Tremendous

Talking Startups on the OpenVC Podcast

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Raising Less

June 14, 2024

I’m seeing a pattern among my most successful investments. They’re raising a lot less money.

How It Works

Here’s how it usually goes:

Company raises a pre-seed or seed. I invest.
Revenue grows very fast.
Company raises $1-4 million once or twice on SAFEs at higher valuations over the next couple years.
Revenue is at around $10 million ARR before Series A.
Series A only raises a couple of million at a valuation of over $100 million.

The raises after pre-seed/seed are tiny, selling just a couple percent of the company each time. That’s a huge change from how it’s been done in the past, when each round would dilute prior shareholders by about 20%.

These subsequent raises are more about bringing on the right people than raising money. A venture firm that can bring in lots of customers gets the chance to invest $1-4 million, but no more.

‘What Do You Mean You’re Profitable?’

Startups are doing this because they don’t need the money. They are running very cash efficient businesses.

One company I’m an investor in actually has more cash in the bank than they ever raised! This means they’ve been net profitable since the founding — unheardof in startupland.

When Vanta got to $10 million ARR before raising a Series A, it shocked our little corner of the world. Now, Vantas are becoming more and more common.

DoNotPay even paid a dividend recently! They were making so much money they gave shareholders over a million dollars.

I’ve never once heard of a startup doing this before DoNotPay. But we may start to see dividends more and more often.

Do you think DoNotPay will be raising tens or hundreds of millions over and over, diluting 15-25% each time? I don’t think so.

They have no use for it.

What’s Driving Cash Efficiency

Startups may have started becoming more cash efficient because of the down market. But now, it’s taken on a life of its own.

AI has made every engineer 50% more productive. And if we’re all on Zoom, why not bring in engineers from Bangalore for $60k instead of $250k in SF?

Compared to the boom in 2021, we have engineers at 25% of the cost who are 50% more productive. That’s a roughly 6x boost in productivity per dollar in just 3 years*.

No wonder companies aren’t raising as much.

What This Means for Investors

Companies raising less spells trouble for the big, late-stage funds. If your business model depends on ripping $100 million or more into companies, and the companies no longer want your money, you’re finished.

Remember, every time founders take VC dollars, they own less of the company. So if they don’t need the cash, founders have a strong incentive to reject it.

My business model fares much better in this climate. My pre-seed and seed investments will suffer less dilution if companies raise less follow-on funding.

My follow-on investments, which usually happen at Series A, may get done at a higher price. But since my first bet isn’t getting diluted as much, this should even out.

If I see companies raising less becoming a durable trend, I may shift my business model. In a world like that, it may make sense to make a bigger first bet and not do any follow-on.

For now, I’m sticking to my existing strategy and watching the market closely.

Wrap-Up

The greatest thing about these cash efficient startups is that the public markets will eat them up.

Public market investors are sick of unprofitable tech. But profitable companies should get a great reception from the markets. They may even be able to go public at lower levels of revenue, perhaps $100-250 million ARR.

For early stage investors, companies raising less is great. We suffer less dilution and these cash efficient startups should have a smoother path to exit.

But for the late stage guys, the best days may be in the rearview.

Are you seeing startups raise less? Leave a comment and let us know!

Have a wonderful weekend, everyone!

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More on tech:

Talking Startups on the OpenVC Podcast

Why I Don’t Pay for Angel Groups

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*Note: Here’s how Claude and I calculated this. Shoutout to Claude for getting this right, when GPT-4o gave an incorrect answer.

Let’s say I have one engineer at $250,000 and another at $60,000. The engineer at $60,000 has 50% higher productivity than the pricier engineer. Both work 2000 hours a year. Is there a way to calculate the per-unit productivity of each person?

