Tactical fundraising by Elizabeth Yin

Dear elizy: I’m a solo founder…do VCs fund solo founders?

Dear elizy: I was wondering if you would mind giving some insights on startups with a small team (in my case, the sole founder) and are looking up to scale up the business? Would you recommend growing the team first and then consider fundraising? Do you think VCs would be happy to fund a startup with a sole founder? Or would VCs think the startup is not capable of acquiring quality teammates?

– Flying Solo from Hong Kong

Dear Flying Solo: Great question! Unfortunately, it really depends on the investor. There are some investors who adamantly will not back solo founders because they think it is just too hard to start a company alone. Then there are many others who do not care.

At 500 Startups, we don’t care whether you are a solo founder. Solo founders aren’t given a break – they are expected to achieve as much as companies with multiple founders, which inherently makes it harder to be solo. That being said, we have backed a number of solo founders over the years who have gone on to do quite well.

Here are some examples of successful companies that have been started by solo founders. Techcrunch created a report suggesting that many VCs will back solo founders.

As far as raising money goes, every early stage VC is looking for “big ideas with big markets” (subjective) and strong teams. So having a strong team – regardless of whether your teammates are co-founders or employees – will be important in raising money. Unless you have a strong track record, it’ll be difficult to raise money with no teammates.

To attract such strong teammates, unless you have a great network, often you’ll need to show some execution progress on your idea to show that you are serious about your business and worth teaming up with.

Given where I think you are, I would recommend starting with whatever team you’ve got now (sounds like it is just you?) and work towards product/market fit. In parallel, for skills that you are deficient in, I’d start looking for someone with that skillset and use your progress on your business as a way to demonstrate commitment. This person may eventually evolve into a co-founder or may turn into an early employee. In my mind, the only difference between a co-founder and an early employee is the level of equity and control on the company. So whatever you do, don’t rush into teaming up with someone who has significant equity and control if you’re not 100% sure about him/her in terms of skillset-fit as well as compatibility-fit.

Good luck!

Today we go back to work

I haven’t really been into politics since college. Yesterday, I cast a vote for the first time in 8+ years, and today, I’m disappointed in our country. It isn’t right to have a president who has:

Screwed over numerous business partners, customers, and employees and workers
Made countless racist, sexist, homophobic, xenophobic comments including (but not limited to) calling Mexicans rapists, and would like to ban people of a particular religion from immigrating to the United States
Bragged about committing sexual assault and has been accused by multiple women of committing sexual assault

I have deep faith in our country. The US, like most of the West, has enjoyed, for centuries, a legal infrastructure that is the foundation of our businesses and industries. This is what has allowed entrepreneurship to thrive in this country. Contrary to what many say, our recent election doesn’t alter America’s long-term prospects, but in the near term, we are in trouble.

Regardless of your politics, Donald Trump’s ethical and moral deficiencies are concerning and disappointing. My fear is that this country will devolve, that this country will somehow see Donald Trump as a role model and think that it is OK to screw over people, to be divisive, and to sexually assault others.

It’s also days like these when we rise up as Americans and remember why we do what we do. No matter what is happening in the public sector right now, today we go back to work. As a bi-product of our work, we will continue to combat these things.

Today, we go back to work to continue building, investing, and coaching technology companies that change our lives and society for the better. We go back to work to continue to level the playing field for all entrepreneurs, regardless of race, gender, sexual orientation, nationality, or pedigree, in order to not only build a better society but to bring about progress and technology for all people and not just a select few. We continue to be more inclusive rather than divisive and judge business ideas, business partners, employees and contractors on their competence and character rather than on what they look like or where they’re from or whom they love.

Today, we go back to work to continue to chip away at the bizarre power dynamics that may often exist in industries, such as in tech and investing — to abolish sexual assault, sexual harassment, and even just pattern matching by what people look like and not on the basis of character, grit, and results. It makes me angry that I’ve heard too many cases in this industry this year alone, and yet, few will talk about it openly. We need to be more vocal about this to move our society forward rather than sweeping issues like these under the rug.

We have a lot of work to do; let’s continue to make progress.

Cover photo by Luke Stackpoole on Unsplash

How does pedigree affect fundraising?

It really pains me to write this post… but it has to be said. I was comparing my small personal angel portfolio and my investments at 500 Startups, and I noticed that on a percentage basis, the companies in my personal portfolio have been able to raise more money on average and more easily than companies in my 500 portfolio.

