Why I don’t (usually) meet startups in person

The other day, I tweeted.

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“Contrarian perspective here – it’s ok to *not* meet a founder in person before deciding to invest.”

This set off a tweet firestorm — mostly with people telling me in some form or fashion that I was wrong. (Side note: what I love about the VC industry is that people tend to have incredibly strong opinions based on limited or no data 🙂 )

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Image source: Giphy

It’s interesting — at this point, I’ve been investing in early stage startups for almost 5 years.  And, I still have a lot to learn. But I’ve also personally interviewed 1000+ early stage startup teams.

Most of these teams in person.

And after looking at all this data about interviewing, I believe that it actually doesn’t really matter *for me* whether I interview teams in-person or remotely. Let’s dissect this a bit:

First, why should you interview startup teams in person?

1) I think cultural and historical business norms would say that you should always try to meet people in person and try to build rapport in person to win a deal.

While I don’t think anyone has great proof on this, intuitively, I believe this is true. What better way to win a deal than to fly to a founder and just show up and say, “Hey, I want to invest”.

So for investors playing in highly competitive spaces, this makes a ton of sense. E.g. investors going after a hot series B deal. Or for investors chasing after founders who came from Facebook and MIT who are building the next scooter company that utilizes AI.  Building rapport is really important to winning hot deals.

For me, most of my deals are not hot when I invest. Hah. Often these companies go on to be hot later. But since I’m first check into companies when they basically have nothing, usually it’s just me and the founder’s mom who are investing. Writing the check is in itself the rapport-building activity.

2) You can assess founders better in person.

I also believe you can assess founders better when speaking with them in person. You can detect when there is co-founder tension / drama / something weird. You can detect when a founder is stretching the truth. All kinds of stuff.

I know this because I’m a super blunt / direct person. And, I’ve often called out things to founders directly. For example, there have been many teams over the years where I’ve noticed tension in a meeting between the co-founders. I’ve often pulled founders aside afterwards and mentioned my observations as such.  e.g. “Hey, it seems like there’s some weird tension between you — are you having a lot of miscommunication?”  And every single time, founders have broken down and admitted that they’ve been having some problems.  You can definitely detect co-founder issues in an in-person meeting.

So given these huge benefits, why wouldn’t you meet a team in person?  A bunch of reasons…

1) Unconscious biases.

It’s amazing how a team that is great at pitching can really “fool” you. There have been so many meetings I’ve taken over the years where you walk away from the meeting feeling really pumped and believing that the founders are amazing. And you think, “These are great founders!”

And then, I look back at my notes 24 hours later and re-read everything they’ve done or not done in the last few months, and you think, “Oh, this just sounds ok – they’ve only sorta achieved some things.”

Charismatic people can really fool you. Having charisma is a great trait, just in general.  But, it can mask actual execution.

Moreover, charisma is cultural. What we find inspiring in a leader in the US is very different from what other people in other places of the world find inspiring. So, we have unconscious biases around what makes a charismatic leader. Extroverts, for example, in the US have a huge advantage. We generally think of extroverts as highly charismatic people. But extroverts are not actually any better leaders than introverts. There are plenty of examples of successful introverts who manage to inspired large groups of people towards a common goal. So we let our unconscious biases get in the way in assessing things like leadership because of the way our culture is set up.

One of my learnings over the years in venture is that it’s really important – as much as possible – to be objective.  I try to assess what a team has actually achieved. Or what they are actually doing. But very often, meeting people in person detracts from assessing this, because some founders are much better at selling the dream and others are much worse.

There’s a well known top female VC who works at a very well known VC fund, and she was telling me a few years ago that one day her partnership heard 2 pitches. One of the pitches was by a woman who matter-of-factly just talked about numbers and growth and how she could build a big company. Another pitch was by a man who sold the dream and hadn’t done much of anything. After both meetings, the rest of her partnership talked about how they could really relate and build rapport with the male founder who was quite the visionary. This top female VC, however, realized that, although she was more excited about the male founder’s pitch, when she objectively thought about what he had accomplished, she realized it wasn’t much.  And that the female founder had knocked it out of the park although her storytelling wasn’t as amazing.  This story is a true story and this happens all the time in venture.

In the venture community today, we reward “visionaries” much more than executors. And a big reason for this is that we make investment decisions based on pitches rather than on execution (aka working) in our decision-making.  This is a big problem and this is precisely what I want to change at Hustle Fund (though it takes baby steps).

The last piece about unconscious biases is that sometimes what we see in-person scares away traditional VCs.  Such as pregnant women. Being a pregnant woman and pitching investors is NOT a recipe for success to raise money.  Although there are plenty of successful female CEOs who have children while running their respective startups, it’s still not a positive sign to most VCs.  This is a shame and something that is only noticeable / an issue when pitching in person.

2) Meeting teams in person limits your deal flow.

At the earliest stages, it’s important to see a lot of dealflow.  If you are only doing meetings in person, it means that:

  • Companies can only be located in your geography
  • You need to spend a lot of money and time to fly to other places to see companies
  • You need to spend a lot of money to fly companies to see you.

If you’re a series B firm, all 3 of these can be fine limitations. You presumably have enough management fees to spend money on travel, and presumably, you don’t need to be seeing tons of companies in order to do great deals. But if you are at the earliest stages — such as a pre-seed fund like ours — you need to be seeing lots of deals and generally don’t have the budget to either do a lot of traveling or to fly companies to you.

And at the pre-seed level seeing lots of top-of-funnel deals is critical!

So, meeting teams in person is a tough strategy for small firms like ours — for both time / money reasons.

3) Technology is good-enough for remote meetings these days.

Technology is actually quite good these days. I think 10 years ago, vetting people through video conference might have been rough. But, today, Zoom.us, for example, is an amazing product for doing video interviews. You can see a lot with strong connectivity — including founder tension — and you can really feel like you’re in the room with the founder.

4) Meeting people in person is inefficient.

I don’t want to waste founders’ time and my time. The priority activity for them is in running their business. So for the most part, driving all around the Bay Area (in traffic!) is not a value-add activity for anyone. If we happen to be in the same place at the same time, that’s great — such as a conference / event / co-working space, but for the most part, commutes are a bear that I don’t think anyone should have to put up with if given the choice.

5) Lastly and most importantly, if you construct your portfolio in a certain way, it’s actually ok to miss things in a virtual interview.

At the end of the day, doing VC right is actually much more about portfolio construction and modeling than picking. This is surprising to many people.

After investing in hundreds of startups, I genuinely believe that it is much better to invest based on execution rather than to try to assess accurately based on talking.  But, the entire industry is largely based on making investment decisions based on talking. This is a grave mistake, in my opinion.

Here’s an analogy in the job market — in the old days, you would interview a bunch of candidates. And then you would pick someone to hire largely based on talking. But as it would turn out — people who are great at selling themselves in the interview process are not necessarily the best performing hires! Business people have figured this out, and so these days, at so many companies, you no longer just talk in a job interview. Hiring teams now try to assess in other ways — through projects / short term contracts / tests / etc. In other words, execution-based tests are now used much more commonly to better assess hires.