Edit
Yes, we can calculate the per-unit productivity of each engineer by considering their annual salary and relative productivity. Let’s solve this problem step by step.
Given:
• Engineer A earns $250,000 per year and works 2000 hours.
• Engineer B earns $60,000 per year, works 2000 hours, and has 50% higher productivity than Engineer A.
Step 1: Calculate the productivity ratio between Engineer B and Engineer A.
Engineer B’s productivity = 1.5 × Engineer A’s productivity
Step 2: Calculate the per-unit productivity for Engineer A.
Engineer A’s per-unit productivity = Engineer A’s productivity / Engineer A’s salary
Let’s assume Engineer A’s productivity is 1 unit per hour.
Engineer A’s per-unit productivity = 1 unit/hour ÷ $250,000/year
Engineer A’s per-unit productivity = 1 unit/hour ÷ $125/hour = 0.008 units per dollar
Step 3: Calculate the per-unit productivity for Engineer B.
Engineer B’s productivity = 1.5 × Engineer A’s productivity = 1.5 units/hour
Engineer B’s per-unit productivity = 1.5 units/hour ÷ $60,000/year
Engineer B’s per-unit productivity = 1.5 units/hour ÷ $30/hour = 0.05 units per dollar
Therefore, Engineer A’s per-unit productivity is 0.008 units per dollar, while Engineer B’s per-unit productivity is 0.05 units per dollar. Engineer B has a higher per-unit productivity, which means the company gets more output per dollar spent on Engineer B’s salary compared to Engineer A.

Copy

Retry

FS
what is the cost disparity then, per unit of productivity? please express it as a ratio.

Edit
To find the cost disparity per unit of productivity, we need to compare the cost per unit of productivity for each engineer. We can express this as a ratio of Engineer A’s cost per unit to Engineer B’s cost per unit.
From the previous calculation:
• Engineer A’s per-unit productivity = 0.008 units per dollar
• Engineer B’s per-unit productivity = 0.05 units per dollar
Step 1: Calculate the cost per unit of productivity for Engineer A.
Engineer A’s cost per unit = 1 ÷ Engineer A’s per-unit productivity
Engineer A’s cost per unit = 1 ÷ 0.008 = $125 per unit
Step 2: Calculate the cost per unit of productivity for Engineer B.
Engineer B’s cost per unit = 1 ÷ Engineer B’s per-unit productivity
Engineer B’s cost per unit = 1 ÷ 0.05 = $20 per unit
Step 3: Express the cost disparity as a ratio of Engineer A’s cost per unit to Engineer B’s cost per unit.
Cost disparity ratio = Engineer A’s cost per unit : Engineer B’s cost per unit
Cost disparity ratio = $125 : $20
Cost disparity ratio = 6.25 : 1
Therefore, the cost disparity per unit of productivity between Engineer A and Engineer B is 6.25 to 1. This means that the company spends 6.25 times more for each unit of productivity from Engineer A compared to Engineer B.

Talking Startups on the OpenVC Podcast

June 13, 2024

What makes a great deck? Where can angels find deals? I dug into all that and more on the very first episode of the OpenVC podcast!

Here are some of my favorite moments…

2:03: How I got into angel investing and finding some early success.

9:43: Helping founders after I invest.

12:35: Where I find deals.

15:44: What makes a great pitch deck.

22:20: Continue as an angel or raise a fund?

28:50: Why I no longer tell founders “Have a great weekend!”

Right before we started recording, I got to talking with Harrison about British food. He lives in London, and I mentioned how much I love scones with clotted cream and jam.

After the episode, he sent me amazing scone mix, clotted cream, and strawberry jam from England! They were absolutely delicious.

Thanks so much to Harrison and OpenVC for having me on the podcast!

What did you like about the episode? What did I get wrong?

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Why I Don’t Pay for Angel Groups

June 12, 2024

I never pay to be in an angel investing group. Here’s why…

I was chatting with a great up-and-coming angel investor this week. “What do you think of these angel groups that charge a membership fee?” she asked.

Some angel groups charge thousands of dollars to join. When I look at these groups (also known as syndicates), I do the same thing I do when I look at a startup.

I compare them to what else is in the market.

And the market is telling me that this isn’t worth paying for.

Setting the Bar

I’m a member of almost 100 syndicates. So far, the one with the best track record and dealflow I’ve seen is Jason Calacanis’.

Joining that group is free. So why would I pay someone else for an inferior product?

I know that sounds kinda harsh. But this is a free market.

I’m not going to pay for A when B is better — and free!

Getting Paid Twice

Never forget, syndicates are already getting paid.

They generally take 20% of any investment gains you make. This is called the “carry.”

Carry aligns incentives perfectly. They only make money if I make money.

That’s more than fair. I have no problem giving someone 20% of an Uber if I get the other 80%.

But paying just to be in a group and see some deals, then also paying carry? That doesn’t work for me.

Great, Free Syndicates to Check Out

Here are my favorite syndicates.

Of the roughly 100 I’m in, these have had the best dealflow. I’ve done deals with all of them. And all are free:

If you join all these, you’ll have access to tons of solid dealflow. And you’re never obligated to invest in anything.

