What questions will early stage VCs ask you?

I thought it might be helpful to create a live running Google Doc of all the major questions that a VC might ask you.

Go to -> Questions that a VC might ask you.

If there are more questions you think I should add to this list, please comment in the Google Doc, and I’ll add additional ones that get multiple votes.

I’ve highlighted in blue the questions that I care the most about. I’ll certainly ask questions about traction just to get an understanding of what has been done in the company, but as a pre-seed investor, we do most of our investments pre-traction. This will, of course, be different for a seed or mango-seed investor.

What is most interesting to me in looking at all the questions I’ve highlighted in blue is that you can see I very much gravitate towards customer acquisition questions.  It isn’t so much that I care about what your LTV and CAC are today.  In fact, in most cases, your CAC will only go up (significantly) and your LTV will hopefully be worth more in the future, so it doesn’t mean anything to me! But I want to understand how you think about getting customers.

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Credit: Giphy

Most entrepreneurs at the pre-seed stage haven’t thought much about customer acquisition. In my view, this is what separates savvy or experienced entrepreneurs from everyone else.

The savviest or most experienced entrepreneurs will often think through the customer acquisition first before even thinking about the product.

At this stage, no one will have all the answers, but a great entrepreneur will think through things like “is this problem important enough that customers will part with their money for this?” and “what is my wedge into this market to beat out alternatives / competitors?”  The savviest or most experienced entrepreneurs will start pre-selling ahead of having a product and know that these results are more telling than surveys.  These are the kinds of things that I want to understand at the pre-seed stage.

What questions do you think should be added to this list?

Some thoughts on balancing family and a startup

One of the more taboo topics in “Startupland” is around having a family while starting a business.  When I was about to have my first child while working on my company LaunchBit, I was catching up with a friend of mine who was also an angel investor in my business.

And then he asked me, “How do you think about balancing your company with a young child?”

Since then, it’s a question I’ve batted around for years.  Is this an appropriate question?  Is it even a good question?  And what is even an answer to this question?

To be clear, my friend didn’t mean any malice by it nor was he trying to use my answer as a piece of information in making a decision about investing — he was already an investor. He was just legitimately curious. But of course, the immediate counter question that comes to mind (and that I articulated out loud) is, “Would you have asked me that question if I were a male founder / CEO?”

We all know that he wouldn’t have.

For as long as I’ve been running my own company — first at LaunchBit and now at Hustle Fund — I have not often engaged in conversations about family in business meetings / business settings.  When other people talk about their kids, I usually just kinda smile and nod.  In contrast, my business partner at Hustle Fund Eric often talks about his family and his minivan.  He shares photos of his children with our investors in our monthly reports regularly.  I don’t think think most of our investors even know that I have children.  There is an unspoken looming fear that many female entrepreneurs with children have — that their abilities and dedication as a professional will be judged and looked down upon because they have children.  This is because there is a notion held by some people in the ecosystem that having a startup while having children puts you at a disadvantage and shows a lack of dedication.  Obviously, not everyone holds this belief, but there is no upside as a woman to sharing that you have children while running a startup.  And so for so long, I’ve just generally kept quiet / private about the whole matter.

And I’m not the only woman to do this.  Countless female founders of mine over the years have asked me for advice and guidance on managing a family while starting a company but have also asked me to keep these questions on the down low or even their plans to start a family on the down low.  I’ve become a confidante of sorts because I’m a female founder with a family in this taboo world.

However, after mulling on this for a few years, I think the exact opposite needs to happen.  Everyone would benefit by sharing advice on tips for handling parenting while running a startup.  And, so I’ve decided to write this post on how I’ve managed to balance parenting while running 2 startups (had kid #1 while running a product startup and had kid #2 while starting a VC fund a couple years ago).  

Before I had kids, I had in my mind an idyllic notion of parenting.  I thought I would swaddle my newborn in cloth diapers, feed breast milk for a year, and follow every other piece of advice from “ideal mother” websites. But then, reality quickly set in – in having my first child while running my adtech company.  The idea of spending an extra 30s putting on a cloth diaper at 2 in the morning in a half dazed stage all of a sudden seemed less exciting — my stance on parenting immediately changed when I became a parent — I just wanted to make sure my kid stayed alive and healthy! 