In VC, the right analogy would be — why don’t we make a small bet for seemingly promising companies? And then try to assess based on execution whether or not to write a much larger check.  (On the flip side, startups can assess us/me, to see if I’m living up to standards as an investor.) And as performers perform, let’s continue to do this. This seems like the much better way to assess performance — by actually assessing performance itself rather than talking.

For this reason, this is why I think it’s actually ok to miss some things in interviewing founders for a potential investment — because I care much more about how a team performs than how they talk & look.

How to build a big marketplace

I’m not very good at keeping up with The Twitters, so I hopped into this conversation about building large marketplaces super late.

It’s an interesting one — when building a marketplace, which comes first?  The chicken or the egg — supply or demand?

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Image credit: Rushart’s blog

Obviously both are important for a successful marketplace!  But, if you want to build a really BIG marketplace, here are some observations from over the years.

1) Unlocking large amounts of supply matters A LOT!

This is a bit unintuitive.  Most people who set out to build a marketplace think that if you can get people to pay for something (the demand side), then you’re all set.  I’ll argue that it’s certainly important to test the demand side but it’s almost more important to test how hard it is to get supply.

From my experience in growing an ad network, it is possible to have lots of demand but not enough supply!  This is actually a very common phenomenon.  Case in point, most email newsletter companies have an easy time selling out their ad slots, but it’s incredibly hard to continue growing an email newsletter at a fast clip.  The way that a lot of email newsletter companies solve for this problem is by introducing new lists with the same audience.  E.g. you can receive the daily news digest and also the daily jobs email.  This gives them twice as much supply with the same audience.

2) If you are aggregating supply, the key is to unlock new supply

One of the big areas where I see marketplaces fail is by going after an existing market and trying to amass the same supply that already exists.  So for example, a marketplace for salons or a marketplace for wedding venues or a marketplace for co-working spaces.  These marketplaces are all amassing existing salons or existing wedding venues or existing co-working spaces.  These are existing places that consumers could ordinarily find themselves and pay for directly.  You are literally just moving supply around and not growing it.  The issue with doing this is that this existing supply already has certain expectations for payment, because they are already making money for this service or asset that they provide.  This then makes it hard to be a middle(wo)man and take a cut in between.  You are competing with a strong alternative — to be found directly.

The better way to aggregate supply is unlock new unique supply.  Airbnb is a great example of this.  People were not already using their extra bedroom as a hotel room or their couch as a bed.  They don’t have the same expectations around making a ton of money unlike the Holiday Inn.  Airbnb has effectively brought a ton of new “hotel room supply” to the market that didn’t exist before.  They were not try to resell existing rooms in existing hotels.  Uber and Lyft are equally good examples of doing this in the taxi market.  They brought into the taxi market new “cab supply” that didn’t exist before, and these drivers don’t have the same expectations for monetization as existing taxi drivers.

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Image credit: Giphy

Ultimately, unlocking new supply drives demand.  If I can stay on someone’s couch next to the Moscone to attend a conference for 50% of what I’d pay for a room at the Holiday Inn, I’d do it.  You are reducing prices for the end user by unlocking new supply, and this drives demand.

So going back to the original examples of marketplaces for salons or wedding venues, etc, can you get clever / creative in creating new supply?  Can you turn new people who are not in the salon business into a salon owner?  In many cases, doing this might just be too high of a cost and not possible, but in some cases, this approach may be a good strategy.  A good example of this is Wonderschool.  Wonderschool is turning people into new daycare owners — they are not amassing a network of existing daycares but rather unlocking and creating new ones to add to their network.  So think about unlocking new supply rather than moving existing supply around.

3) The unit economics need to work in the long run at scale

Once you initially test both supply and demand, there’s going to be a constant tension between both sides.  Sometimes you’ll be supply constrained.  Sometimes demand constrained.  Often, it may not be clear if the unit economics will work out while you’re building this up.

In fact, ridesharing companies often get a lot of flack from the public, because they are not profitable yet.  But, the holy grail for them is autonomous cars.  Once these become mainstream, they will have access to infinite supply at a low cost.  So while the short-term numbers may be questionable, the long-term future of these companies seems very promising.

Similarly, you’ll need to think about what your long term control over supply will be.  Most marketplaces that are successful have a stronghold on at least a good portion of their supply to help with pricing pressures.  Successful ad networks are a great example of this — Google may run a large ad network across many properties they don’t own, but they also own a lot of their own properties including Google search and YouTube.  Likewise, although Airbnb doesn’t own properties today, it’s rumored they are going into real estate.  So once you get some footing on your marketplace, the next question is how can you think about controlling your future by having access to or creating at least a good portion of your supply?

4) What should I look for in amassing unique supply? 

If I were to build a large marketplace today by amassing supply, I would start by looking around at what is currently wasted (space / time / assets).  Then, I’d think about how this wasted stuff might be cleverly transformed into something else that consumers and businesses currently spend a lot of money for.

Summarizing all of this, to make a marketplace fly, you need to cleverly come up with a LOT of unique supply (obv there has to be demand).  1) Turn something else into supply where people don’t have high monetization expectations (Airbnb, Uber, Lyft).  And/or 2) eventually you own it or part of it (e.g. scooters / Google search).

An analysis of going from $0 to $1m revenue in 1 month

At Hustle Fund, we talk a lot about speed of execution. Part of this is grit and founder hustle. But what most people don’t realize is that speed is also baked into the business model itself.

For example, one of the things that people don’t realize is how much sales cycles and payback periods matter.  As a concrete example, fast growth direct-to-consumer companies are now able to go from $0 to $1m revenue within a month or two with just < $25k in ad spend. This is incredibly fast — unprecedented and very low cost.

How is this possible? All because of fast sales cycles. Let’s dive in:

Let’s start with a simple example. Suppose the following:

  • We start with $25k in ad spend on day 1
  • As soon as people click on our ad, they buy immediately and we get that revenue immediately
  • For every $1 we spend on our ads, we make an average $1.15 in revenue
  • We pour everything back into ads the next day
  • You can see that within a month, we are at an almost $2m revenue generated with just initial ad spend of $25k! This is crazy. You can raise a small pre-seed tranche and get to Series B benchmarks within a month.

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Now, in practice, the scenario I’ve outlined is near impossible. Namely, most of the time, your ad spend is not this effective on day 1 and often requires iterations and testing. Moreover, it often takes some time to clear with your payments provider even if you generate revenue right after someone clicks your ad.

But this scenario is actually not that far off from what many of the direct-to-consumer incubators are achieving.

Ok, let’s add some delay to make this a bit more realistic. Let’s suppose:

  • We start with $25k in ad spend on day 1
  • As soon as people click on our ad, we do get our initial ad spend back immediately but we don’t make any profit until the even numbered days
  • For every $1 we spend on our ads, we average $1.15 in revenue (on the even days)
  • We pour everything back into ads each day

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This is a contrived example (profit only on even numbered days??  weird.), but you can see in this example, we went from a near $2m revenue generated at the end of the month to just a $200k revenue generated, even though the delay in our profit is not that long. Not only that, we are making about half the profit as before, but our revenue generated has now dropped by nearly 10x. Why? Because time is a compounding factor.

