Tremendous

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Why I Passed: “PaintBetter”

May 31, 2024

They were raising $1.7 million at a $20 million cap SAFE. I passed. Here’s why…

“PaintBetter” is an app that teaches you how to paint. ***”PaintBetter” is a composite, not a real startup, and the name is made up.*** But it illustrates why even some startups with really cool products don’t get funded.

The Good

“PaintBetter” had a great app and the founders were very experienced painters themselves. They showed us some of the pictures users had made, and they were really pretty!

“PaintBetter” charged $40/mo for their product and had thousands of users. I love the consumer SaaS business model — it’s produced some amazing outcomes like Duolingo, with an $8 billion market cap.

But as cool as their product was, “PaintBetter” had some real issues…

The Bad

Of their nine full time employees, only two were technical. They were heavily staffed with expert painters, but light on people who could build software.

The lack of tech talent led to a lack of product velocity. It took them years to move from web only to a mobile app, despite the popularity of mobile.

That lack of product velocity showed in their revenue, which was flatlining. Annual recurring revenue (ARR) had grown just 2% a month over the last year.

At this rate, they’d never get to the $100 million they need to become a unicorn.

The founders didn’t have a good strategy to increase growth either. They were focused on adding more classes, but didn’t seem to know how to find users.

Decision Time

“PaintBetter” had a really cool app and some very talented people behind it. But the slow growth, thin technical team, and lack of a growth strategy were dealbreakers for me.

I passed.

To have any hope of making money on this angel investing thing, I need to find companies that are growing like crazy. I’m talking growth that’s ridiculous and unnatural: 3x, 5x, or even 10x a year.

That’s what a best in class startup looks like. And even in those, we’ll lose our money most of the time!

That’s how hard investing in startups really is.

Wrap-Up

I really liked the “PaintBetter” guys, but the deal just didn’t work for me. I hope they prove me wrong and grow like crazy!

And if they do, I’ll show up hat in hand, begging to invest.

Would you have invested in “PaintBetter”? Why or why not?

Leave a comment and let us know! Have a great weekend everybody!

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Why I Passed: ReadMate

The Startup Conveyor Belt

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The Startup Conveyor Belt

May 30, 2024

I invest in companies with $200k to $500k ARR. So why am I meeting startups that just launched?

I think of investing as a conveyor belt.

Each day, I put a few more startups on it. In time, they’ll be ready for checkout!

Shopping at the Startup Store

I try to meet as many software companies as I can that meet these criteria:

1) Launched product.
2) A couple paying customers.
3) Incorporated as a DE C Corp

There are more pre-launch, pre-revenue companies than I have time to meet. But when I narrow it down just a bit, the number becomes pretty manageable!

The third criterion might seem wonky, but it’s really important. DE C Corps can do the things a startup needs to do: issue different share classes, options, etc.

Companies that meet all three criteria are real businesses. That’s who I want to meet.

If I like them, they’ll go on the conveyor belt.

The Meeting

When I meet a company, the first thing I want to know is the founder’s vision. I need to understand that 100%.

I also want to get an idea of where the company is today.

How much revenue do they have? Do they have a lead investor yet?

I gather the basics in about 30 minutes. If it looks promising, I make a note to follow up with them later.

Now, they’re on the conveyor belt…

Watching Startups Grow

Depending on how close the company is to my sweet spot, I will follow up with them in one, three, or six months.

I make a note and when that day rolls around, I shoot the founder a quick message.

As I watch companies grow, I learn a lot about the founder.

How does he handle setbacks? Does he seize opportunities?

After a few months, I know a lot more than I did from that first meeting alone.

Time for Checkout

I met an awesome startup last October at a demo day. I knew right away that I had to invest in it.

I messaged the founder several times in the following months. Rounds take a little longer to come together these days, but I kept hanging around.

Come the spring, it was time to check out! They’d found a lead and grown revenue rapidly in the mean time.

I got my wire in and thanked my lucky stars that I was able to invest! I’ll announce the company soon.

Wrap-Up

I used to try to meet great companies at the perfect time. Now, I just try to meet great companies.

Finding great startups is hard enough. Finding them at the perfect time takes a hard problem and makes it darn near impossible!

With the startup conveyor belt approach, my cart is always stocked with great deals.

Right now, I have a good idea what my next 3 deals will be. And I’ve got some bangers coming.

