This is a good thing. Happy investors make for happy fundraises. More than that, consistent updates are a very positive signal for investors. It shows that the entrepreneur is on top of things and is being thoughtful about their company.

And it shows that the founder is smart.

Because spending 15 minutes keeping your investors happy and leveraging their expertise to help you overcome obstacles is one of the most high-leverage activities you can do as an entrepreneur.

An Introduction to Opportunity Zones

My wife and I are celebrating our 1-year anniversary this weekend with a quick getaway to somewhere yet-to-be-disclosed (I planned and surprised her with our honeymoon and now we plan to switch off for our anniversaries moving forward). As such, this week I will be doing a somewhat abbreviated post. Don’t let the brevity fool you though, the topic of Opportunity Zones is one that I am spending a lot of time researching and thinking about. This piece of legislation passed as part of the 2017 tax reform has some exciting implications for investors and low-income communities In the above video, Steve Glickman co-founder of the Economic Innovation Group (the lobby group that pushed for this legislation) outlines what exactly opportunity zones are at a high level.

(Side note: I read a very interesting article on why some of the measures of growing inequality and lack of financial prospects in this country may be overplayed that you may find interesting. My view is that there are definitely structural problems that need solving, but it requires a more nuanced approach than sometimes suggested. I think Opportunity Zones (OZs for the cool kids) can be that approach. Anyways, back to your normally scheduled running train of thoughts from inside of my head)

My understanding of how Opportunity Zones work on a high level (not tax advice):

  • Investors can defer taxes on existing capital gains by investing those gains into an Opportunity Zone fund for up to 9 years

  •   If those gains are held in the fund for over 10+ years, the investor does not have to pay any taxes on the additional gain those funds have realized over the life of their investment

The purpose of this initiative is to spur economic development in emerging market areas within the US. The incentive is investment type agnostic so venture capital investors can take advantage of these incentives alongside other investors such as real estate and private equity. The IRS just released some very investor friendly initial guidance, but there are still some questions that remain to be answered.

If you want to learn more, below are some excellent resources that I have been using to get up to speed on the potential opportunity (come on you knew I was going to do it at least once. Be impressed I showed this much restraint).

Economic Innovation Group - The lobby group that pushed for the OZ legislation. Their site is a great resource for the latest developments for the program and also has some interesting resources (including an OZ map that is weirdly fun to play around with).

Hypothesis Ventures - A new VC firm that was formed with the sole intention of investing in opportunity zones. Their website is a great resources as well as their podcast and some of the press coverage they have been receiving

Upside - One of my new favorite podcasts highlighting startups outside of Silicon Valley (sound familiar). They have a great episode with the founder of that is definitely worth a listen!

The Big get Bigger: An Analysis of the Current Venture Climate

Figure 1. Via NVCA. As of Q2 2018.

Figure 1. Via NVCA. As of Q2 2018.

Anyone familiar with the venture capital industry will know that we are in an investing and fundraising environment that is relatively unprecedented in the history of venture capital. The rise of “mega-funds” totaling sizes of up to $100 billion in the case of Softbank’s Vision Fund, has lead to deals at sizes that have never been seen before. Uber’s most recent $500m round lead by Toyota valued the company at over $70 billion dollars. The high-dollar amounts and the relatively frothy fundraising environment have instigated headlines ranging in size and shape but almost universally pessimistic as to the outlook of the industry. Some people believe that we are in a bubble the likes of which has not been seen since 2000. Others, especially LPs, Corporate VCs, and Growth Equity shops believe it is an excellent time to get increased exposure to the space. I did some digging into the data to try to find out exactly what is going on.

Here’s what I found.

We are a long way away from seeing Dot-com crash levels

Figure 2. Via NVCA

Figure 2. Via NVCA

Some have compared the current venture climate to the Dot-com bubble of the early 2000s where companies could go public and double their value just by adding “.com” to the end of their name. Everything quickly came tumbling down and investors discovered that simply putting something on the internet was not a way to create lasting value. Despite high-valuation numbers, the current environment remains a far cry from the Dot-com bubble. As Figure 2 illustrates, the current climate is the outcome of an elongated period of sustained industry growth and demonstrates neither the hyper-acceleration of deals we saw in 1999 nor the crash’s sizable peak investment amount. If we are in a bubble, it will look very different when it bursts.

Fund sizes are not as big as you think they are

Figure 3. Via NVCA. As of Q2 2018.

Figure 3. Via NVCA. As of Q2 2018.

This one surprised me and definitely flies in the face of the popular narrative. When looking at the industry as a whole, fund sizes are not meaningfully larger than they were a decade ago. What is important to notice though is how the spread between the average fund size and median fund size has expanded. This indicates that the absolute largest funds at the top of the spectrum are dragging the average fund size up as the median fund size has risen much more modestly.

But median follow-on fund size is increasing…

Figure 4. Via NVCA. As of Q2 2018.

Figure 4. Via NVCA. As of Q2 2018.

…even as the time between funds shrinks

Figure 5. Via NVCA. As of Q2 2018.

Figure 5. Via NVCA. As of Q2 2018.

These trends definitely show the frothy fundraising environment that firms are enjoying. Venture firms have been able to raise larger follow-on funds more and more often. This phenomenon is not unique to venture capital. I saw first hand at my prior job just how much of a desire there was from institutional investors to gain exposure to alternative asset classes. It will be interesting to see if these trends are sustainable as deals take an increasingly long time to exit.