The reality check

On one hand, there is truth to why running a startup and raising children isn’t easy.  Many people will say that it’s because children take up a lot of time and attention.  Other people say it’s because they increase your financial burden. Both are true but IMO not the biggest issues namely because people are incredibly resilient to constraints — both time and money constraints.

For example, before I had children, I thought I was quite efficient with my time. Post-children, in looking back, I’m actually 3x+ more efficient with time now. I never thought I could eke out so much more efficiency. You can ALWAYS become more efficient with more constraints.

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Playing Bejeweled is something I used to do but don’t anymore…

So, the biggest challenge isn’t additional constraints, because resilient people make things work and make them work better.  I actually think the biggest challenge is that there are just a lot more variables that are out of your control.

For example, your kid gets sick and can’t go to school; that’s out of your control. Your kid wakes up every two hours; you can’t control that either. So how do you deal with last-minute situations? How do you impromptu handle situations you didn’t expect? 

So, here are some key things I’ve learned while leveraging my time as an entrepreneur parent:

  1. You need support. Don’t do it alone.
  2. You need to say no and leverage time.
  3. You need to “let go.” 

Support

It really does take a village to raise children, and I’ve leaned on tons of people for support from the beginning through now. I think people are often afraid to do so, but I think it makes life a lot easier. 

During the first few weeks of motherhood, folks showed up with home cooked food or bought meals / meal gift certificates for me and my husband. Beyond the warmth of love and generosity this brought us, such a little act made a big, practical difference in my day. I could then put my energy towards thinking about my business, focusing on my kid, and even some personal recovery time, instead of worrying about what we were going to eat for dinner. On the flip side, this is probably the easiest, best gift you can get a new parent — meals.

My support network helped me balance time as I became a first and then later second time mom while being an entrepreneur. When my kids were still very young, friends and relatives babysat while I went to networking events, to work, or to sleep when I desperately needed a nap. For example, when I was fundraising for Hustle Fund in 2017, there was a networking event on a Saturday in San Francisco, and my husband was out of town.  For the 2-3 hours that I was there, I left my baby with my friends who lived in the Mission.  As an entrepreneur, at work, you ask for the moon from your business partners and potential clients all the time.  But we don’t often do that with people we’re closest with.  Why not?

My husband holds down the fort a lot, especially when I travel for work or have late meetings or events.  And my parents have spent so much time with my kids when they have no school (and in the very beginning when they couldn’t go to daycare), I can’t imagine accomplishing both startups without them or my extended support network.

Pride is one thing you really can’t afford when launching into the role of a entrepreneur-parent. 

Saying no & leveraging time

As a parent and entrepreneur, I need to leverage my time, and I need as much of my 9am-5pm working block to be free to think / write.

To achieve this, unfortunately, this means I end up saying “no” to a lot and moving things to more efficient channels whenever I can.

For example, people ask other people for coffee meetings a LOT!  Usually without any purpose. I used to do these coffee meetings a lot in my 20s. But, now, I often say “no” to coffee meetings. Critics of this strategy may argue, “Well, I’ve built my best connections through coffee meetings.” And I can agree coffee meetings are great to a) re-build or strengthen rapport with someone you already know / want to catch up with a friend OR b) meet with someone new and build rapport with LOTs of coffee meetings with him/her.  But when I look back, the vast majority of my coffee meetings in my 20s have been one and done, and for those people, that one coffee meeting isn’t enough to end up doing business or hang out socially in most cases.  (there are some exceptions but largely true of the coffee meetings I’ve done over the years) 

Instead, I prefer to stick with email for quick communication and if necessary, move to a phone meeting while commuting. In fact, I set up my Calendly so that bookable times are primarily during my commute at the beginning and end of the day. I end up having a lot of meetings while walking, skateboarding, kick scootering or driving. 

For further “networking”, in lieu of a 1:1 coffee meeting, I like to do group drinks / lunch or hangouts outside of my 9-5 working block.  So if there are a handful of people you want to re-build rapport with or want to get to know, it’s a lot more efficient to group everyone together.  And they’re busy too, so they want to make the most of their limited time too.

This means that when I get to work at 9:00am, I’ve already done a few calls / networking, so most of my 9-5pm day is slated for “thinking work”. I might have a couple of additional meetings during that block where I need to take notes and be fully thoughtful, but I like to have — as much as possible — a whole day to only do thinking and writing work.