If you’re investing, try following startups over time. And if you’re a founder, keep in touch with investors you meet, even if you haven’t hit their sweet spot yet!

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What Investors Ask Founders

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What Investors Ask Founders

May 29, 2024

You’re about to meet an investor. What will he ask you? How do you prepare? Here’s what I ask…

1) Vision. The first thing I want to know is the founder’s vision for the company.

My #1 goal in a meeting is to understand the vision. If I don’t understand the scale of the opportunity before me, how can I make a good decision?

You want to be able to state the vision for your company in one clear sentence. Use this as a template: “The vision for Uber is to get anyone a ride anywhere, any time.”

I recently wrote a detailed post on how to nail the vision for your company, which you can find here.

2) What made you start this company? I want to see how much the founder cares about the problem.

To stick it out for 10 years and build this into a unicorn, they have to be obsessed with it.

3) Team. I want to know who they have working on this problem, and how they know them.

I love founders who have known each other a long time. They’ve proven they can get along!

I also want to know why this team is the right one for this job. What about their skills or experience makes them perfect?

4) Who writes code for this startup? Sometimes, a startup has technical folks that no longer code themselves. This question is designed to figure out who’s building and who’s managing.

I like to see half the team or more writing code for the startup.

Engineering-heavy teams tend to win. They can rapidly ship new features that customers want.

What I’m trying to avoid is startups that outsource their engineering to a dev shop. It’s expensive and risky.

4) Demo. Nothing beats seeing a product in action.

I’m looking for products that solve real problems. And I want them to be pretty and easy to use.

Aesthetics matter. Customers want to use pretty products, even in B2B!

5) How do you make money? I need to know what their revenue model is. Common revenue models are a SaaS fee or marketplace take rate.

Then, I do a little back of the envelope math….

How many potential customers exist? What are you charging? If I multiply those, I can estimate a market size.

I usually like to see markets well into the billions, preferably $10 billion plus.

6) Do you have a lead? I usually look for a lead investor. Party rounds can work too if there’s enough cash committed and wired.

I ask about this because I don’t want to be the only one investing in a company. I want to be part of a much larger round that can really get the startup to the next level.

Wrap-Up

These questions will vary from investor to investor. But you’ll see variations of them with many angels and VC’s you meet.

Think about each one and how you’ll answer it.

You don’t need a perfect answer. You just need one that’s clear, concise, and honest to where you are now.

What are investors asking you? What do you ask founders?

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Why I Passed: ReadMate

May 28, 2024

They were raising $1 million at a $10 million valuation. I passed. Here’s why.

ReadMate helps kids learn how to read. ReadMate is a composite, not a real startup. But it shows why some consumer startups get funded, and others don’t.

A Wonderful Mission

ReadMate has guided stories that get children reading on their own. They include animated characters and progress in difficulty over time.

When I met the founder, he seemed to really care about children. He struck me as deeply committed and in this business for the right reasons.

ReadMate has a wonderful mission. But unfortunately, this company also had some real problems.

Looking Under the Hood

Growth was stalling, hitting just 2% a month. A great seed stage company is usually growing at least 10% a month.

ReadMate was also struggling to get customers in a cost-effective way.

Its Customer Acquisition Cost (CAC) was $35. This means it took $35 worth of ads to find a paying customer.

ReadMate wasn’t making much money from those customers. An annual subscription was only $50, and fewer than half of customers renewed.

The founder estimated a Lifetime Value (LTV) of a customer at around $90. With CAC at $35, ReadMate was below a 3:1 LTV:CAC ratio.

This is not good, especially for an early stage company. 3:1 is a bare minimum. I like to see 12:1 or better, because I know that ratio will probably get worse over time as the company grows and they saturate ad channels.

Making a Decision

I love investing in companies that are making a better world. That’s one of the reasons I get up in the morning!

But although ReadMate has a wonderful mission, I had doubts about whether they could pull it off.

ReadMate wasn’t catching on. The company was barely growing.

ReadMate needed more customers, but couldn’t get them in a cost-effective way. The rock-bottom price of the product made paid ads hard to afford.

The company was stuck.

Wrap-Up

As much as I loved the product and the founder, I had to pass on ReadMate.

I almost wish I’d invested in it. I really loved the idea!

But we have to be disciplined.