Why is that? My thesis in how I pick companies remains the same across both portfolios. All of the companies I pick are at roughly the same stage — all seed companies who have launched a product and have some semblance of traction, though this ranges quite a bit.

The #1 difference between my personal portfolio and my 500 portfolio is that my personal portfolio consists of all friends’ companies. And, all of those founders have pedigree. They haven’t necessarily had past earth-shattering success, but they went to elite schools. They worked at elite places, generally at fast-growth unicorns. One group isn’t necessarily smarter than the other, but the branding on people’s resumes have made all of the difference.

(Update: A reader asked me if I’m perpetuating the problem by only personally investing in founders with pedigree – great q, and see the comments below for the clarification on this.)

Here are just a couple of data points:

Take Company X, for example, in my personal portfolio. They have limited traction, especially given they’ve been around for nearly 2 years. They are in a space that is a bit crowded. I erroneously thought that it would be really difficult for them to raise money, but it was a walk in the park. They raised $3m+ with a whole group of name-brand investors!

Then take Company Y, a 500 company I’ve worked closely with for the last couple of years. They have really great traction and high consistent growth for as long as I’ve known them. They, too, are in a space that is a bit crowded. The team isn’t from the Bay Area, and they are college dropouts (but not like Bill Gates or Mark Zuckerberg). That said, they are really clever founders. Despite their results, it has been very tough for them to raise. They have raised some money, but it has been way more difficult than it should have been given that the business has great unit economics and results.

A few thoughts on all this:

1. Knowing all of this, the way to get quick markups is to just invest in a lot of teams with great pedigree. In the short term, this is how to show that your portfolio is doing well!

2. But in the long term — say several years, I wonder how the two portfolios will compare? My fear for Company X is that fundraising has been so easy for them, they won’t be able to achieve the traction they’ll need to raise a Series A. Investors may go gaga for their team pedigree now, but at the series A, they will not get a pass — they will be expected to show results. My fear is that they will be not be hungry enough to move quickly to hit series A benchmarks because they don’t realize the game will be different for them at the next round. Companies that have an easy time fundraising in the beginning tend to think that’s how it will always be. And this is dangerous thinking. If you’re in this situation, you should be very cognizant of this.

3. For my companies who don’t have founders with brand names on their resumes, my fear is that even if they have great businesses and can kinda bootstrap, they will be a bit undercapitalized. They need to be above-and-beyond persistent in getting to know investors so that they can bring in some money over time. Even if it’s tough to raise money now, eventually, business metrics will trump everything else at the later stages; that’s what investors will care about then. Founders who don’t have pedigree but are running great businesses will do better at fundraising later. So, if you’re in this camp, just hang in there.

At the end of the day, doing a startup isn’t about how much money you can raise. It’s about running a great business, and I’ll need about a decade to tell you which of my two portfolios has done better. But, you can’t deny that companies that can raise money are better equipped to compete. It troubles me that the elite truly have a leg up in raising money. When you think about it, this cycle continues because if investors want those fast markups to help raise their next fund in a couple of years, they should definitely invest in founders with pedigree; they will have great unrealized gains to show potential limited partners.

I truly believe in looking for strong business fundamentals and also believe that great founders come from all walks-of-life. And yet, when I make a bet on teams without pedigree, unless they are in a hot space, I know that they will have a really hard time raising money in the short term (and it will affect my short-term IRR as well). In these cases, I have to believe these founders have enough hustle to survive a long time with limited resources while accomplishing significant results. And if I don’t see the hustle and determination, then I just really can’t make the bet.

Wrapping this all up, I don’t have any solutions, but this is a serious consideration for the industry: how do you level the playing field for entrepreneurs?

Why investors are like sheep (and how to herd them)

A fun little post for Halloween. In many ways, a lot of investors are like sheep. Not all. But many.

Hopefully they are not like this:

I don’t know what sheep like to eat, so let’s say they like ice cream (I mean who doesn’t?) Let’s say you are selling ice cream cones, but other entrepreneurs are, too. It can be easy for sheep to get paralyzed when deciding whom to buy ice cream from. There are just so many options.

This can be frustrating if you’re trying to sell ice cream.

So you start by telling one sheep, “Hey, I have a limited amount of ice cream…wanna buy?” Then you say the same thing to lots of other sheep.

Then, a bunch of sheep are now closer to your ice cream truck, but they are not buying your ice cream because they are still deciding whether they want your ice cream or someone else’s. This is OK and perfectly normal. At this point, there is no need to put a ton of pressure on any of the sheep until you have enough sheep moving your general direction. This means you need to take a lot of initial meetings with a ton of sheep.