The opposite of this schedule is what I had when I was working at Google in my 20s. I had back-to-back meetings all day, and then when I got home, I would, in a tired way, try to think and write. In retrospect, if I were to set up my schedule all over again, I would have skipped many of those meetings, asked people to do most work / coordination over email, and done calls while commuting to free up most of the day.

Exercise

As an aside, exercise is really important to me, and combining work time with exercise (walking, jogging, skateboarding, kick-scootering, etc.) allows me to eke out additional productivity.  I don’t believe in multitasking for most things – I think multitasking makes it challenging to really focus and be present. But I do think that exercise and talking-work goes well together, and this type of multitasking actually is more productive. 

I read Christopher McDougall’s Born to Run (excellent book) and learned that our ancestors used to hunt animals by basically jogging a marathon everyday! Since then, I’ve been trying to increase my miles–some days I walk eight miles–and multitasking with phone meetings helps with this goal, too. I’ve also heard that walking is more conducive to thinking than sitting — but who knows?

In addition, I often use voice-to-type to “write” emails on my phone, especially during commutes. Whether walking, jogging, or scootering with my kids, I can still “talk” to do writing work.

Emails

Lastly, everyone gets TONs of email these days, and email management is a big chunk of work in itself.  It’s really important to me to keep my 9am-5pm working block mostly free — I don’t want to be spending most of that time in email.  With the exception of a few emails that need immediate response, I work on email on the Caltrain on the days that I go up to San Francisco or at night after dinner.

I also recommend SaneBox, Superhuman, and Gmail smart responses to streamline emails and Calendly to streamline calls.

I use SaneBox to filter a lot of emails including subscription emails, emails from people I’ve never met, etc.

I use Superhuman for templated responses so that I can tell everyone the same thing over and over again.  For example, if I need to move a conversation to a call, I send the same templated response with just a couple of keystrokes, and people can pick their own time to chat (during commute hours) through my Calendly calendar management.  I also use Superhuman for offline email processing – so for example, if I’m commuting on the Caltrain to San Francisco, I can plough through all my emails offline quickly.

Re-scope responsibilities and letting go

Outside of work, the time it takes to complete simple chores adds up and eats away time and energy you could be spending either working or with your kids. Since working on a startup means having a budget, my husband and I have re-scoped and re-prioritized our chores to make them as manageable as possible.

Laundry. To save time, we don’t fold laundry. We just don’t. I know – that sounds blasphemous. That’s a tradeoff that we’ve made. We each have a laundry basket to keep clean clothes separate, and we wash each person’s laundry in their own load. I also streamline my clothing options by wearing a @HustleFundVC shirt and jeans almost every weekday. I understand that not everyone wants to keep his/her clothes in a laundry basket or wear the same outfit over and over, but I can tell you that it saves me a lot of time. Sometimes you just have to let go and figure out what is really important to you. 

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Photo credit: Giphy

Food. Each week, my husband and I each cook one simple dish, usually on the weekend. One night, we’ll order cheap delivery, one night we’ll end up eating at someone’s house, and one night we’ll pop a frozen pizza in the oven. Leftovers carry us through the rest of the week. Keeping our meals simple means neither of us has to fret over grocery store runs or recipes.

Dropoff and pickup of kids. We only have one car, so we each take a day to do both dropoffs and pickups.  We are fortunate to have managed to get their schools to be close to our work and home, so our commute, in general, is not that long.  (A miracle in the Bay Area where there is tons of traffic) . 

When my kids are not in the car, this is when I do my car calls so that the drive time is not wasted.  When the kids are in the car, it’s actually a good time to chat with our kids.  Conversations don’t just have to be at home at the dinner table.  They can be in the car too.  Since we only have one car, on other days, I will sometimes combine exercise while the kids are in a double stroller or while we’re kick-scootering together and will take calls when the stroller is empty. 

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Double stroller + skateboard combination day

Contractors. People have often asked me if I have a nanny or if I hire a company to clean our place. I’m not averse to this, and in general, I believe in comparative advantage.  Meaning  — if someone else is way better than you at something, for the right price, you should hire help.  This is how you’d run your business; and, this is how you should run your home.