So when investors are concerned about sales cycles and payback times, this is what they mean. Regardless of whether you are using ads to get customers, if you calculate this out, you can see how just small affects in sales cycles / payback periods hurt you big time. The other thing is that as an entrepreneur, you’re working just as hard in the first scenario as in this one, but your sales are affected 10x.

Both of these examples are still a bit contrived, because as I mentioned above, you usually don’t know if your ads — or any of your customer acquisition channels – are working (they probably aren’t) on day 1.

So now let’s assume that you don’t start with $25k in ad spend.  Let’s start with $5k. Suppose the following:

  • We start with $5k in ad spend
  • As soon as people click on our ad, they buy immediately and we get that revenue immediately
  • For every $1 we spend on our ads, we make $1.15 in revenue
  • We pour everything back into ads the next day
  • We add an additional $5k in ad spend every 5th day

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You can see that with this example, we can get to near $1m revenue generated by the end of the month ($800k+). In this case, we end up spending a bit more on ads, but this is a more gradual (and realistic) approach to ramping up ad spend. Again, in this example, because we make the $1.15 for every $1 immediately, you can see that this helps us achieve greater revenue than in the prior example.

Here is the spreadsheet with these 3 examples that you can copy and play with.  I’d encourage you to fiddle with the levers of this model in the green boxes. The amount you make for every dollar of spend. The payback periods. Ramping up ad spend. Etc.

In your own business, how can you decrease your sales cycle + payback period by even just 10%? How can you increase your margins by even just 5%? These all add up significantly as you can see over short periods of time.

The tl;dr is never underestimate the value of time in making money.

Featured image credit: Freeimages.com

Learnings from a 6x angel investment portfolio

I debated writing this. Partly because I didn’t want to jinx my portfolio. Partly because my gains are all on paper anyway. And partly because when I did my angel investing, it was at the beginning of my investing career when I really didn’t know what I was doing. Hah.

Nonetheless, I do think I’ve had some great learnings that are worth sharing with entrepreneurs and would be angel investors.

1) You don’t need to invest a lot of money to become an angel investor.

I think a lot of people think of angel investors as super rich, investing $25k-$100k at a time. This is what I thought too when I was an entrepreneur. I thought, “Someday, when I get to be super rich, I’ll start angel investing.”

Later I learned that actually a TON of entrepreneurs in Silicon Valley angel invest. And they are not even that rich. How is this possible? I would later meet a number of entrepreneurs who invest $1k-$5k checks into startups.

That was a mind blowing discovery.  You don’t need to be filthy rich to angel invest.  Just like how there are now microfunds. There are microangels.

2) Being an angel investor helps you network

The second learning was that entrepreneurs who are angel investors can mingle and network with fellow angel investors. This allows you to build friendships and rapport with other investors who have more money than you and guess what…they can invest in your company and introduce you to other investors!

This is a great strategy for raising money that I wish I had known when I was building my company.

3) Your small check size doesn’t matter if you are value-add.

You might wonder why any entrepreneur would even accept such a small check of $1k. If you can be value-add, then that really helps you win deals. Because more than money, people want help. Especially at the earliest stages. Think about it — money buys help, so if you can provide help for free, then that’s huge.

Do you know something about engineering? Marketing? Sales? Design? Do you have a good network? Can you provide good feedback on things like marketing materials / landing pages / pitch decks? These are all value-added activities at the earliest stages that help you win deals when you are writing small checks.

4) Your reputation matters most.

A lot of new investors inadvertently are a pain to work with. I hear stories of people who take 5 meetings for just a $25k investment. Or stories of investors who require tons of due diligence for a $10k check, including 5 year spreadsheet projections and extensive business plans.

If you’re new to the game, set expectations for what your process will be like. Be transparent. How many meetings do you typically need to make a decision? Do you want to mentor the company first before deciding? Whatever it is, be transparent with your process so that the founder can decide whether or not he/she wants to go through with your process.

Reputation matters and word gets around very quickly. This will set you up for future deals.

5) Work with founders lightly to learn

Like everything else, investing requires practice. And the only way to practice is if you have a feedback loop. You need to work with your founders after investing in order to better understand what type of company you picked and understand what’s going on in the business / with the founders.

Make sure you are not a nuisance. See above. You don’t need to work with the founder forever. It could be a few meetings to help them with their deck. Or it could be a few meetings to help them with their website. Or UX of their product. Or product testing. But you need to interact with the founder so that you can get better at picking companies.

An alternative to becoming an angel or microangel is to work at an accelerator or incubator.  Or even mentor as a volunteer for an accelerator or incubator.  You will learn a lot about teams and different kinds of businesses.  Accelerator programs see a TON of deal flow and invest in a lot of founders, and you will learn a LOT about investing without risking your own money very quickly.

6) Build a large diverse portfolio

VCs often debate whether you should have a “spray-and-pray” portfolio vs a “concentrated portfolio”. Having built both kinds of portfolios before, I think building a “spray-and-pray” portfolio is the easier strategy to start with.

What do these terms mean?

“Concentrated portfolios” — these are portfolios that have a few number of companies — say 10-20 in total. So if you are allocating say $100k in total to angel investing, you might put $10k into 10 companies. Most Sandhill VC funds are in this camp.

“Spray-and-pray portfolios” — these are portfolios that have a lot of companies in them — certainly 20+ and some cases 100+ companies. So if you are allocating say a total of $100k to angel investing, using this strategy, you might put $1k into 100 companies. YCombinator and 500 Startups are examples of this approach.

A lot of investors have strong opinions about which is the better approach. Having looked at the data, you’ll see big winners and losers utilizing each strategy.  So, like everything else, it’s really a matter of how good and lucky *you* are.

I think the spray-and-pray portfolio strategy is easier to start with, because there’s room for a lot of error.  Your initial investments will likely be horrible, because you won’t know what you’re doing.  This method gives you a lot of shots at trying to capture a super huge winner, much like how YC has Airbnb and Dropbox.

Statistically speaking, if your sample size of deal flow is “generally good” and you are an “ok picker”, you can at least get to at least breakeven with the spray-and-pray strategy.  A former colleague of mine Matt Lerner, simulates this nicely in a post on the spray-and-pray strategy.

The tl;dr is that in essence, if you have a portfolio of roughly 100 companies, you should be able to pick at least one company that is 100x+ return or higher to get your portfolio to breakeven.  For each additional startup that is 100x+ return, your overall portfolio will yield an additional multiple.  E.g. if you have 3 100x+ returning companies, you’ll have roughly a 3x portfolio multiple.

The question about this strategy that I often hear is whether it is possible to generate say a 50x returning spray-and-pray portfolio?  And the answer is yes – YC is a good example of that.  To achieve this, you must have at least one deca-unicorn (like Airbnb or Dropbox) in your portfolio.