Soon you’ve got some semblance of a herd around your ice cream truck, but no one is buying yet. So, you start to put more pressure on all of them: “Hey, I’m starting to have final conversations with a bunch of sheep. If you are truly interested in my organic, gluten-free, tasteless ice cream, we really should talk in the next couple of days.”

At some point, you need to tell all the sheep, “I’m in final conversations with ~20 sheep about buying my ice cream but only have enough ice cream for ~10 sheep. Can you let me know if you’re in or out?”

This is a risky move, but at some point you may just need to do this to round up as many sheep as you can. In fact, your lasso (do people use that for sheep?) may end up missing everyone! You may not end up with any sheep buying your ice cream, but if none of the sheep hovering around your ice cream truck is biting, you may just need to take that risk.

Sheepishly, this post may have made everything more confusing. But, what do I know? I’m not actually a sheep…

Happy Halloween!

Cover photo by Sam Carter on Unsplash

The best days and worst days of investing

This post isn’t for you. You are probably trying to get your round done and this post won’t help you with that. This post is mostly for me. Sorry.

Two years in, people often ask me what it’s like to be an investor, what I like and what I don’t like. There are a lot of things that I think are wrong with the VC industry (and I could talk about that for 20 posts). Focusing on the activity of investing itself, these are my best and worst days.

The worst days

The worst day as an investor are the days when you need to reject entrepreneurs. Last week, I had to send out rejection letters to everyone who didn’t make it to 500′s seed program, which just started. We have a limited number of spots, so by definition, not everyone is going to make it. Every batch, I procrastinate on doing this activity.

There are a lot of great businesses that we just can’t invest in (for now).

That’s just the unfortunate truth. Even though we do a lot of investing, we just can’t invest in every good business. There are also business models that we just can’t invest in — for example, we don’t invest in brick and mortar businesses. That’s just not what we do. Similarly, we don’t invest in gaming or pharmaceuticals. We just don’t have an understanding of these areas.

In addition, because there is always limited capital to deploy, we have to pick companies who can best utilize our investment now. In many cases, this means that we need to turn down companies that are not at the right stage, even if the founders are really smart, tenacious, and awesome. We just can’t get involved in many businesses at this particular time. That bums me out, but it’s business.

When we send rejection emails, the above thoughts don’t often get conveyed. Having been rejected by lots of investors before, I have previously thought, “Oh, they didn’t like me,” or, “They think my business sucks,” or whatever. It isn’t necessarily that at all. It could just be that this isn’t the right fit or the right fit right now. Whether you are getting a rejection from 500 Startups or someone else, it is still worthwhile (if you want) to reapproach an investor. If anything, investors who have spent more time with you rather than less are more likely to be your advocates, because they have gotten to know you.

Originally posted by perfectlyimperfectok

The best days

The best days, though, are the days when I get to talk with entrepreneurs, and they leave feeling inspired.

This doesn’t happen all the time (or perhaps even most of the time), but it’s a great feeling when it does happen. This happens with portfolio companies and even in meetings with entrepreneurs who are pitching their business to me. The best example that I have comes from my own experience when I was an entrepreneur. I remember talking with Jason Lemkin about our customer acquisition process at LaunchBit. I was telling him about the outbound sales methods we were using. It was working; my cold emails were effective. But, it wasn’t scaling well. He had a particular insight about structuring the roles on our team, and that was an “aha” moment for me. I walked away from that meeting feeling super pumped.

As an entrepreneur, you often feel down in the dumps. Lots of things are not quite working or not quite working well. You may be so close to making something about your company really soar, and yet you often feel so far away and may even be tempted to throw away whatever is sorta working. Inspiration comes from the meetings where you get some interesting insight that you can put to work right away that will have a huge impact on your company. As an investor, I love being able to provide that or even just some encouragement. If an entrepreneur walks away feeling either super pumped or a little better about themselves / their business, those are the best days.

Cover photo by Patrick Tomasso on Unsplash

How do seed investors benchmark startups?

Understanding how investors benchmark different kinds of companies is all very confusing. When I was an entrepreneur, I had no idea how this all worked. How does a social app such as Snapchat get funded as compared to, say, a developer tools company like New Relic? Obviously, their milestones and KPIs are very different.