In our case, both of my kids go to school, so a full-time or even part-time nanny wouldn’t be helpful because he/she would have no children to watch during the day. And by setting up the above the systems, things like laundry actually don’t take more than a few minutes — a chore that could take hours you can shortcut by basically not caring.  So should I pay someone for something that I fundamentally don’t care about is the question? Not sure.

I also make my kids — as young as they are (both under 6) — do chores.  In the beginning, it’s not done well, but at this point, they are actually quite good at cleaning and feeding themselves.

But I do think you should pay for things that you do care a lot about and will take a long time (such as this blog post!). That’s how you can get further leverage on your time.

To summarize

Running a business and being a parent each requires a lot more juggling than without children. But, it also forces you to be pretty dam* efficient that you could possibly imagine.  

To summarize, the biggest way to leverage time with a low budget is to a) ask for help from your community (family, friends, and even your own kids); b) prioritize thinking work and figure out how to get rid of everything else; combine with exercise, and c) reduce how much you care about daily chores. 

My business partner Eric at Hustle Fund is appalled by the fact that I don’t fold my clothes, so these exact strategies are not for everyone, but I do think with some creative juggling, you can eke out a lot of additional efficiencies to make parenting and entrepreneurship work without going crazy. 

Special thanks to my editor Caitlin for pulling the first draft of this together.  Also, the stock photo above isn’t a photo of my kids, but they are cute. 

When is the right time to approach a VC?

My friend Brian Wang posted an interesting topic on Twitter recently — when should you raise money?

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Like everything else, we hear conflicting advice on when is the best time to start meeting with VCs. Some VCs say that you should start building relationships early. Others say that you should only pitch when you are at the right point in your business. What’s a founder to do?

A few thoughts on this:

1) Founders are not treated equally

I’m just going to go ahead and call out this inequality — there are a lot of VCs who are looking to fund people with a particular background. Such as founders who are based in the Bay Area, who come from product or engineering backgrounds, and did really well at a great tech company like Google or Facebook (or now Uber / Pinterest / AirBnB et al), went to a particular school, and perhaps, is of a certain demographic in terms of gender and race. For these founders, a lot (not all) VCs want to start building relationships early so that when these founders hit upon a great idea, they can swoop in and fund the deal.

If you fall into this category, I would definitely meet with many VCs early and start building relationships and then continuing those relationships with the people you like. “Hey, I’m testing ideas in the area of problem X, and I would love to get to know you and see if this is a general area of interest.” VCs will give you lots of time of day if you fit this profile.

If you do not fall into this category — and most of us do not –unfortunately, VCs will really only give you one shot on goal to get your pitch right, and so timing is everything.

(Note: I’m not saying this inequality is right — it’s definitely not. But, this is the state of affairs and I think it’s important to just address that plainly and openly.)

2) Know which VCs fund which stage

If you are in the latter category, it will be really important to do your research on which VCs are funding which stage (as well as obviously verticals / geography / etc). If you are in the post-seed / mango seed stage, then you should pitch investors who fund this stage. We at Hustle Fund, for example, would not be a good fit. (We do pre-seed.)

Seed is a huge range these days — know where in seed you are and where investors are investing and target your pitch to that stage of investor.

3) Get the timing right

Within each stage, it’s important to get the timing of your pitch right. At a high level, all VCs want to invest in startups that:

  • Have a strong direction
  • Have positive momentum
  • Have a clear set of milestones for funding

It’s important to have all 3 of these components.

A) Strong direction

VCs want to see a strong direction. It shows leadership and a goal. Now, you might be thinking, who doesn’t have a goal? Who doesn’t have a direction? There are lots of reasons a startup may not have a strong direction at a given time. For example, if you are still deciding what to build. Or if you are mid-pivot — i.e. you were working on one thing before but are exploring a new thing, that’s not a good time to raise. It’s ok to be in either of these situations, but these are not good times to be meeting with VCs.

If you pivot, you need to test quickly and have conviction to go all in. This is especially hard, because usually when people pivot they already have some momentum on something else, so it’s hard to want to abandon that past work completely in order to take the chance in going after a better opportunity.

Strong direction also means having a plan. You need to do A, B, and C. This is hard in running a startup, because it’s never really clear what you should do. It’s your job to find that clarity and run with it.