Deals are take an increasingly long time to exit

Figure 6. Via NVCA. As of Q2 2018.

Figure 6. Via NVCA. As of Q2 2018.

Told you so. The time to exit for venture backed companies has slowly crept upwards over the past decade. The exception to this is companies exiting through a public offering where time to IPO has stayed largely flat and is even slightly down versus a peak in 2012. This speed to IPO makes sense in light of the many venture backed companies that have had their shares publicly listed over the past couple of years including StitchFix, Snap, and Shopify (those are just the high profile ones starting with S! Seriously though do you think there is something there…? I’ve decided that I am going to name my future company Soogle.)

Corporate Venture Capital is getting in on the fun

Figure 7. Via NVCA. As of Q2 2018.

Figure 7. Via NVCA. As of Q2 2018.

One of the hot takes on the current environment I have heard a couple of times now is that “the growth of corporate venture programs is a clear sign that we are in a bubble.” This seems pretty difficult to say with any measure of confidence due to the fact that we have been through a grand total of ONE venture capital bubble before, but it is hard to ignore the growing leverage over the space that CVCs are enjoying. I found it very interesting that the percent of deals that have involved corporate venture arms has stayed relatively flat, even as the overall percentage of deal value has increased by approximately 50%. Corporates are putting significantly more capital to work as they take more ownership in bigger rounds.

Deals are bigger than they used to be

Figure 8. Via NVCA. As of Q2 2018.

Figure 8. Via NVCA. As of Q2 2018.

Speaking of bigger rounds. This chart of median deal size does a great job of illustrating the growth of later stage rounds compared to early rounds. As you can see, the driver behind the growth in deal size really is later stage rounds. This makes sense. There has been an explosion of both corporate VCs and Growth Equity shops to go along with larger mega funds. All of these groups have large funds that need to deploy large amounts of capital at once.

Even within Late stage, deal sizes are being driven by the top of the curve

Figure 9. Via NVCA. As of Q2 2018.

Figure 9. Via NVCA. As of Q2 2018.

This one is very interesting. This chart shows dollars invested into late stage rounds by deal size and does a great job of demonstrating that even in the later stages, the biggest deals are taking up a larger and larger portion of the pie.

Valuations are getting more and more expensive

Figure 10. Via NVCA. As of Q2 2018.

Figure 10. Via NVCA. As of Q2 2018.

Figure 10 shows the increasing pre-money valuations that we are seeing today. What is causing this growth in valuation? The relationship between deal size and valuation can be a little bit like the chicken and the egg. Are deals bigger because valuations are higher and firms need to deploy more capital to maintain their targeted ownership? Or are valuations higher because there is a glut of capital and entrepreneurs are getting more capital for less ownership in their company? Given the similar trends in private equity, I tend to believe it is more of the latter. I believe low interest rates have caused large institutional LPs to allocate more capital towards alternative assets in search of yield. Suddenly managers had significantly higher fund sizes and needed to allocate more dollars to each deal. Entrepreneurs (and investors!) don’t want to be over-diluted and this has pushed up valuations as they are able to command higher valuations for the higher deal sizes.

Seed deal size are increasing (even if relatively less than later stage)

Figure 11. Via NVCA. As of Q2 2018.

Figure 11. Via NVCA. As of Q2 2018.

Seed deals are showing a clear trend of getting bigger too. More deals are being done with larger round sizes. Hunter Walk has a great post about how seed is no longer a discrete round, but now more of a phase where companies may need to raise multiple rounds at higher and higher valuations before being ready for an institutional Series A. I suspect this is one of the big drivers for increasing seed sizes (on top of the macro-trends growing round sizes across the industry).

Angels are surprisingly disciplined (or more likely they are being shut out of deals)

Figure 12. Via NVCA. As of Q2 2018.

Figure 12. Via NVCA. As of Q2 2018.

Angel investors are not following the same trends as institutional investors. Figure 12 shows the growing discrepancy between angel and seed median round size. There are a few potential explanations of this. 1) Angels are maintaining price discipline (maybe out of necessity?) where others are not. 2) Friends and family rounds are not growing the same way other rounds are since they are not exposed to the same institutional LPs as funds are (could be). 3) Angels are being squeezed out of more expensive seed deals. My hunch is that it is likely a mix of all of the above, but if I had to put the blame on one thing, it would be angels getting squeezed out of rounds. For better or for worse, Entrepreneurs would generally prefer institutional investors to angel investors, with the abundance of capital being thrown around today, my guess is that angels aren’t getting into deals because there is simply enough interest from institutional investors to close out rounds. This one is very interesting to me because we are still seeing heavy involvement from angel investors in the deals we are executing at Rev1. Maybe we chalk this one up to the coasts?

So what did we learn from my deep dive? Digging into the statistics showed some of what we already knew, but it also revealed some insights I wasn’t expecting. The largest funds are getting bigger, deals are getting bigger, and valuations are getting bigger. Venture Capital firms are raising larger follow on funds at a more rapid clip than ever before. There are; however, some things we found that fly in the face of the popular narrative. Angel investors are not being effected (perhaps unsurprisingly) by some of the same trends effecting the industry at large, fund sizes are not meaningfully larger when you look at the industry as a whole, and the current environment has not yet reached the heights of the Dot-com bubble.

It is dangerous to rely too heavily on historical events as a sign of things to come. As with most things, the truth is somewhere in the middle.