I can’t invest in companies that aren’t performing well, even if I like them. If I do that, I’ll lose all the money I’ve allocated for investing in startups, and I won’t be able to invest in anyone!

I hope ReadMate turns around in the future and I have another shot at it. I’d love to see them succeed.

How do you look at consumer startups? Leave a comment and let us know!

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Why I Passed on a High Growth Startup

Nail the Vision

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Nail the Vision

May 24, 2024

“What’s your vision for this company?” That’s usually the first question I ask founders. Some are incredible at answering it — but others struggle.

Let me show you how to do this like a pro…

One Clear Sentence

You should be able to get the vision for your company down to a single sentence that is very clear. Don’t use jargon or buzzwords.

You may not “democratize” or “supercharge” anything. You may not make anyone “bionic” or even “AI enabled.” And your vision cannot involve anything “in a box.”

I sometimes use this technospeak myself! And I have to watch it.

These terms are vague and meaningless. They don’t say what your vision for the company actually is.

Tell us what you do and where you’re going. Be as concrete and specific as possible.

Taking Uber as an Example

Let’s try an example. Uber is the most successful company of the last vintage, so we’ll go with that.

Travis could tell investors: “The vision for Uber is to get anyone a ride anywhere, any time.”

That’s darned compelling! Immediately, I see the value in Uber.

Everyone needs a ride sometimes!

As an investor, I am imagining the massive market for transportation transformed. I can almost see the dollar signs.

An Example of What to Avoid

What you don’t want to do is give investors a whole paragraph. A vision must be tight and punchy.

You also shouldn’t dig into every single thing you do. We’re going for the overall vision for the business, not a feature list.

Let’s imagine another way Travis could’ve pitched this:

“Well, we got here because I noticed I could never get a taxi in the rain. And did you know they actually have shared rides in Zimbabwe? It’s so cool! I actually did it once. You should really try it. So I had an idea and I talked to my buddy Garrett, and he started working on an MVP. Right now we have black cars, we actually have 12 of them. And later we’re going to add more black cars and even people’s regular cars, but only if they’re nicer and newer. The regulators won’t like it but I think we can win.”

This is not a tight statement of the founder’s vision. This is a brain dump.

There’s some valuable info in there, but it’s too deep into details. Keep it punchy.

Wrap-Up

Once you nail your vision, you’ll do way better pitching investors. You can also use this vision to inspire employees and attract customers.

People want to be a part of something big. Give that to them!

What’s your vision for your startup? Leave a comment and let us know!

There will be no blog on Monday for Memorial Day. Have a great holiday weekend everyone!🇺🇸🍔

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The Simple Way to Angel Invest

The Power of Small Checks
What a Great Startup Looks Like: Fathom.video

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What a Great Startup Looks Like: Fathom.video

May 23, 2024

No one is more over-advised than founders. So rather than tell you how to run your company, let me show you a fantastic early stage startup in action: Fathom.video.

The Problem

For months now, I’ve been struggling with taking notes at my meetings.

I’ve tried tons of different AI notetakers, and I never liked any of them. They captured stuff I didn’t care about, and failed to capture the most important points.

So, I went back to an old school composition book. And as a founder is talking, I’m having to scribble away like it’s 1980.

It really takes me out of the moment. It’s also a lot of work for me.

But yesterday, I found an incredible tool to take this off my hands!

A Thoughtful Solution

It’s called Fathom.video. Fathom is the most incredible AI notetaker I’ve ever seen. (Btw, I’m not an investor.)

These guys have carefully thought through how meeting notes should work.

Fathom records every meeting and generates a full transcript. It also gives by far the best summaries I’ve seen. It really extracts what’s important, as opposed to random bits of data.

With all that info, you never have to worry about missing something important.

Customer Obsession

Fathom is obsessed with customers.

Just minutes after my first meeting w/ Fathom, I got an e-mail from a very nice lady in Customer Success. She asked how my first meeting went and what they could do better.

How often does that happen with any product you use?

I gave them two thumbs up, plus some enhancement ideas. They can use all that customer input to make this tool better and better over time.

You know what really makes this story crazy? I’m a free user!

If a free user gets that level of attention, I can only imagine how pampered the paid users are!

A Clever Distribution Strategy

So why would Fathom give this incredible tool away? Because they’re smart, that’s why.

The individual plans are free. The team plans cost money, but they’re quite reasonable: $20-30/mo.