B) Positive momentum

Obviously, you want to have positive momentum as well. So, meeting VCs when you are on upward trajectory — e.g. posted your best traction-month ever. Or received a lot of press recently. Or made some key hires. Or onboarded a marquee customer brand. Or are shipping quickly. All of these things are times of positive momentum and good times to be meeting with investors.

On the flip side, if your revenue is decreasing / flatlined, or your unit economics are getting worse or you are getting bad reviews, these are all bad times to raise.

You also need to be having *significant* momentum. For example if you are surveying customers and then you start designing mockups for a prototype, that would be momentum but not significant.

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Courtesy of Giphy

C) Clear milestones

The founders I speak with often don’t have a clear set of milestones when they raise. I often hear founders say they are raising X for 18 months of runway. Investors aren’t interested in funding runway. They want to know what you will achieve or are hoping to achieve with this amount of money. Obviously you may end up missing the mark — and that’s ok, but at least have a clear plan of what you are going after with this amount of money.

You’ll want to paint a story around, “I am raising X because I will use the money to do A, B, and C.”

Applying this to pre-seed, seed, and post-seed stages

Let’s apply all of this more concretely to the various stages of seed.

The three stages of seed these days is roughly: pre-seed, seed, and post-seed.

A) Pre-seed

For pre-seed, you need to have a clear direction and understanding of the problem you are solving. You need to have built a product at a minimum in many cases and in some cases, done some level of customer validation — ideally with real users or revenue traction.  (If you are in a regulated industry such as health / fintech or are building hardware, this is less applicable but you still need to show that you’ve done something rather than just thought up the idea yesterday)

If you are still surveying people or doing customer discovery, you are probably too early to be meeting with investors. Momentum — you need to be shipping fast and getting new customers or leads each week. You should really feel like the ball is moving fast at this stage. I’ll give you an example of what fast looks like at this stage — I chatted with a startup founder in November of last year. They were working on an idea I didn’t find interesting, but the founders seemed impressive. I was very candid and said that I didn’t have conviction on the problem they were working on but if they ended up pivoting, I wanted to take a look at the new idea. The team ended up pivoting in the next month — going all in on their new idea and built the product quickly, and by end of January, they had gotten 2000+ users already. That is what speed to pivot and momentum looks like — new idea, new product, and thousands of users within 2 months. I invested.

B) Seed

For seed, you definitely need to have direction and momentum already. At this stage, investors are typically looking for 30%+ MoM growth (the numbers are small so sometimes even higher). And at this stage, you are starting to form a growth story. This is still a scrappy stage, but you should be focused on painting a picture around how a business is built around your product. Milestones: Based on whatever unit economics you have, can you paint a picture around how you can put money into certain customer acquisition channels and get customers profitably? I would try to get this answer before you meet with investors — even if it’s on a small scale, you need to show the path to how this becomes a big business assuming the channels continue to work (which they won’t).

C) Post-seed

Definitely, by this point, you should be able to articulate what your current unit economics are and in which channels you acquire users / customers and show how if you take X in investment, you can pour it into those channels and turn it into a $2-$3m net revenue runrate business, which are roughly typical series A metrics for a software company. If you don’t have that level of conviction or knowledge on how to do that, then you need to figure that out before you pitch.

Unit economics also matter a lot on customer acquisition spend — if you are wildly unprofitable, you need to figure out how to get closer to the break even point in acquisition. Maybe you need to upsell more to make your customers more valuable. You don’t need to be profitable, but you need have a clear story to growth and profitability before you meet with VCs.

Caveats

As alluded to above, if you are in a regulated area (fintech / health) OR are in hardware / non-software OR ad-based revenue models, then your milestones will be different. But, at a high level, this is still how I would think about whether you have a good raise story before you meet with investors.

After all, unfortunately, most entrepreneurs only get one shot on goal.

How to think about different types of funding for your early stage startup

One of the things that I’m noticing is that the early stage financing scene is changing quite rapidly. It may not feel like it — it’s still hard to raise money of any form, but there are a lot more options now than say even 5 years ago.

Traditionally, you have a lot of tech startups flocking to venture capital firms to raise money, because VCs have done a great job, as an industry, in marketing themselves. But the vast majority of startups who seek VC funding are not the right profile for that type of funding. As an entrepreneur, this is something I didn’t understand — what types of funders are out there and who is a good fit for what?