In this post, I’m going to very simplistically dive into some high level categories and talk about how early stage investors consider each. In my mind, I’ve divided companies into 4 categories. This is not an industry standard — this is just how I personally see things. However, most early stage investors probably think along similar lines:

Super high-tech companies
High infrastructure companies
Free consumer apps
Everything else — aka companies that can make money immediately

There is a lot to say for each category, but there isn’t enough space to do so here. (Disclaimer: all of this really only applies to software investors).

Super high-tech companies

I think a lot of software companies would like to think they belong in this category, but the reality is that most software products are pretty easy to build. Even the vast majority of all those “AI” and “big data” and “machine learning” pitches that I see are not in this category. Open source libraries (such as TensorFlow) make technology more accessible for less-skilled or self-taught developers such as myself to use. A lot of previously “super high-tech” ideas are no longer that high-tech.

So what is in this category? Essentially, my definition for companies in this category is that the technology is so difficult to build that only a small subset of people in the world can build it. As a result, this is a constantly moving target. I suppose the way that I actually benchmark this in my head (just to be perfectly candid here) is by asking myself if a product is something that, as a mediocre self-taught developer, I could personally teach myself to build within a year. If the answer is yes, then it’s not really that high tech. And it turns out a lot of ideas are just not that high tech. (There are just a lot of things you can learn these days on YouTube and by Googling…)

: Originally posted by genniside

As a result, the most important criteria in this category is the team. To be more specific, I’m talking about the team’s backgrounds. The team is important in every category, but for super high-tech companies, it is extra important that it is the right team to accomplish the particular idea. Teams that thrive in this category have strong and often niche backgrounds in whatever it is they are doing. For example, in the self-driving car category, most of the teams that stand out have previously done a PhD in a related topic, participated in the DARPA Grand Challenge for a few years, or have worked for a company (e.g., Google) on a self-driving car or vision-related project. If you are competing in this category, your team’s resume, or pedigree, is really critical — more so than anything else. You don’t see a lot of “self-taught” folks in this category.

High infrastructure companies

Traditionally, software investors have loved being in the software industry because the capital costs are low and because you can get something to market quickly. However, a lot of software investors are now dabbling in fields that don’t necessarily have these characteristics. Investors are pouring a lot of money into health and fintech companies even though many of these companies have a number of hurdles to overcome. Getting licenses, FDA approvals, etc. are not trivial, but they are also barriers to entry for would-be competitors.

As a result, for these kinds of businesses, investors often don’t expect that companies can earn revenue right out of the gate because they may not be able to do so legally. Similar to the super high tech category, investors often look at the backgrounds of the team very closely because understanding clearly what needs to be done is really important. Has the team worked in the same area prior to starting the company? Is the company already in the middle of overcoming regulatory hurdles? Does the team know exactly what they need to do to go into business? These are some of the most important criteria for investing in seed-stage teams.

Free consumer app companies

In contrast to the last two categories, successful founders of free consumer apps tend to come from any background. Companies in this category include companies like Twitter, Facebook, Instagram, Pinterest, and Snapchat. These are all companies that need a TON of users, great retention and engagement, and continued-fast-growth of user adoption in order to make money off of ad revenue later.

If your startup is in this category, you’ll need to craft a story around the following:

Hypergrowth
How this hyper growth is happening organically. Do you have virality built into the product? How do new users find your product without your having to pay money?
High engagement. Users spend a TON of time on your platform, app, or site. When Facebook first raised their seed round, investors were compelled by just how many hours per day their users were using their platform.
High retention rate

In fact, the business model matters very a little. Most investors who invest in free consumer apps don’t particularly care about monetization at the early stages. But you need to be growing FAST. Really, really fast. Investors just want you to keep growing quickly and retain and engage these people. (Of course, you should also be able to articulate at least a high-level plan around future monetization.)

You’ll want to show that you are making progress on optimizing your free customer acquisition funnel (e.g., growing quickly) and that you are also improving stickiness over time.

The thing about this category is that it’s HARD. I mean REALLY HARD. Growing a business is already quite hard, but for free consumer app categories, there are a couple of things to consider:

1. Because you are not monetizing, if you are unable to fundraise, it becomes difficult to keep the boat afloat.

In the beginning, this may not be a problem — you can bootstrap. However, once you get to, say, a series A or B level and have say 30 people on payroll, if you cannot raise, it’s really difficult to bootstrap a company of that size.