So if you go with the spray-and-pray strategy, you can start to build this over a few years — invest in say 5-10 companies per year to end up with 50-100 companies in your portfolio.  Each year, as you get learnings, hopefully your dealflow and picking gets better.

7) Be patient and don’t freak out.

You will want to freak out in the beginning, because you will see a lot of seemingly losses. This makes sense because the companies that can’t make it will die earlier than later, and the big winners that will return your portfolio won’t get to maturation until years later. So you need to have some faith and a strong stomach. You won’t see your portfolio start to inflect for years!

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Image credit: Tumblr

I was a microangel from 2014-2017 (I no longer angel invest because I now run Hustle Fund).  I invested in 7 companies over those 3 years with $5k checks in 5 of them and $10k checks in 2 of them.  3 of these companies shut down more or less before I had paper gains on the others.  So it was incredibly nerve wracking, because I felt like I was losing all my money!

8) Be prepared to lose all your money!

All of this said, you can always lose all your money. So, be prepared to do so. Angel investing is risky, and most angel investors (and VCs!) do not see positive returns. Don’t part with more than you can handle.

And this brings me to my next point.

9) Investing is all about power law — don’t worry about your losses.

In talking with a number of fund managers and seeing data from my own experience, you can basically think about your portfolio companies in 4 buckets.

1) Non-returners
2) Low returners
3) Good returners
4) Excellent returners

Most of your companies will fall into category #1. And that seems scary. But, as you can see from my portfolio, your losses don’t really matter. In fact, if you copy this sheet and play with the numbers, you’ll see that your low returners don’t matter either! Everything is really riding on your excellent returners, which you won’t have many of.

A few takeaways from this spreadsheet of my angel investments (and please do copy this and play with the numbers):

A) You need at least one excellent returner. I often hear angels talking about looking for 10x returns or 2x returns from their companies. As you can see, you need to be shooting for much much higher in your ultimate winners.

B) Your good returners don’t have as much impact as one might think unless you have a whole handful of them.

C) New angel investors worry about the losses and sometimes get nasty with founders who lose their money.  But in practice, those losses don’t matter either.  If you get nothing back vs $0.20 on the dollar, it’s a wash — it’s literally all the same.

Of course, it’s always nice to receive money back from a company that is winding down. I see that as a good signal about the founder — that he/she is looking out for your interests and wants to do right by you. But as you can see, from an ROI perspective, that dollar amount itself in that category really doesn’t matter.

In contrast, seasoned investors don’t care about the losses and concentrate on the potential winners. You need to try to find as many of those 100x+ returning companies as you can — that is what the game is about.  This is something to keep in mind as an entrepreneur — how can you convince someone that you are a 100x+ winner?

D) You won’t know who in your portfolio is the excellent returner(s) when you start investing. And you won’t know for years.

My portfolio is 3-5 years into angel investing, and all of this is paper gains.  So all fake gains right now.  Any one of these companies could go belly up at any time.  The hope is that one of these companies can inch up to 100x real gains. But we’ll see.

10) Start by co-investing with people who have good deal flow

In the beginning, you won’t have a brand or deal flow. The easiest way to jumpstart your angel investing is to find people who do. Find friends who already have been investing for years and have been doing well. You can also invest in funds, who may share their deal flow and pro-rata rights. Or you can mentor at accelerators or co-working spaces.

Once you start generating deal flow, by continuing to invest, you build up a brand over time.

You will want to see a lot of deals in order to start to compare companies to each other. Seeing a company in isolation won’t help you understand if it’s a “good company”.

You need to understand whether the team is in a competitive market — e.g. are you seeing 10 companies chasing the same thing?  Do you place a bet after seeing a lot of companies or do you shy away from the space altogether?

You won’t know if a company’s revenue growth is good or not until you see other companies and their growth.  The other benefit to being an angel-entrepreneur is that you get to see what is “market” as far as competitive spaces go and growth rates go.  You don’t normally get to see that as an entrepreneur.  That helps you understand how your startup stack ranks.

11) Entry and exit points matter

One of my most surprising learnings from investing the last few years is how much entry and exit points matter. I learned that there are a lot of investors that brag about investing in marquee companies that have done phenomenally well and yet have made little to no money because they got into a deal at too high of a valuation and got out at a valuation that isn’t high enough to cover their other portfolio loses and make money.

Unfortunately, as an angel, you have no control over the exit point. You are just along for the startup ride. So you can only control the entry point.

So for example, if you are shooting for 100x+ multiples in your winner(s), then if you are investing at $3m cap on a SAFE, then roughly speaking, you are trying to exit around the $300m valuation mark (or higher!).  If you are investing in another company at $6m cap on a SAFE, you need that company to deliver 2x the exit of the first company, which is incredibly hard.  Note: historically, the number of new companies that get to the $1B valuation mark each year was less than two handfuls WORLDWIDE, though in the last couple of years, hundreds have been promoted to unicorn status in the startup bubble.

So maybe your strategy is to invest at a low valuation.  Maybe it’s to invest in high valuation companies run by high profile founders.  But whatever your strategy, entry and exit points matter.

12) It’s all luck. No one can spot a winner at the earliest stages.

One final thought — angel investing at the earliest stages is pretty much luck.  Anyone who tells you it’s skill is sh*tting you. You can have amazing founders do amazing things and then get run over by a bus or have some regulation come in and break up the party. And if you’re riding on just your one winner covering your loses and delivering big gains for your whole portfolio, that’s a lot riding on one company. Maybe you have a couple or a few of these winners, but if one falters, then that reduces your multiple by a point or so on a portfolio of 100 companies.

So your best investment is probably to buy a magic 8 ball.

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Image credit: Gfycat

To recap:
-Risk capital you can afford to lose
-Learn from your investing and improve your thought process and strategy
-Microangels are en vogue and being one helps you access other angels
-Structure your portfolio to diversify enough to increase your odds of capturing at least one big winner (at least 50 companies if not more to get a winner of 100x)
-Keep entry and exit points in mind

Featured image credit: CBS News

5 startup opportunities that will be big in 2019

Happy new year!. Lunar new year!  (a month has gone by while I’ve been sitting on this post)

Here are some other 2019 VC predictions that I’ve enjoyed reading:

Here are some things that I think will be big in 2019:

1) Furthering vocational education

I think traditionally, a lot of investors have been shy to invest in education. In US, let’s be honest — we don’t really care about education! Here’s a good post that my friend Avichal Garg wrote on the education landscape several years ago which I think still applies today in the US.

But the tide is changing a bit. Specifically, what we’re seeing in the US is massive student debt. And new college graduates are not able to get a job or a high paying job. For so many people in the US, if you are not majoring in a STEM subject, it probably does not make sense anymore to go to college. Period. The economics of college are just terrible.