For example, angels and VCs are often lumped together in the same category. Afterall, they both invest in early stage startups on an equity-basis (this includes investing in convertible notes and convertible securities as well)  But they could not be more different. (See my post on closing angel investors)

In this post, I want to talk about different categories of funding beyond equity-based financing. These are categories I’d not even thought about as a founder. Here are the rough categories of financing options for early stage founders:

1) Equity financing (priced / notes / convertible securities)
2) Revenue based financing
3) Debt financing

…and some permutation of the above!

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Image credit: Giphy

1) Equity financing

This is the one that everyone knows about or at least has heard about. In its simplest form, with equity financing, you as the founder sell shares in your company for cash.

Variations on this include using convertible notes and convertible securities (SAFEs / KISS doc). (see here for details on the differences)

What most people don’t realize is that this is the most expensive form of financing if you are successful. Why? Because your payback amount is delayed significantly and the amount you end up paying back is a LOT if you are successful.

Let’s say you sell 5% of your company for $100k. You think “whee! I have $100k to work with.” In 10 years, if you do incredibly well, and now your company is worth $100m and you sell your startup for an all-cash deal, you pay your investor $5m (assuming no dilution in this example). That is a 50x return for your investor.

Now let’s suppose you had a crystal ball and you knew this outcome would definitely happen.  Knowing that, would you take this deal? Of course not. $5m is a ridiculous amount to give up for a $100k investment. If you knew for certain that this outcome would happen, you would likely try to fund your business with other money so that you could retain the extra $5m for yourself. Right?

Now of course, the reason entrepreneurs take this deal is that you don’t know ahead of time if you will be successful in 10 years! And most founders don’t get to this outcome. A common phenomenon that I see successful founders face is that they are at first incredibly excited to raise their first couple of rounds of equity but then later, they become a bit frustrated that they have taken too much dilution.

Guess what — equity investors need to take a lot of your company in order to justify the risk they take so early on in your business. The heavy amount of equity you sell in your business needs to offset all the losers in a given investor’s portfolio (plus more).

People don’t realize that equity financing is one of the most expensive forms of financing — because you don’t feel it until years later.

The flip side is if you raise equity financing and your company does go belly up, you don’t owe anyone anything. The investor is taking all the risk here as well.

2) Revenue based financing

Revenue based financing is a bit akin of income-shared agreements (ISAs) for individuals. With revenue based financing models, an investor invests money not for shares in your company but for a repayment percentage until you hit a certain cap.

In this model, say we invest $100k and the deal is to pay 10% of your revenue every week until you hit 1.2x or $120k in total repayments. Let’s say that next week, you generate $10k in revenue, so in this model, you pay back $1000 that week. And the week after that, let’s say it’s a great week, and you generate $20k in revenue, so you pay back $2000 that week. Now let’s say that the following week, you have a bad week, and you make $0. You pay back $0. In this model, the investor is with you through the highs and the lows — always taking 10% no matter what. If it takes you 6 months to hit $120k in repayments, that’s a great fast return for the investor, and if it takes you 3 years to repay back $120k, that’s probably a lot slower than the investor would have liked with a much lower IRR. He/she is with you through the ups and the downs — that is the risk that he/she takes.

Investors in this model make money by essentially picking companies that are generating fairly consistent revenue that have low default risk, and they are trying to target quick payback periods so that their IRR is high.

Now, let’s compare this form of investing vs equity investing. Suppose again we are pretty certain we can sell our company for $100m in 10 years, I would rather take $100k in revenue-based financing. Afterall, I would only have to pay back $120k instead of $5m.

But, let’s say we are at the very very beginning of our startup, and we don’t have many customers and not a lot of revenue. Equity financing allows us to keep all of the cash we make to pour back into the business. We don’t have to pay anyone out each week, and that extra cash can help us get to the $100m outcome faster on an equity investing model. Moreover, we probably wouldn’t qualify for revenue-based financing at that stage.

3) Debt financing

The last form of common early stage financing is debt financing. Unlike revenue-based financing, this is time based. This is also the cheapest form of capital but also the riskiest to the entrepreneur. In debt financing, if an investor puts $100k into your company, he/she is looking to be repaid back with interest by a certain date. So, say we do a debt investment of $100k into a company, we might ask for $120k back after 1 year (the principle plus 20% annual interest).