2. The fundraising landscape gets more competitive as you progress.

Generally for all companies, going from the seed to the A to the B rounds is difficult. The number of series B investors is way smaller than seed investors. It is even harder for free consumer companies because there are even fewer “free-consumer investors.” In this category, you are competing with other pure-consumer apps who may be doing something different but are vying for the same consumer attention. Certainly when it comes to competing for fundraising dollars, you will be benchmarked against other free consumer apps on user base and growth of that engaged user base.

“Everything else” companies

Lastly, there’s everything else. The vast majority of pitches that I see tend to end up in this category. These are products that can and should generate revenue right out of the gates in both B2B and consumer ideas. Obviously, there are a LOT of verticals within this category that are looked at very differently — everything from e-commerce to B2B SaaS to marketplaces. What specific things investors look for very much depend on the particular vertical and business model, and that is a topic for many more blog posts. But the one commonality amongst all startups in this category — regardless of vertical — is that most investors would really like startups to start monetizing right out of the gate.

Team backgrounds matter in the “everything else” category but not nearly as much as in the first two categories because anyone can start a business in this category. Instead, execution and traction are often a measure of the team rather than their resumes.

I’ve outlined these categories because it can be rather confusing as an entrepreneur to know what you need to achieve in order to get funding. On one hand, you may see friends in fintech getting funded when they have zero traction, and on the other hand, if you’re in e-commerce, you may need to hit $1M GMV runrate to capture that same investor’s attention. It just doesn’t seem to make sense. Hopefully this post illuminates why investors think along these lines.

Build a product that fits your runway

What product you should build as an entrepreneur should, in large part, be based on your runway. For example, very few entrepreneurs could have built Tesla because most entrepreneurs are neither super rich nor able to raise tons and tons of money right out of the gate. This seems pretty obvious.

Everyday, I see entrepreneurs trying to build products that are way out of the scope of their runway. For example, if you are trying to build a new type of email marketing tool, you will need to have a completely different approach from what MailChimp does because you will not be able to afford to build out all the features of a full-fledged traditional email marketing system. It would take years to go head-to-head with their features. Similarly, if you are looking to build out a CMS, you should not even consider trying to incorporate all the features that Weebly or WordPress have because they have developed features that took years to build.

Now, does this mean that should not build a product in an existing space at all? No. But, it means that you need to really think carefully about how to build a simple and quick-to-build product that will compete in an existing space through strong differentiation. SendGrid (500 Portfolio company) is a great example of that. They didn’t build out (at first) all the typical features of an email marketing solution. They were an API that sent mail. That’s it. No interface, no WYSIWYG features. And that was enough. They took one aspect of a traditional email marketing solution and blew it up. Hubspot, too, in the beginning, was just focused on helping people write content. Back then, they didn’t have emailing features or a CRM or anything. This all took years to build. The initial version of the product was based on the hypothesis that they could build a simple tool that would ride on the new wave of content marketing. It’s only now that they compete in the traditional marketing automation space.

Don’t use most of your runway on product development

One of the biggest mistakes I see entrepreneurs make is that they spend too much time on product development. Part of the reason is that the scope of products are often far too complex for the first iteration. It is much better to take just one feature and blow that out of the water. Make it super simple and easy to use, and do this within just a fraction of your runway. If you’re a first-time entrepreneur without much easy access to capital, you should be shooting to get this done in < 2 months. If you can’t get it done in this time, your scope is probably too big.

There are lots of big problems that small features can solve. This is often easiest to find in products (of existing dinosaur players) who have built up bloated software. Craigslist is a good example.

Take one of these large bloated products or companies, and write down a full list of every single feature or thing that the product achieves. From this list, there are often several features that could be standalone products in themselves.

Find balance between painting your vision and explaining your current product

For all these reasons, I hate it when VCs say, “Is this a feature?” Yes! In order for you to have survivability in the beginning, your product really should feel like just a feature. But it doesn’t have to stay that way.

When you pitch your company, it will be very important to walk a fine line between conveying your vision and how things are today. Explaining the ins and outs of your current product is going to be un-inspiring, but talking too much about the future will make it seem like you’ve done nothing, or worse yet, an investor will think you’re lying if he/she finds out what your product actually looks like.

When you talk about your vision, you should be explicit in mentioning that this is how you see the future and where you see your company going. Make sure to tie your pitch back to where you currently are and the steps you need to tackle to fulfill your vision.

Why asking for advice when you want money is bullshit

Founder: And then that angel investor said, “This is definitely interesting. Lemme intro you to these two people.” This has happened 3x in the last 2 days but none of these angels have written a check – is this bad signaling?