Always do your own research and make your own decision. Don’t rely on a syndicate lead, me, or anyone else for that!

What Is Worth Paying For

One program that is worth paying for is Angel University.

Jason and LAUNCH run it a few times per year. I’ve taken both their 1.0 and 2.0 courses.

I use what I learned in these classes every single day. And it’s very reasonable — just a couple hundred bucks, and it all goes to charity.

Wrap-Up

Some angel groups are more about socializing than anything else.

I enjoy chatting with interesting people, but in the end, I’m here to make investments. And I don’t need to pay thousands of dollars in membership fees to do that.

I’d rather give that money to a startup. 🙂

Would you pay for an angel group? Leave a comment and let us know!

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More on tech:

Why I Passed: “ProductPreview”
“Not Yet”

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“Not Yet”

June 11, 2024

I rarely tell a founder “no.” Instead, I say “not yet.” Here’s why…

When I first started angel investing, I thought I had to give every company a yea or nay. But over time, I realized I don’t.

Most any startup could be a great investment. It’s just a matter of whether it’s met my criteria yet or not.

Keeping Your Options Open

Saying “not yet” preserves optionality…or, as normal people would say, keeps your options open. 🙂

Saying “no” is the end of a conversation. But “not yet” keeps the conversation going.

That’s important, because none of us knows where the next Airbnb is coming from.

“None Of Us Knows What the Future Holds, My Friend”

Everyone thought Brian and Joe’s idea for crashing in spare rooms was stupid. And at first, they struggled to make it work.

What if I’d met them in year one? If I’d said “no,” they might have taken me off their list.

But if I’d said “not yet,” they might message me once Airbnb was starting to work!

And that is exactly what I what a founder to do.

It all comes down to the quote from Paulie Gualtieri in my favorite TV show, The Sopranos. None of us knows what the future holds.

When I Do Say No

I do give a clear “no” to some startups. Those are usually companies that are way outside my investment area.

So biotech would be a “no,” as would a company in an unfamiliar market like Germany or Nigeria.

I might also say “no” to a startup operating in an extremely small market. For example, an app to find firewood just isn’t addressing a large enough market to produce a big outcome.

Wrap-Up

Saying “not yet” keeps a company on the startup conveyor belt. In time, the company that wasn’t quite right might be just perfect.

If you’re investing in startups, try saying “not yet” rather than “no.” You might be surprised how yummy some of those companies look in the future.

Do you say “no,” “not yet,” something else? Leave a comment and let us know!

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Why I Passed: “ProductPreview”

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Why I Passed: “ProductPreview”

June 10, 2024

They were raising $5 million at a $30 million post-money valuation. I loved the founder and the product was innovative, but I had to pass. Here’s why…

“ProductPreview” connects brands with consumers to give feedback on products before their release. ”ProductPreview” is a composite, not a real startup, and the name is made up. But it shows why even companies with great ideas and committed founders may not make good investments.

The Good

“ProductPreview” has a really cool platform that lets brands test products before they release them.

If Acme Coffee is working on a new blend, they could send me some to test out. I brew it up and let Acme know if I like it or if this new blend is a dud.

No business wants bad reviews and product flops. So testing a product in advance makes a ton of sense.

When I met with the founder, I could tell how much she cared about the business. Her dedication was showing results. “ProductPreview” was closing in on $3 million a year in revenue.

The Bad

“ProductPreview” had significant revenue. But unfortunately, it was barely growing.

In the past year, revenue had grown only about 20%. The best companies at this stage are doubling or tripling year over year.

Worse yet, “ProductPreview’s” burn was out of control. The company was burning over $200,000 a month.

It took “ProductPreview” $10 of burn to add $1 of ARR. A great company at this stage would be burning $3 or less to add $1 of ARR (a burn multiple of 3).

The company employed 41 people, a huge number for a company its size.

Decision Time

I really liked this founder and admired her dedication. I also thought the idea had some real potential.

But the combination of minimal growth, excessive headcount and heavy burn were too much for me. I passed.

Wrap-Up

When I have to say no to a founder I really like, it sucks. I wish I could say yes to everyone!

But these investments have to make money. Otherwise, we won’t be able to keep making them.

Then, there would be no venture capital for anybody.

Would you have invested in “ProductPreview”? Leave a comment and let us know!

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More on tech:
Meet My Latest Investment: Melengo

Why I Passed: “DoorTrack”

Why You Need a Technical Co-Founder

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Meet My Latest Investment: Melengo

June 7, 2024

“I need to be in that.” That’s the first thing I thought when I saw Melengo present at a demo day last October.