In addition, often, you have to personally guarantee a loan if your company cannot pay it back. Sometimes, debt financing come with warrants as well — if an entrepreneur cannot pay back the debt within a certain time period, the entrepreneur must give up other things including equity in the business.

So even though this is the cheapest form of financing, it’s also the highest risk for the entrepreneur.

Tying this all together…

Let’s analyze all of these forms of financing. First off, usually debt is the cheapest form of capital and equity is the most expensive. Now you might think, “Wait, a minute! 20% annual interest in this last example feels really expensive!” But when you compare the interest to the revenue based financing model and the equity model, it’s not.

To compare all 3 of these financing options, we need to look at the returns on the same time scale.

  • An equity investment of $100k that turns into $5m 10 years later has an average annual IRR of 48% per year.

 

  • A revenue-based financing investment of $100k that turns into $120k in 6 months has an average annual IRR of 44% per year.

 

  • And of course, a debt investment of $100k with 20% interest after 1 year has an average annual IRR of 20% per year.

Of course, if the time scale for the revenue based financing model changes, that will impact the IRR. And if the company that raised money on an equity basis exits earlier or later, that will also change the IRR for the equity-based investment.

Now of course, we are just looking strictly at what capital each scenario can provide. However, it’s possible that with a value-add investor, he/she can change the trajectory of your company. In the equity example, what if it were your $100k investor who introduced you to your would-be acquirer? Then the $5m repayment seems totally worth it. Or what if he/she introduced you to your key hire that led to the acquisition? Totally worth it.

Wrapping this up…

Even though it’s a much cheaper form of financing, founders are typically averse to debt. It’s a natural reaction, because in our personal lives, we go around saying, “Oooooh, debt is bad.” In our personal lives, debt is often bad, because your own cashflows are generally not growing faster than your interest rate. You typically are not getting 20%+ year over year raises each year.

In a startup, if your revenues are growing 20% MoM and your interest rate is only 20% year over year, you are growing your business significantly faster than your debt. And so not only will you have the cash flows to cover this 1.2x multiple of investment, but cash that you can put to use today will make your company worth (1.2^12) 9x more valuable a year from now, while you are only required to pay back 1.2x of the cash you took in.

In the early days when you have no revenue (and maybe you cannot get other forms of financing), equity financing is the least risky for you as the entrepreneur, because not only are you NOT on the hook for losses, but you can pour all revenue back into your business. But once you start to get some certainty around your revenues and some predictability around your cash flows, it may make sense to look at a blend of different forms of financing.

For example, let’s say we’ve started a business, and we are doing $12k per month in revenue and growing on average 20% MoM. What if we did $90k in equity financing and 10% in revenue based financing? If our revenue and cash flows are growing at more than 20% year over year, then this could makes total sense.

On the surface, it may seem insignificant to only raise $10k in revenue based financing, but when you think about what that could potentially become in 10 years,  using the example above, it would be $500k in liquidity in 10 years on a $100m company exit, which is pretty significant.

I think that once you have some level of understanding of your cash flows, it makes sense to look at your composition of financing and try to figure out what proportions of various forms of financing make sense based on your risk tolerance and predictability of your cash flows. I don’t think we do this enough as business owners.

How to close angel investors

Last week I spoke at the LAUNCH Festival Sydney in Australia. Huge thanks to the entire LAUNCH team for bringing me down and for their fantastic event / hospitality; it was an awesome experience and I had a great time!

talk_sydney

Photo courtesy of someone on Twitter – apologies, I didn’t write down who took this — thank you! (Email me and will credit you)

Most of my posts are about raising money from Silicon Valley VCs. But, the world is filled with all kinds of investors. And most businesses are not backable by most Silicon Valley VCs because:

  • They are not software-enabled ideas
  • They are not deemed to be in a large enough market for a VC to invest
  • The founders don’t want to build a “Go big or go home” business
  • Etc…

But these are not bad things. There are going to be plenty of big winners in say e-commerce / direct-to-consumer products that VCs will not back. Or in real estate. Or all kinds of other things. And it isn’t a bad thing if a founder wants to build a business that gets to say $10m per year and sells for $40m. That’s a fantastic outcome for founders. But, most VCs will not back any of these things.