So while we don’t care about education in the US, we do care about business and return on investment! And it does make sense now to provide education of “useful” topics for the workplace — for a job, for livelihood. This is why we see the rise of Lambda School which ties your livelihood outcomes to your cost of education.  And there are many other schools that are cropping up such as Make School and Kenzie Academy (we are investors at Hustle Fund) that are trying to teach useful topics that you can actually use and are willing to pay for, because you can use those skills to make money.

I think we will see a lot of new businesses stemming off of this trend.

We’ll certainly see more schools — both in-person and online covering more topics. Everything from coding to digital marketing to sales to even entrepreneurship. But also vocational categories as well. Can you teach medical skills or plumbing skills using VR headsets remotely?

Additionally, I think there will be businesses stemming off of these. Lots of new ways to loan money to students. New ways to provide socialization and networking for remote students. New real estate opportunities for these students.

2) Improving commutes

Commutes are terrible! (and a big waste of time). This year, we will see a lot of businesses built around making your commute better. Commutes can get better in two ways: A) By actually reducing your door-to-door time and B) by making the experience while commuting better. We’ll see opportunities in both.

A) There will be new ways of commuting in less time.

This is really what the rise of Bird and Lime is all about. When it’s faster and cheaper to go from say SOMA to the Financial District of San Francisco by scooter vs car AND is accessible to everyone, people will do it. In contrast, not everyone can ride a bicycle or a skateboard (e.g. more expensive, need balance or skills – not accessible to all)

But scooters really only work in warm-ish places where there are bike lanes / wide enough roads. E.g. places where it snows / places that don’t have bike lanes won’t be great markets in the long run. So there’s an opportunity to come up with a mode of transportation and model that can withstand weather / lack of bike lanes. My guess is that we will just see further advancement of ridesharing combined with autonomous vehicles. An early version of this might be effectively new autonomous bus lines that just go up and down streets continuously.  This is already starting to happen in some cities.

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Photo credit: Giphy

B) As people drive less, they will have more time during their commute

This is a big opportunity for people to do more work, shop, and play more too. For example, we’ll likely continue to see growth in podcasts and tools for podcasts this year. Spotify made clear that they believe in this opportunity by announcing two acquisitions in podcasting this week.

But we might also see the emergence of new commuting activities. Such as new commerce models. In Asia, for example, lots of people shop while waiting for public transportation like this:

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Photo credit: Tech In Asia

Perhaps we will see shopping happen in rideshares — this is already happening — some startups are going after this opportunity.

We may even see new fitness activities. Peloton allows you to exercise at home in a social way. Can you do this on the road? Can you take a stretch class in an Uber? Can you run from Zombies or have a coach yelling in your ear while you run to work?

A general trend we’ve been seeing over the years is the ability to entertain yourself in a retail location, and later this entertainment was brought into the home and then later yet, taken anywhere, especially while commuting.  For example:

Before, you shopped at the mall -> Later you shopped on your Desktop browser at home -> Now shop on your mobile device while commuting

Before, you played video games at the mall -> Played video games on your Desktop -> Now play video games on your phone while commuting

Before, you watched shows at the theater -> Watched shows at home -> Now, you watch shows on your phone while commuting

Before, you went to the gym to workout -> Now, you work out at home -> Later, will you work out while commuting?

Maybe.  I can’t predict the future, but I can tell you that people will have more time with their commutes.

3) Furthering entrepreneurship

When I grew up in the Silicon Valley in the 1990s, entrepreneurship was a ridiculous idea. You were a maverick if you were an entrepreneur. This is no longer the case. You’re pretty mainstream if you’re an entrepreneur today. Even outside of Silicon Valley, so many people have side businesses.

I think entrepreneurship as a category has gotten so big that it needs to be segmented. There are fast growth tech startups — these are the ones that VCs like to find and back. There are brick and mortar retail businesses. Like cafes and restaurants. And there’s a new emerging but fast growing category that I call the “micropreneur”. Micropreneurs are < 10 person companies that are supported largely by existing web platforms and online distribution. With just a handful of people, these founders can generate as much as $100k-$1m per employee because they can leverage a lot of existing infrastructure — online payments, website builders or online store platforms, and even easy-to-use “pseudo-developer tools” such as Zapier. Micropreneurs are fueled by the rise in platforms that help people get a business off the ground — such as Shopify or Webflow (we are investors at Hustle Fund) or Stripe or Udemy. Or even YouTube and Instagram! They are often bootstrapped and often start as side businesses that sometimes become full-time businesses. And unlike tech unicorns, there are tons and tons of them.

I think 2019 is the year where we see products, platforms, and content for the micropreneur.

  • Entrepreneurship education platforms (could be schools / bootcamps / etc of sorts) especially in areas of customer acquisition
  • Loans / financial solutions to provide non-VC funding for these businesses
  • Unique platforms and tools that can make it easy to start a “scalable” micro business
  • networking platforms and clubs (like a YPO for this segment)

In general, I believe that if you can help people make more money, that is the easiest sale, and microentrepreneurs are hungry to buy things that will fuel their businesses that are already doing well.

4) Crypto tools and crypto platforms

Although we’re in the bear markets with crypto, I am bullish on the long term use of cryptocurrency. Why? Fiat works fine in many places.  But, I think what we are increasingly seeing is monopolistic behavior on the internet.

I applaud CEO of CloudFlare Matthew Prince for writing this post a couple of years ago about free speech on the internet.  In this post, he talks about how CloudFlare came to the conclusion they should terminate The Daily Stormer as a client.  It was a difficult decision, not because he agreed with the Daily Stormer’s ideology, but rather because he didn’t believe that internet companies should be policing the internet for people who hold opposing ideologies.

But this is happening.  We’ve seen a lot of large internet companies terminate relationships with people they don’t agree with.  As a response to that, I believe we’ll see new sites crop up to try to bring back a “free internet”.  Payments are usually at the front of new waves of trends, so I suspect, we’ll see decentralized payment options pop up as a response to PayPal / Stripe / et al kicking people off their services.  Technology tends to start off with illicit use cases (such as the VHS tape used for pornography) but then ends up becoming mainstream.

In order for people to pay each other with cryptocurrency, we need reliable and easy-to-use infrastructure that mainstream consumers can use. This includes digital wallets for storing cryptocurrency, easy-to-use exchanges for moving money from currencies to fiat, accounting solutions for cryptocurrency, etc.  Entrepreneurs are currently building in all of these areas, and I’m bullish on innovation in all of these.

In this space – I think the winners will have to be incredible product designers who can build great user experiences.
5) Verticalization of B2B SaaS

In North America, B2B horizontal SaaS business ideas are largely saturated. Not 100%, of course, but for the most part, we have marketing software, sales software, HR software, customer service software, and communications software that largely works. Some of these tools may be clunky archaic experiences, but they are here to stay — at least for a while, in my opinion.

So I think the B2B SaaS opportunities that people will focus on are verticalized use cases.  E.g. Marketo for XYZ industry. Software built around particular sales cycles and workflows for industries like real estate, construction, farming, retail, etc. We already see this happening, but I think there will be a lot more of these types of businesses built around verticals in 2019.

I could be completely wrong on any and all of these predictions! And, even if I’m right, outside of these 5 categories, there will be, of course, many more businesses built.