Well, I just made it happen!

Melengo makes it easy to develop an apparel line, get financing, and get the products made. You can go from a basic sketch to a beautiful piece of clothing in just a few weeks!

Today, people wade through random factories on Alibaba and hope for the best. The process often takes 6+ months.

In my research for this investment, I went on Alibaba myself and looked at hoodies. One called “cotton” in the description turned out to really be a “cotton/polyester” blend. Ahh, the old bait and switch.

Who wouldn’t prefer Melengo to this?

Founder Justin Kwong is approaching a giant market in a really innovative way. His intense focus on the problem and the strength of Melengo’s traction really stood out to me.

Justin’s long term plan is to make the Uber of manufacturing. Making a product should be as easy as getting a ride – and not just for clothing.

An ambitious vision with real traction today – that’s the kind of company I want to back. Check out Melengo and make some awesome products!

Have a great weekend everybody!

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Meet My Latest Investment: Zest

Why You Need a Technical Co-Founder

Why I Passed: “DoorTrack”

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Why You Need a Technical Co-Founder

June 6, 2024

Lately, I’m seeing a ton of startups with no CTO. Instead, they have a team of engineers with minimal equity. This is a mistake. Here’s why…

Incentives Matter

Startups have to ship new features fast. That’s how they make customers happy and beat competitors.

Who do you think will do that better?

A) A great engineer who owns a large slice of the company and stands to make millions if it succeeds.
B) A great engineer working for a salary who makes pretty much the same no matter what happens.

Humans respond to incentives. A big slug of stock that can make you millions or even billions is a powerful incentive.

You want that key engineer working overtime for you. Stock is how you make that happen.

The Limits of Hired Help

“Francis, you don’t get it! My engineering team is amazing!”

I’m sure they are. But what happens if you run out of money?

Those people are gone, and you’re dead in the water. You can’t ship new features or even fix bugs.

A CTO could help you here. You guys could both reduce salaries or cut them to zero temporarily and try to get the business on even footing.

I’ve seen founders keep working even when their bank account is in the hundreds. But the only way someone will do that is for major equity.

Having a CTO makes your startup resilient. Give yourself every advantage you can!

How Much Should a CTO Own?

By now, I’m sure I’ve convinced you that you need a CTO. 🙂 So, how much should he own?

At the early stage, any co-founder should own at least 10% of the company. Anything less than that, and they’re a co-founder more in name than in reality.

Usually, any founder or employee will vest their stock over 4 years. So if your CTO doesn’t work out or doesn’t stick around, you won’t have given away too much.

Giving a CTO lots of equity means less ownership for you. But owning a smaller slice of a bigger pie is the way to go.

Wrap-Up

Building a startup is next to impossible. You need every single advantage you can get.

A great CTO is one of the strongest advantages there is. Don’t be shortsighted — get someone awesome and give them a big chunk of the company.

When you look back on it at the IPO, you’ll realize it was an incredible bargain.

Do you have a CTO? Do you look for a CTO in companies you invest in?

More on tech:

Meet My Latest Investment: Zest

Why I Passed: “DoorTrack”

Save Money on Stuff I Use:

This platform lets me diversify my real estate investments so I’m not too exposed to any one market. I’ve invested since 2018 with great returns.

More on Fundrise in this post.

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Use this link to sign up and you’ll save $15 on your first order.

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I wrote a detailed review of Misfits here.

Why I Passed: “DoorTrack”

June 5, 2024

They were raising $1.5 million on an $8 million post SAFE. They had a cool product and a dedicated founder, but I passed. Here’s why…

“DoorTrack” is a platform for real estate investors. ***”DoorTrack” is a composite, not a real startup, and the name is made up.*** But it shows why solo founders struggle to raise money.

The Good

“DoorTrack” lets investors see all their properties in one place, view the rent rolls, and model scenarios.

If vacancies go from 5% to 10%, what happens to my cashflow? If I refinance Building A, can I afford to buy Building B?

The tool seemed really useful. Sophisticated scenario planning isn’t a part of a lot of property management systems.

When I met with the founder, “Jim,” I could see that he fit the market perfectly.

He was a small landlord himself, with 8 units. He created the tool to help him manage his own business.

I could tell how excited “Jim” was about this problem. That’s awesome, because without that excitement, it’s hard to stick it out for 10 years and make this a unicorn!