Me: Oh, not necessarily. Angel investors are not professionals, so it’s not necessarily bad signaling since they may not do many investments. Unless you’re talking about a really prolific angel. Did you ask him to invest?

Founder: I didn’t ask because I thought that if they actually wanted to invest, they would ask? We went with the strategy of asking all of the angels we were in touch with about “advice on fundraising” with the idea that the conversation would naturally transition to an investment if they were actually interested.

Yeah…

So here’s the old adage in its entirety: If you ask for money, you’ll get advice. And if you ask for advice, you’ll get money.

The truth is, this adage sometimes works…but more often than not, it doesn’t. If you are fundraising in America, you really should be asking for exactly what you want – ESPECIALLY WITH ANGEL INVESTORS.

Let’s dive into this more. (And feel free to jump in the comments to tell me how wrong I am… :) )

1. Angel investors don’t see themselves as investors

They really don’t. And this becomes more and more true everyday. Why? Because now on sites such as AngelList, you can plop down $1k into a syndicate, and even if you do 10 deals a year, you’re still only investing $10k a year – just like you might into your 401k plan. These angel investors are really just everyday upper middle-class people. Mostly tech workers.

First and foremost, angel investors see themselves as whatever their profession is. So, let’s say you ask for advice from a UX designer who is doing, say, 5 deals a year; you’re going to get advice about your design. He/she isn’t going to think of it necessarily from a fundraising perspective. This is especially true if you’re talking with other entrepreneurs who happen to be angel investors. Flip the situation around: if someone thought you were rich and came up to you asking for advice, you’d think they wanted advice, right? You wouldn’t just start throwing money around. It’s really no different as you climb the entrepreneurial success ladder.

For VCs, it’s their job to invest money. They can’t take the fund money and use it towards non-investments. But angels – it’s their money. They are not necessarily going to use it towards investment-related activities. They could buy a boat. Or a car. Or redo their backyards.

Even if someone presents an exciting opportunity in front of them, they may not even be thinking about investing their money. You need to be clear about what you’re looking for so that an angel investor doesn’t have to try to infer the situation.

2. Many angel investors write small checks and are not going to initiate a conversation about your round

As a follow-up to #1, many angel investors write small checks, and so they are not thinking about starting your round. It doesn’t mean that they would be averse to writing a check earlier in your round, per se, but they don’t really want to negotiate terms with you. They also would prefer that there are other people in your round so that you have enough capital to achieve your milestones.

Unless you dive into the weeds around your fundraising – i.e. explicitly talk about your round and who is in and all that jazz – angels would just rather avoid the headache.

3. Angel investors don’t want to have an awkward conversation with you

Which leads me to my next point. VCs already beat around the bush and hate saying uncomfortable truths because they don’t want to ruin potential financial opportunities down the road with you. But angels are even worse. They are not used to delivering tough news or feedback, since it’s not their job. They want to be your friend. Heck, in many cases, angels may be your friend or your friend’s friend. It’s just awkward to talk about fundraising. Here are some awkward things about fundraising that they may want to avoid thinking about:

You may not want them in your round since you didn’t ask, and so they won’t ask you about your round

You may have too high of a cap, and they don’t want to express interest in your round only to back out
You may not have enough traction (either fundraising traction or revenue traction), and it’s awkward to ask about traction if you’re not a professional investor

All in all, I would just come out and be explicit with what you’re looking for. Now, I know that it can be awkward to ask for money or ask someone to look at your round, so here are a couple of phrases that might help you out:

Hey – since I know you do some angel investing, I wanted to get your thoughts on our round…
I’m curious if this is the type of angel deal you might be interested in?

Would love to know what other people’s thoughts are on this topic. Feel free to comment below.

What I’ve learned from seeing 20k company pitches

I just passed my two year mark at 500 Startups. The other day, my colleague asked me how many company pitches I’ve personally seen. When we were calculating it out, it came out to about 20k!

To be fair, this number includes pitch emails like this (including a response from my former colleague, Sean Percival).

(In fact, the vast majority of pitches I’ve seen probably fall under this category, and these only take a few seconds to read and archive. This is how you get to see 20k pitches!)

That being said, it’s been quite a ride to see so many pitches in just two years. Here are some learnings and what I immediately think about when I see a pitch:

1. Ideas are a dime a dozen…and it’s important to stand out.

As an entrepreneur, you think your idea is unique. If you’re still in the early stages of your entrepreneur-education/journey, you may even think you need to protect your idea and not share it with anyone. Even if you’re in the later stages of being an entrepreneur, you still feel like your idea is unique or at least maybe there’s only one or two other companies out there like you because that’s what you read about in TechCrunch.