What startup opportunities do you think will be big in 2019?

Featured Photo credit: World Economic Forum

How I raised my $11.5m VC fund

A couple months ago, we announced that we finished fundraising for fund 1 of Hustle Fund.  Hustle Fund is my new venture capital firm, and our fund 1 is an $11.5M fund dedicated to investing in pre-seed software startups.  Eric, Shiyan, and I could not be more grateful to our investors for their support and to so many of our friends and family who helped us with this process!

I’ve written before about what it’s like to start a new venture capital fund.  But, a lot of people have asked me about how we actually raised it.  Surprise surprise – we ran our fundraising process using all the fundraising tips I give away on this blog!

First some context

I need to spend a minute explaining a bit about venture capital (VC) structures.  VCs raise money from other investors called limited partners (LPs).  These investors can be individuals / family offices / corporations / institutional funds that invest in VC funds.

Here’s how we raised our fund (and some learnings):

1) We talked with a dozen fund managers before starting 

If you are considering raising a VC fund, I would highly recommend talking with a TON of new fund managers before jumping in to a) make sure this is what you want to do and b) get tips and advice.  The single-biggest tip that I heard over and over from my peers was that they felt that they had spent a lot of time courting large institutional fund investors when they should have spent more time trying to find family offices and individuals and corporates to pitch.  We took this advice to heart and ended up only meeting about 10 institutional investors once or twice to build relationships with them – potentially for down the road.

In the startup-fundraise world, this is analogous to raising from angels vs. VCs.  If you’re super early, meeting with angels is likely going to be the more successful fundraising path.  VCs will take meetings with you, but you want to make sure you are not spending too much time with people who will most likely not be investing right now.  That being said, it can be good to build relationships for down the road.  This is a time tradeoff that every founder — both product founders and new fund managers — have to make.

2) We sized up motivations

This leads me to my next point.  It’s important to size up an investor’s motivations – and this applies when fundraising for a product startup as well.  When you’re meeting with an investor, try to understand why he/she is investing — just in general.

There are many many reasons why someone wants to invest money in companies:

  • To make money
  • To not lose money
  • To take large risk but potentially very high return
  • To get promoted / move up the professional ladder by making a good investment
  • For fame and glory and bragging rights
  • To learn about a business or industry
  • To network with other investors or the founding team
  • etc..

Points #1-4 seem similar but they are actually quite different.  Some people are motivated by making money.  Others are motivated by wealth preservation (to not lose money).  An example of this is that many large institutional fund-of-funds manage retirement plans.  Their goal is to preserve the wealth of the everyday hardworking people who entrusted their savings in them.  Think about it – if you are working for SF MUNI and put your hard saved earnings from your salary into your company’s retirement plan, the last thing you want to hear is that your retirement plan lost all your money by investing in some dumbass new fund manager who invested in dogsh*t startups!  Most retirement plans will not be investing in unproven first time fund managers.

Others don’t mind losing money if there’s the potential to make above and beyond a TON of money.  E.g. you invest $10k and it has a 95% probability of being entirely lost but there’s a 5% chance that it could make $1m.

Then, there are lots of non-ROI reasons to invest.  To learn about an industry or a new technology.  To brag to friends.  To network with other investors or the founders.  Etc.  These are all equally great reasons to invest.

Most people have a blend of reasons, but it’s important to figure out what that blend is.

In our first meetings with all the investors we met with, we tried to assess what motivated each person we spoke with to get a sense of whether an investor would likely be a good fit.  (More on this later)

3) We prioritized speed over dollars

Our focus for this raise was on speed.  According to Preqin, in 2016, it took first time fund managers an average of 17 months to close a first fund.  For us, we decided that we really wanted to raise our fund in less than a year (and ultimately closed in 10 months).  So if it meant raising only $5-10m vs $10m-$20m in twice the time, we wanted to opt for less money at a faster pace.  This essentially dictated our strategy to raise primarily from individuals, because they can make decisions quickly.

The main reason why speed mattered to us is that per SEC rules, we could not market our fund while we were fundraising.  As marketers, we wanted to start actively marketing Hustle Fund as soon as possible.

4) We iterated our deck a LOT!

Storytelling is incredibly important for any fundraise.  As a new VC, we had no brand and no product to show.  In most cases, there’s literally *nothing* that differentiates a new VC from all the other fund managers.

The first version of our deck basically talked about how we had some edge because we went to “fancy” schools, worked at “fancy” jobs and were already active seed investors.  And I remember my friend Tim Chae basically looking at that slide and saying that every fund manager on the fundraising circuit had everything we had.  And he was right.  The hundreds of new VCs who are out pitching right now all went to some permutation of fancy schools and/or worked at fancy companies and/or have done some fancy investing.  These are not differentiators!

Originally posted by various-cartoon-awesomeness

We quickly realized that we needed to be able to tell a differentiated story.  For us, our biggest differentiator is around our model of how we invest – namely, we look heavily at speed of execution in investing the bulk of our fund.  This was not only a story around being different but also around why our past experience has led us to this model and why we are uniquely qualified to invest in this way.

It took us about 20 versions of our slide deck to hit this story right.  Thanks to so many people who gave us feedback on our story and especially to Tommy Leep, who helped us get our story on the right track early on.  If you get the chance to work with him on your pitch – whether you’re a fund or a startup – do it.

5) We built momentum by packing in lots of meetings.  I personally did 345 fundraising meetings between July 9, 2017 – May 25, 2018

In the past, I’ve written about how to generate fear of missing out (FOMO) amongst investors when you’re raising for your startup.  In the beginning when you have raised nothing, it’s hard to generate FOMO.  Whether raising money for a startup or a VC, no investor wants to be first check in.  So the best way to show fundraising momentum when no money has been committed is to pack in a lot of fundraising meetings.  This makes it easier to generate excitement when potential investors hear that other investors are doing second meetings with you.  And you also want all investors to end up committing to you around the same time.

Once you get commits, then you can start talking with other potential investors about those commits, which generates even more commits.  The key is that you need to constantly be meeting with people.

Here’s a graph of all my meetings per week between Summer 2017 and Spring of 2018:

Note: this doesn’t include all the meetings that my co-founder Eric Bahn did.  We often did first meetings with potential investors individually.  So collectively, our total number of meetings was much higher than 345!

You can see this Google spreadsheet of all my meetings to get a sense of what I did week to week.

You can also see from this graph that I began to run out of leads!  This is the most important thing – don’t run out of leads!  (more on that below)

6) We started with a low minimum check size to close investors quickly and raised it over time.  

In the beginning, our minimum check size started at $25k and eventually it went all the way up to $300k (for individual investors).  We did this to generate quick commits and create more FOMO.

Product startups can do this too.  I did this with my company LaunchBit — our smallest check size back then was $5k, and then we increased the minimum.