This is what’s called bottoms-up SaaS. David Sacks invented it at Yammer, which was later acquired by Microsoft.

Here’s how bottoms up SaaS works…

Individuals start using a product like Fathom because it’s awesome. Eventually, it grows virally within the organization.

If Jim is using it and Mary sees how much easier it makes Jim’s life, she’s going to use it too. Pretty soon dozens of people are using the product.

The corporate IT department gets wind of this and realizes they need an enterprise version. So, they pay for a team plan, and they get multiplayer mode and a bunch of other features.

Boom, sale made!

Wrap-Up

Fathom.video shows us how a great startup operates.

They identified a real problem. Then, they came up with a superb solution to that problem.

They love their customers and do everything they possibly can to help them.

And because their tool is free, adoption is easy. Eventually, those free users drive revenue.

Be like Fathom!

Drill down on a problem and solve it better than anyone else. Talk to your customers constantly, and use that info to get better.

If you can do that, you just might make it big!

What do you think of Fathom’s approach? Leave a comment and let us know!

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The Simple Way to Angel Invest

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The Simple Way to Angel Invest

May 22, 2024

Three years in, this angel investing thing is starting to make sense. It’s like the optometrist — what’s better, #1 or #2?

Investing, Optometrist Style

Let’s say I meet 3 companies in a day — Startups 1, 2 and 3.

2 is better than 1. But when I compare 2 and 3, 3 is better.

Tomorrow, I meet three more startups — we’ll call them 4, 5 and 6. Startup 3 is stronger than 4 and 5, but 6 was even better.

Keep doing that for a month or so. If you’re doing a dozen meetings a week, you’ve met fifty companies.

You winnow them with that A/B approach. By the end of the month, you’ve got yourself a heck of a good bet.

What Makes A Better than B?

How do we know which startup is better? Here are some key things I look at:

Solving a big problem. You can’t build giant companies solving small problems.
Builder founders. To create a software company, you need people who know how to build software. If they outsource it, it will slow them down and cost a fortune.
Product quality. How easy is it to use? How pretty is it?
Founder. Is this person obsessed with the problem they’re solving? Are they tenacious?
Traction. Cash is king! I like to see $200-500k ARR growing fast for seed rounds. That said, I love meeting companies early, when they’ve got just a couple of customers. Then I track them over time.

The Exceptions

I usually make about eight to twelve investments a year. That averages out to around one investment every forty days.

But I don’t do this mechanically. Last August, I did three deals in a month, the most ever.

When the great deals are out there, I take them!

Over 3 years investing, I’ve developed a sense of what a great company looks like. When I meet a startup that’s one of the 10 best I’m going to see that year, I usually know it.

The more founders you meet, the more you’ll develop that sense.

Wrap-Up

The longer I invest in startups, the more I realize this isn’t rocket science.

Deciding what’s the best company out of a hundred is hard. But comparing 1 to 2 and 2 to 3, that’s a lot easier.

Do that enough times, and you just might get lucky!

How do you evaluate startups? Leave a comment and let us know?

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The Power of Small Checks

May 21, 2024

Some angels rip $50k, $250k or more into a startup. I never do that. Here’s why…

I want to build a big portfolio of investments. Three years in, I have 29 companies and I’m headed to 100.

I also want to put aside half the cash I have earmarked for angel investments. That money is what’s called “reserves,” and I put it into the very best companies.

A smaller check might not be what a founder hoped for. But the help those angels provide can be worth a lot more than the money.

How It Works

What does that look like in practice?

I invested in a fantastic startup in the fall of 2022. I put $5,000 into their seed round, which is my typical first check.

A year later, they were growing revenue 4x year over year and had reached annual revenue well into the millions.

Yum yum! Time to break out that checkbook.

I put $25,000 into their Series A. And when I see the founder for coffee on Friday, I’ll have a chance to thank him personally for saving me space in the round!

Learning From a Top Angel

Writing small checks is a great way to get started as an angel. Take it from Tom Hulme, whose angel portfolio went 24x and is now a Managing Partner at Google Ventures. He broke it down on a wonderful recent episode of 20VC:

“If your goal is to get into angel investing, one of the things that no one ever says is the amount you invest is almost irrelevant.
If your job is to learn and demonstrate you add value, then just write small $5k checks. I see so many people that never start angel investing because they think they have to invest $200k at a time. It’s crazy.
If you believe you’ve got to learn, you want to start early with small checks and prove you’re valuable and then actually see if you’re any good at it.”