So who do you pitch for money?

The good news is that the world is filled with money. It may not seem like it, but it really is. Your job as an entrepreneur is to find it and unlock it. So, I wanted to share some new material I created for the LAUNCH event on how to find angel and close investors. Here are my slides:

The overall takeaway from these slides is:

  • There are lots of rich people worldwide — they don’t even have to be super rich. There are lots of angels who can write you a $1k-$10k check.
  • Angels may not know they are angels. It’s your job to plant the seed in their heads that you are open to an investment from them!
  • Angels are motivated by many different things; figure out how to tie your story to something that they want; getting an investment – much like sales – is about solving for their needs not yours
  • It’s a numbers game — pitch many many people and don’t give up

Go out and pitch your eye doctor!

Thoughts on our 10 year wedding anniversary

Today is my 10 year wedding anniversary! Happy anniversary to my better half who goes by online alias John Jacob Jingleheimer Schmidt (JJJS)!

wedding

Photo credit: Earl Solis 

Something I’m thinking about today is that I feel so lucky. Namely, I’m glad that someone is willing to deal with me! Being together with an entrepreneur is really really difficult as many of you know. We started dating when I was 23 years old, and like for so many people, at 23, you just don’t quite know where you’re going in life. Years later, my career has taken both of us on a path of so many meanderings, ups and downs, and geographical relocations, and I’m so grateful that JJJS has been through it all with me. A few thoughts and anecdotes to share about all this:

10 years ago

When we got married 10 years ago, I had left my cushy job at Google just months before to become an entrepreneur. I had no idea what I was doing. And, I didn’t know how to make money. At that time, he was starting his post-doc.

On just a post-doc salary, we scrimped and saved like crazy. To make extra money, I did really bizarre side gigs. For example, one of those side gigs was a research study, where some lady from Xerox Parc followed me around for several days. She followed me to the grocery store — and even around in our apartment — literally everywhere and listened in on all conversations and took lots of notes! Other side gigs that I undertook included critiquing resumes for aspiring MBA students in Taiwan and categorizing whiskeys. Looking back, financially speaking, it was an incredibly stressful start, because I was making no money from my startup and the supplemental gigs came in weird ways. (This was before the rise of the gig economy.)

Career sacrifices

Lesser talked about amongst dual income households, in general, are all the sacrifices that are made in order for both people to work — specifically when you have children. When I was 23 with big aspirations, I didn’t think about rearing my future children. Questions like “Who is going to take care of them when I’m traveling?” Or “Who is going to do drop off and pick up?” never crossed my mind. A few years ago, when we had our first child, all of those questions suddenly came up. By complete luck, I picked the right partner, and all of those logistics have worked themselves out, because JJJS has made so many sacrifices to make our household functional. But this is not something that I had thought about at all when we first met.

When I was going through the acquisition process with my startup a few years ago, my baby was just a few months old. As so many of you know, being a parent to a very young child is incredibly draining — babies don’t sleep through the night and they constantly need to feed. So while I was traveling all around the country for meetings about my company, JJJS was holding down the fort at home, slogging through traffic to do all the drop offs and pickups at daycare, not sleeping and being the 24-7 solo parent. At that time, so many people commended me — “Wow, that is badass — YOU are running around doing all these business meetings and pumping in between meetings?  That’s amazing!” But, it’s often the spouse who has to hold down the fort outside of the company who is the unsung hero — for anyone who has ever had young children, wrangling your child is often even more challenging than running a company! (no joke…)

The article that I often refer to and think of that really hits close to home is this one by Andrew Moravcsik where he talks about the necessity of becoming a primary parent once his wife Anne Marie Slaughter’s career became really demanding.

JJJS has made a ton of sacrifices in his own career for mine even though he has big aspirations himself. For example, he left a unicorn synthetic biology startup with great culture and where he was employee #2 to trek across the country so that I could advance my own startup. He is the rock in our family who has taken on much more stable jobs throughout the years to pay the bills, while I’ve largely gone about taking on a lot of risk in building my startup(s) and now nascent VC practice. I know that so much of my own career is only possible because of all his support and sacrifices.

So here we are — 10 years in. Although I could not have predicted what life would look like when we got married, I’m incredibly grateful to JJJS for this journey we’ve been on. I love you, JJJS!