7) We qualified investors on first meeting

As I mentioned above, we were looking for investors we could close quickly.  For individuals at smaller check sizes, this often meant just 1-2 meetings.  Much like with startup fundraising, if someone was taking too long to decide relative to the number of decision makers involved and the potential check size, then that investor was probably not a good fit for our fund.  You want to be raising from people who are pretty bought into what you are doing – not people who will be an uphill battle to convince.

There were some folks, whom we met, who just were not quite ready to invest either because they were new to/not comfortable with the VC asset class or they were not yet bought into us / Hustle Fund as a first fund.  And that was perfectly fine – the important thing was just to figure that out quickly and move on and generate more leads and meet more new people.

This is really important, because I think one of the top mistakes I made in fundraising as a product startup founder and one of the top fundraising mistakes most first time fundraisers make is in spending too much time with people who just will not close quickly enough.  It’s tempting to spend time with any investor who will take a meeting with you.  And it often seems like it’s really hard to generate new leads.  But now that I’ve done this a few times, the better approach is to try to keep looking for new warmer leads rather than to feel stuck warming up cold ones.

8) We generated lots of leads (in the beginning) using brute force

Building on my point above, I think one of the top reasons founders (or fund managers) spend too much time on meetings with people who are clearly not going to invest soon is that they don’t know where to find more leads.  If you’re a product startup and you’ve exhausted a typical list of VCs (such as this one from Samir Kaji at First Republic), you’re probably wondering, “Now what?”  Where do I go now to raise money?

When I was a founder, this was certainly the mindset I had.  My perspective now, though, is that the world is filled with infinite money sources, and it’s my job to find the right matches as quickly as possible.  This mindset also takes the pressure off tremendously.  As a founder, I felt a lot of pressure to close a particular person, because it just seemed like there was a finite pool of startup investors.  Now with a more seasoned view, I feel no pressure at all, because there are actually a lot of people who are interested somewhere in the world – you just need to find them.

This means that you have to be generating a lot of leads and doing lots and lots of first meetings (see graph above).  So how did we generate leads?

We used a pretty standard B2B sales playbook to do so:

8a) Get referrals

We started by approaching friends and acquaintances and asked everyone if they were interested in investing or knew 1-2 people who might be interested in chatting with us about potentially investing Hustle Fund.  This actually allowed us to branch out pretty quickly, because people know a lot of people! And those people know a lot of people!  So even if you are starting with someone who does not have any money or is really not interested in investing in VC, just by asking for just 1-2 solid intros, you can actually find some interesting contacts.

I want to highlight the ask for “1 to 2 intros”.  The ask is NOT, “Hey if you know anyone whom you think might be a good fit” <– NO!  People will just brush you off and not think about your ask.  You want each person you meet to legitimately think about the best-fit person in his/her network out of the thousands of people they may know.  Having a specific simple ask to just think about one person in 2 minutes is a doable / realistic ask of everyone you know no matter how close you may be to him/her.

The other thing that I think people automatically assume is that in order to have a good network, you need to be someone like Ashton Kutcher and have an amazing network.  That certainly helps!  But it’s not necessary.

These are all the people I made this referral ask of:

  • Family
  • Friends
  • Friends’ families
  • Former co-workers
  • Former founders I’ve backed either in the past or present
  • People I met at events where I spoke
  • Organizers of events where I spoke
  • Where appropriate, I even asked some founders who pitched me at Hustle Fund on their businesses!

If you think about it from this perspective, if you are in the tech industry, there are so many people you can pitch / get referrals from.  Every tech worker is fair game – do you know how much tech workers make per year?  So. much. money.  Do you know how many of them know other tech workers?  Those are the only people they hang out with.  Any startup founder you know – no matter how much they are succeeding or flailing  — knows investors who have backed them or other startup founders.

On our $11.5m fund, most of it, including all of our largest anchors — special thank you to Shanda, LINE, and Naver — came from referrals – not from within our direct network of people we already knew.  Some of our investors are referrals who had other referrals.

So how do you soft pitch someone?  (and you should be soft pitching literally everyone you meet)

You know when people ask you, “Oh how have you been, what are you up to these days?”  That’s your window to soft pitch.  “Great!  I started this new fund.  These days, I’ve been, ya know, raising some money for it.  So if you or a couple friends you know are interested in taking a look, I would love to chat!“  Gauge the reaction.  If it’s positive, then try to set up a more formal meeting to actually pitch.  If it’s negative, then ask for 1-2 referrals.

Using a Cialdini-esque approach, you want to ask for the moon.  People will either fulfill it, which is great.  Or if they can’t, they feel bad and want to be helpful and will likely help you with whatever smaller ask you have.  Referrals are that smaller ask and really were clutch in helping us raise our fund.

I soft pitched everyone at every party I went to.  I soft pitched my optometrist during my eye appointment.  Under Obamacare, you now get basically a free meeting to pitch a health professional while getting a checkup.  Your doctor / dentist / optometrist / lawyer / accountant – these are all people you can pitch or ask for referrals from when you meet them (and they all have money 🙂 ).

We asked some of our closer friends for a TON of referrals (way more than the 1-2 that I mentioned above).  They were *so incredibly helpful*.  I probably owe them my first born child, but I’m not sure they would really appreciate the tantrums.

This referral strategy is a lot of work and requires a lot of meetings, but it’s a way to get started and get tapped into networks you don’t have.

8b) Throw parties / brunches / dinners / events

Some of our friends were a bit uncomfortable doing introductions for the purpose of fundraising.  Money is a funny topic that people don’t like to talk about very much in the US.  Some people view investment opportunities as opportunities and other people view them as liabilities (as mentioned above).

So, an alternative approach we used sometimes to get referrals was to ask our friends to throw parties / dinners / brunches and invite people we wanted to meet.  So, if your friend is connected to someone you want to meet, an alternative ask is to ask your friend to throw a dinner / brunch (and you pay for it) and invite both you and that person you want to meet.  Then you can soft pitch directly the person you want to meet without your friend having to feel awkward.

Interestingly enough, I found that entrepreneurs and investors were very comfortable doing direct introductions for us, while my friends who have always worked at big corporate jobs (and have never raised money before), were less comfortable.  And that’s ok.  The party / dinner / brunch route is an alternative path to the same result.  We ended up attending a lot of lunches / dinners / events that are not reflected in the meeting-count on the graph above.

In addition, we also threw a lot of dinners / talks / parties / events ourselves, and we invited both people we were talking to and committed investors to those events.  These events were helpful in closing investors as well.

Talks at conferences were also a good way to show off knowledge and give people a sense of how we thought about investments.  We have ended up meeting a number of potential LPs from events and conferences where we gave talks.  Events allow you to be “thought leader”.

8c) Do your own pattern matching

Once we started getting investors, we noticed some patterns emerge.  Even though we had focused our raise primarily in the Bay Area and didn’t travel much, a lot of our investors are from outside the Bay Area.  We conjectured that there might be much stronger interest outside of the Bay Area, where access to tech startups, is limited.

As it would turn out, almost half of the money in our fund comes from Asia (not Asian Americans but from Asia-Asia) even though we didn’t make any trips out there.