The Bad

“DoorTrack” had a great product and a devoted founder. But unfortunately, “Jim” was all alone!

“DoorTrack” was a single person company, something I rarely see. “Jim” had built the entire platform himself, which was super impressive!

But he clearly needed help. “DoorTrack” made you manually input data from your properties, which users won’t want to do.

“Jim” planned to add an import feature. But had he had a co-founder, this could’ve been done long ago.

In this case and a thousand others, being a solo founder put “Jim” at a disadvantage.

“DoorTrack” would need to ship countless updates rapidly in order to make customers happy. They also needed help with marketing and more.

This was definitely not a one-man job.

“DoorTrack” was also an extremely early stage company. Revenue was just beginning to roll in, sitting at a couple hundred bucks a month.

Decision Time

I loved “DoorTrack’s” product and I could tell “Jim” was smart and dedicated.

But there were some significant negatives here. “DoorTrack” was a one man company with just a trickle of revenue.

Looking back on my 30 investments so far, one trend stands out.

When I invested very early with just a trickle of revenue, the results weren’t great. When I waited until they were over $200k ARR, I had much better luck.

The combination of a solo founder and minimal traction were dealbreakers for me. I passed.

Wrap-Up

“DoorTrack” was a pretty good company in a lot of ways! But with every deal I see, I ask myself the same question:

“Is this the best deal I’m going to see in the next month or so?”

If not, it’s a pass.

“DoorTrack” ultimately didn’t make it. I’m not sure what led the company to shut down, but it’s a shame — the product was really cool!

Try to ignore the fact the company didn’t make it. Would you have invested in “DoorTrack” at the time?

More on tech:

Why I Passed: “FallDetector”

Reply to the Updates!

Save Money on Stuff I Use:

This platform lets me diversify my real estate investments so I’m not too exposed to any one market. I’ve invested since 2018 with great returns.

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If you decide to invest in Fundrise, you can use this link to get $100 in free bonus shares!

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I’ve used Misfits for years, and it never disappoints! Every fruit and vegetable is organic, super fresh, and packed with flavor!

I wrote a detailed review of Misfits here.

·

Reply to the Updates!

June 4, 2024

Most investors don’t reply to updates. I think that’s ridiculous. Here’s why I reply to every single one…

It’s the Least You Can Do

Founders are working 80, 90, 100 hours a week. And they’re doing it on our behalf, at least in part.

The least I can do is take 30 seconds to reply to an e-mail! It’s nothing compared to what they and their teams have to do every day.

Here’s what such a message might look like:

“Amazing growth this month Jim! I know you worked hard for this.

Best,

Francis”

It’s that simple. A brief, positive reply is all you need.

So it burns my butt that according to Dan Siroker of Limitless, 90% of investors don’t do it.

Letting Founders Know You Care

Replying to updates also lets the founder know that someone cares! If you’re just sending updates out into the ether, you must wonder, “Has everyone written this company off already? Does anyone give a hoot?”

I do care, and I want them to succeed. A simple reply to a message is one way to show that.

People want to work with people who care about them and appreciate them. I try to be that person.

Being the Hype Man

Some founders use investor update replies to hype up their team.

One amazing founder I invested in last year puts all the replies into the team Slack. This gets everyone amped up!

I bet those cheering crowds of Bulls fans made Michael Jordan jump a little higher. Startups aren’t so different.

There’s nothing wrong with being a cheerleader sometimes. And if it improves a company’s performance even marginally, I benefit too!

Keeping the Lines of Communication Open

When you reply to updates, you are building a relationship with a founder.

That’s valuable in itself. But there’s also a self-interested reason to do it…

You might want to invest again! And if that opportunity arises, who do you think will get the first shot at it: an engaged investor, or an investor the founder never hears from?

I don’t know where the next Uber is coming from. So whether a startup is doing well or struggling, it behooves me to stay in close contact with the founder.

Wrap-Up

Dan Siroker doesn’t get many replies to his updates. Neither do most other founders I speak to.

There’s no excuse for this.

Luckily for me, this is an easy way to differentiate. I may not know everything, but I can reply to a darn e-mail!

If you’re a founder and you’re not getting replies, don’t worry! This is normal, even if it shouldn’t be.

And if you’re an investor, reply to the dang updates! It’s really not that hard. Keep in mind everything the founder is doing for you!

Do you get replies to your updates? Leave a comment and let us know!

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More on tech:

Why I Passed: “FallDetector”

The Power of Small Checks

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