What’s In It for Founders?

Okay Francis, I get why writing a $5k check is good for you. But why should a founder even bother with that?

Time for some real talk: $5k, $25k, or even $50k is not going to move the needle at a company. If you want big bucks, go to the institutions.

If you want helpful and supportive people around you, find some great angels!

I was just chatting with a founder yesterday, and she told me that her angel investors have done way more for her than any of the VC’s on her cap table.

Why is that?

Some VC’s are incredible. But others are like employees at any other big company — they’re bored, checking Instagram, and waiting for 5 o’clock.

Angels pick the founders we love. We invest our own cash, and since we love the company, we enjoy supporting it!

How Angels Can Help

Here’s a concrete example of how an angel can help you.

I invested in the pre-seed of a great SaaS company last year. The founder is doing great, and she’s heading out to raise her seed round.

I sat down with her and went through the pitch and deck A to Z before any outside investors ever saw it. We worked on the deck and her delivery.

When we were finished, that pitch was a heck of a lot better than when it started. She sounded more confident and the deck was clear and specific.

A pitch like that raises more money. Maybe I only gave her $5k, but a better pitch might raise $500k or more.

Wrap-Up

Angels can be tempted to invest too much too fast. We fall in love with a founder and want to give them $250k and take this thing to the moon!

But success in investing requires discipline. That’s why I stick with small checks.

Once the wire is sent, I watch those investor updates closely and try to help with any of the asks I see.

It’s fun — it’s like solving a puzzle!

And in a decade or so, we’ll find out if I’m any good at this whole angel investing thing. 🙂

What do you think of small checks? Leave a comment and let us know!

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Ohalo: Taking Food Costs to 0

May 20, 2024

Over a billion people live on less than 1,500 calories a day. But David Friedberg’s new startup, Ohalo, could change that forever.

Friedberg announced Ohalo’s breakthrough in plant breeding on the latest episode of The All-In Podcast. Ohalo could massively increase crop yields, lower food prices, and help the poor.

Ohalo’s Breakthrough

Like humans, plants have a mother and a father. The child has a random assortment of genes from both parents, just like humans do. (That’s why human siblings don’t all look the same.)

Let’s say the father plant is heat tolerant and the mother is disease resistant. The child might be heat tolerant but not resistant to disease.

What Ohalo has done is use gene editing to make the child inherit all the genes of both parents. So, the child will be both heat tolerant and disease resistant.

A Massive Opportunity

Ohalo’s early results are mindblowing.

The company’s researchers took two potato plants that produced 33g and 9g of potatoes, respectively, and bred them with Ohalo’s technology. The child plant produced a whopping 682g of potatoes!

Keep in mind, these are just the early tests. What if by 2030, that potato plant is yielding 1000g, or 5000?

Potatoes are just Ohalo’s first market. They plan to expand to every crop in the world.

Pin-point control over plant genes could drive food costs toward zero and yields sky high.

Hundreds of millions of people could get the food they need. And farmers could still prosper by selling huge volumes at low prices.

Will Francis Finally Invest in Deep Tech?

I never invest in deep tech. But I’d invest in Ohalo in a second.

This company presents a giant opportunity: solving hunger and dramatically lowering food costs. They’ve made incredible progress toward that goal.

If Ohalo succeeds, it could be worth $100 billion, $1 trillion, who knows?

I love investing in great SaaS companies. But most can’t reach $10 billion, $100 billion, or certainly $1 trillion.

They’re solving important problems, but the problems just aren’t big enough to produce outcomes like that.

If you want the massive returns, you have to solve a massive problem.

What’s more, Friedberg has an incredible track record — he sold his last company to Monsanto for $1 billion.

Deep tech usually isn’t my thing. I don’t know much about science. But I know a huge opportunity, great results and an awesome founder when I see them.

Ohalo will be a tough nut to crack. But if I’m lucky, I might be able to get in through my membership in the All-In Podcast syndicate.

To be continued…

Wrap-Up

When I heard about Ohalo’s breakthrough on All-In last night, I was dumbfounded. The potential of this company is limitless.

I imagine a future where everyone has the food they need. That’s a world I want to live in.

And if I get my beak wet as well, all’s the better!

What do you think of Ohalo? Leave a comment and let us know!

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