But patterns can also be thesis-driven.  Another pattern we found for Hustle Fund was that anyone who had been a mentor for or a manager of an accelerator really resonated with our thesis and invested in our fund.

It might be worth honing in on a pattern and trying to find as many people who fit that pattern.

Speaking of patterns, one interesting side note observation is that we had really poor success in converting female investors (despite actually investing in a lot of female founders both in the past and with Hustle Fund).  In Hustle Fund 1, < 5% of our investor base is made up of women.  (Defined as: we spoke with a woman from that entity or household). But we have pitched both men and women.  I’ve had many other friends who have raised money for funds or startups who have noted similar observations – women are seemingly much more conservative with their investments.

Just as a side tangent: it’s fine if people – men or women – don’t want to invest in Hustle Fund per se.  But, if professional women with some level of means are not taking some financial risk, they won’t achieve the same level of financial success as their male counterparts.  Think about this – we talk everyday about how women don’t make the same amount as their male counterparts at all these tech companies.  But we don’t talk at all about how women are left behind on investments.  Every rich person knows that you don’t make money on salaries – you make most of your money on investments.  If you were in the seed round of Dropbox or Google with just a few thousand dollars invested, you wouldn’t even be concerned about a salary.

8d) We made a video

We made a video (see hustlefund.vc) to explain who we are.  This was a bit of a gamble, because we spent $13k(!) all in on producing this video.  That being said, we thought it was worthwhile, because we believed we could stand out if we did the video well.

This gamble has paid off in spades.  In part, I think it’s because no other VC (that I know of) has a video on their website.  So it may be worthwhile to pay for an asset that no one else has in order to stand out.

9) Your richest contacts are not necessarily your biggest checks and vice-versa

Building on a prior point about soft pitching anyone and everyone is that it turns out there was no correlation between wealth and check size.

This was an interesting learning for us.  In the beginning, we made a list of our richest friends and how much we thought each could invest.  We were so wildly off in meeting these numbers.  On the flip side, some of our friends who are not super rich surprised us and invested substantially.

There are so many reasons for this.  a) Making a lot of money in itself doesn’t mean that people have a lot of money.  They could have a big mortgage.  They could spend a lot of money.  They could have a lot of capital tied up in other projects or investments.  b) There are also a lot of people who don’t make a lot of money but are very good at saving it and investing it and secretly have a lot of wealth.  The Millionaire Next Door is a good illustration of both of these points.  c) Some people come from wealthy families and you just have no idea that they do.  d) People also have varying levels of bullish-ness on you, your thesis, and your asset class.  People also have varying levels of risk / reward tolerance.

It’s also important to note that sometimes people who are not / don’t seem like angel investors can become angel investors for you.  Andy Cook talks about how he brought in new investors who had never invested in startups before into his round.  We did the same as well.  Just because someone isn’t already an angel investor doesn’t mean that he/she couldn’t be.

This is why our grassroots strategy of taking so many meetings worked so well – we just never knew who would actually be interested in investing.  And we could not find any way to qualify people apriori.  This is why it’s so important to pitch anyone and everyone – it’s hard to know who will bite and who won’t.

10) We used a CRM to manage our process

This process requires a CRM, because you need to make sure that leads are not being dropped through the cracks.  We invested in using a CRM right away to track conversations to move people through our pipeline.

This also made it easier for Eric and me to divide and conquer – we would take our own meetings with individuals and regroup for second meetings and beyond.  And we could both see who was talking with whom so that we didn’t start different conversations with different people from the same fund or approach the same people.

More importantly, it was critical that we maintained discipline over all those months to keep the CRM up-to-date.

11) You’re not hot until the end

This applies to both startups and funds.  Fundraising is always a slog in the beginning, because you’re trying to generate lots of leads and qualify them.

This is a graph of what our fundraising looked like:

The blue line represents our soft commits over the months (verbal / written email commits).  The red line represents money we actually closed legally (signed docs).  As always, “soft commits” are a bit more ambitious than actual commits, but in the end, they should converge (or come close).

As you can see, we averaged getting about $1m per month in soft commits for the first 6-7 months to get up to around $6.5m in commits, which we closed in Dec 2017.  If you follow the red line, you can see that there is a surge of $5m at the end, which literally came together in the last couple of months of our fundraising process!

Like almost every raise I’ve seen, you’re just not hot until the end.

12) This all sounds easy but it takes hustle AND a village to do this!  

The fundraising process I’ve outlined above is executable and accessible for anyone.  And it actually sounds easy.  Just do a bunch of meetings and ask everyone for intros or money, right?

But wrapping up this post, I’ll leave you with a couple of final thoughts.

12a) It takes lots of hustle and lots of meetings to get this done. 

Last July (2017), when my new baby was about 7 weeks old, I decided to quit my prior job in the middle of my maternity leave and started Hustle Fund shortly afterwards.  That summer, during the day I would leave him with my parents, and I would go from meeting to meeting, stopping to pump milk in SF parking lots or at large tech companies’ mothers’ rooms.  At night, I would work on decks and update our CRM.  I would sleep about 4 hours a night sporadically as the baby would wake up every 2-3 hours to drink milk.  I got through most days on lots of coffee and adrenaline.  But no matter how tired I was, it was important to go into each and every meeting just as excited as ever.

I don’t mention this schedule to “brag about my hustle,” but just to paint reality – it really does take a lot of work to do lots and lots of meetings.  It’s important to work smart, but for some things, as smartly as you work, there is no shortcut for just lots and lots of hard work.  And know that as hard as it is, you’re not alone.

12b) It takes a village to really go anywhere. 

To start this fund, I leaned on a TON of people.

While this small section here doesn’t do justice to my gratitude, I did want to highlight just how many people my awesome co-founder Eric Bahn and I roped into this raise.  (I’m also incredibly grateful to have a fantastic co-founder in Eric and now Shiyan Koh!)

  • Our ~90 investors in our fund (they occupy way fewer LP slots but there are at least 90 individuals / spouses / family members / companies and people with a stake in this)
  • Past founders I’ve backed who have introduced me to their investors; one successful founder even generously offered us her PR agency and offered to foot the bill!
  • Current founders who went through their rolodex in trying to help us connect with their other investors / VCs / rich friends
  • VC friends who supported us with personal investments / investments from their funds / intros to their investors
  • Friends and family who came over to my house to cook food / bring over take out / buy us food – it was pretty incredible not to have to worry about food for a while
  • Friends and family who housed me in their spare bedroom or their couch on my fundraising trips since we have limited budget
  • Friends and family who introduced me to all kinds of rich and well-connected people
  • My blog readers who introduced me to their network
  • My own immediate family who took care of my kid(s) every week for months!
  • And big props to my spouse JJJS as well as Eric’s spouse and Shiyan’s spouse for really bearing the brunt of all the work that goes into starting a fund.

There were literally hundreds of people who helped us get this thing up and running (and we are just at the beginning).  And I’m so very thankful to all of them for their generosity.

Fundraising is hard.  And it takes a long time.  But don’t give up.  Happy holidays!