It turns out everyone has the same ideas.

This isn’t a bad thing, but it means that you need to go in with the mindset of figuring out how to stand out. The good news is that if you’re making progress on your business, you can show that you’re executing. Most entrepreneurs overpitch their ideas but underpitch how they’ve been executing (revenue, traction, setting up infrastructure, etc.). This can set you apart because the vast majority of businesses I see at the seed stage are just ideas with no action.

2. Speed matters.

Not only is it important to show what you’ve done, but if you’ve been executing on a fast time scale, then that’s even more impressive. At the seed stage, there are companies who have been around for 5 months and others for 5 years. You are not only being benchmarked on hitting milestones but also on your pace.

This is one of my favorite startup presentations of all time on going fast by Mike Cassidy. Demonstrate that you can pull the trigger on things quickly — whether it is getting customers, hiring and firing employees, or product development. Convey this in your pitch.

3. If you are in a super competitive space, it’s important to address competition upfront.

If you are in a super competitive space — areas like cleaning or food delivery, for example — it’s going to be harder for you than you can ever imagine, even if you are making progress quickly. In these areas, investors are not just seeing a handful of companies doing the same thing but hundreds or thousands.

To give yourself the best shot at getting noticed, you need to do 2 things:

Demonstrate immediately — not at the end of your pitch — that you are aware that there are other businesses like yours. This shows that you have thought about the competitive landscape, and despite knowing that it’s competitive, you believe there is an opportunity for you to outcompete all other companies.
Being in a competitive space isn’t a bad thing — Google was like the 8th search engine to enter the scene, and they turned out OK — but you need to address the landscape.
Address where you fit into this landscape. This is about really understanding how you are different from the other players out there.

For example, I was talking last week with a company that is a new type of job board. They showed me their problem slide which said something to the effect of, “There are so many people who are unemployed and so many employers who cannot find good talent…blah blah blah.” Online job boards have been around for a couple of decades and even today is an incredibly competitive space! Everyone understands this problem. So, this is not the correct problem to outline in this pitch. The right way to outline this problem is to tell me why existing job board solutions suck or are ineffective and to be super insightful into the nuances of why this is the case. After that, present a differentiated solution that doesn’t have these same nuanced issues. In some sense, if you are in a crowded space, your job is to say, “The problem is that Companies A, B, and C suck, and here’s why.”

If you can do this, this will help you at least get attention on your pitch.

3. I treat referrals and cold-emails the same (for the most part).

In the beginning, I thought referrals from others would be much higher quality than companies emailing in cold. Sometimes this is true. Often it’s not. It depends a lot on who is giving the referrals. It would turn out that “famous” investors referring companies don’t necessarily refer better companies, and founders don’t necessarily refer great companies either. A lot of founders are doing favors for their friends by putting in a good word. On the flip side, there are some people whom you wouldn’t have heard of whose referrals I value the most.

So, in the end, it’s a bit of a wash, and this is why I think you, as an entrepreneur, can now write cold emails effectively to capture the attention of investors.

4. How people present themselves in pitch emails tell me if I should NOT take a meeting

I use pitch emails as a good proxy for finding the most on-point, sharp founders. Really, I can’t tell immediately who is on-point and sharp, but I can tell who is not. Meandering email copy is not a good sign. Bad spelling and lack of punctuation = also not a good sign. Bad grammar is excusable if you are a non-native English speaker, but if you are a native English speaker, that’s inexcusable. Use a company domain name as opposed to a Gmail, Yahoo, Hotmail, or AOL email address. Otherwise, your business doesn’t seem serious enough yet.

These all seem obvious and not worth addressing, but you’d be surprised just how many pitches have basic mechanical issues. If you are not good at paying attention to detail, ask a friend who is good at that to help you proofread. Getting in the door with your best foot forward is so important because it’s easy for your email to get ignored or lost.

Use bullet points when possible rather than paragraphs. They are easier to read. Bullet the key awesome things about your business. Here are some example bullets:

Revenue: now at $15k MRR, growing 30% MoM
Monthly churn is < 1%
LTV to date is $700; CAC via blended paid channels is $250
Pilot customers include Samsung, MSFT, and Oracle
CEO previously founded a marketing tech company and sold it to Marketo; CTO previously worked as a software engineer at Google X; have worked together for 2 years

If you are sending a deck, refer to this post, “The ideal email deck.” Your email is just to pique interest in getting a meeting, not to get an investment.

There are a ton of other learnings from having done this job for the last two years, but these are the things that come to mind when I see pitches.

My 5-100-500 rule to close your seed round

Here is a typical conversation I have with a portfolio founder just about every week:

Founder: I’m having a tough time closing our round.

Me: How much are you raising, and where are you now?

Founder: I’m raising $1m, and we’ve got about $200k committed from angels.

Me: Got it. How many meetings have you done so far?

Founder: A LOT!

Me: How many is a lot?

Founder: Oh, maybe about 15-20?

Me: Oh…that’s not a lot. Let’s talk again after you’ve done 200 meetings.

A major problem with fundraising is that it takes up A LOT of time, but if you’re going to fundraise, you have to be dedicated to the process. Too many entrepreneurs half-heartedly fundraise while running their business, and that doesn’t usually work out very well. So how do you know how long you should attempt to raise money before throwing in the towel?

I made up a rule of thumb: 5-100-500. Over 5 weeks, meet with 100 investors to close $500k in your seed round. If you want to close $1m, double all of these numbers.

Why does this rule work?

Disclaimer: I can’t guarantee you’ll be able to close any money, even if you meet with a million investors. On the flip-side, you may be able to close your whole round within 5-10 meetings. This is just a rule of thumb.

Here is why I have this rule of thumb:

1) You need to do enough meetings in order to figure out your pitch and find the right investors.

I’ve talked before about why fundraising takes so long.

For your first 20 meetings or so, you may still be figuring out your pitch. You’ll need to figure out what messaging resonates with investors and what people’s general concerns are. You may feel discouraged after the first 20 meetings, but you should push through and have even more meetings because by then you’ve learned how to pitch your company effectively.

In addition, not every investor you pitch will be in your audience. For example, with my company LaunchBit, an adtech company, we pitched a whole series of VCs who had done adtech deals. It seemed like those people would be a good fit, right? Wrong. What I didn’t realize was that those investors felt over-indexed on ad deals and had been burned by companies that were adtech companies before, and they wanted to get out of investing in ad businesses altogether. Likewise, often investors will do a one-off deal in a space in which they don’t usually invest because they knew some founder really well who offered them a piece of their round. You won’t figure any of this out unless you do a lot of meetings — and you’ll need to do a TON of meetings to then get a decent group of people who are truly interested in your space, thesis, and vision.

So, write to a lot of investors. Get a lot of intros!

2) You need to create urgency by having lots of meetings packed together.

If you are not meeting with enough investors, then you won’t be able to create urgency.

Investors have no reason to come into your round now – even if they really want to – unless there is a chance they cannot invest later at the same price.

Seriously. Think about that. As an investor, it’s in my best interest to wait and get more information if I know I can get in at the same price in 6 months. Right?

As an entrepreneur, you need to create urgency amongst all relevant, potential investors to whom you’re talking. A good way to do this is to pack a lot of meetings together.

Let’s say you do 4 meetings a day for 5 days straight. That means in one week, you can do about 20 meetings. If you did this for 5 weeks, you would easily hit 100 meetings, which is about how long it takes to raise $500k in a pretty fast, efficiently-run fundraising scenario. (Of course, there are always the exceptional baller people who are either in a hot space or have a famous name who can do this in a week, but for the most part, a very fast fundraising situation is about a 1-2 months.)

Packing your meetings together also ensures that all investors are “progressing” at the same time. Ideally you want investors to all be in the same place with their process so that if one commits, the others are able to commit to. So, let’s say you start your fundraising process with VC firm A today and start your process with VC firm B in 4 weeks, and let’s say A commits. B is too early in the process with you to make a decision, and so now B has to decide whether or not to speed up or just decline altogether. But, you need both A and B to be seriously interested in order to negotiate your round. The ideal situation is to start your process with firms A and B around the same time.

What happens if I get to 100 meetings and have not closed my first $500k?

If you cannot close $500k after doing about 100 meetings over the course of about 5 weeks, then it’s probably not worth spending anymore time on this fundraising process.

One of the reasons for having this rule of thumb is to know when to stop fundraising. Sometimes you just need to throw in the towel on fundraising, make more progress, and then go back out and hit the pavement again later. And that’s ok. There’s nothing wrong with that.

The good news is that if you follow this 5-100-500 rule of thumb, then you’ll know the upper bound of time you’ll spend on this process AND you’ll also know that you put in solid effort in trying to make it work.