Tag Archives: Small Business

Business, Technology

Where Should Startups Put Their Money Now?

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This is not investment advice.

So, where should we put our money? The collapse of SVB has every startup looking for answers. The key for the future is diversification.

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Here are some ways to mitigate risk:

The 50/50 Split

The natural next move is to put all our money into JP Morgan or another giant bank. That should fix the solvency issue, but it raises others.

Startups often struggle to work with big, old banks. They can be slow moving and unwilling to offer basic products like business credit cards.

So we need more flexibility. But we don’t want to go through another SVB.

How about we split the difference?

We could keep half our money in a Big 4 bank (JPM, Citi, BoA, Wells). The other half can go to a bank that specializes in startups (Mercury, Brex, etc.).

The Bullet Approach

Investor Jason Calacanis proposed an intriguing solution of his own: 1 primary bank and several smaller accounts to hold emergency funds.

Perhaps you use Mercury as your primary bank. Then, you could also have 1 payroll’s worth of money in each of 3 big banks (JPM, Citi and BoA).

Should anything happen to Mercury, you can still make payroll 3 times.

This is a great solution. It keeps most of your money in one place, making it easy to pay vendors and employees.

But it also preserves safety in a crisis.

Zombie Apocalypse Approach

The safest approach is to never exceed the FDIC $250,000 limit at any bank. However, this is not workable.

$250,000 isn’t even a single payroll for many companies. Payroll systems and vendor payments would have to constantly be switched over.

We need bank safety. But we also need to run a business.

Wrap-Up

We’re still working out the best response to SVB. In the end, no approach is without risk.

But any setup that gets us multiple accounts is a huge improvement.

There’s also a big opportunity here. If a startup can make it easy to balance money across banks, they’ll find a lot of customers.

Where will you be keeping your startup’s cash and why?

Leave a comment and let me know!

More on tech:

SVB Fallout

SVB Fails

Venture Funding Down 65%

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Fundrise

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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Business, Technology

Build in a Small Town!

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For decades, if you wanted to build a startup, you had to be in Silicon Valley. But today, the best place might just be Tennessee.

Or Omaha. Or Little Rock.

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In today’s market, building away from the coasts offers some huge advantages:

1) Lower burn. This is critical in today’s tough fundraising market.

When I meet with companies in NYC and SF, they often have massive burn rates. Part of the reason is high cost of living.

If you rent is $2000 or $3000 a month, you have to pay yourself and your team more. But what if you could rent a 1 bedroom for $750?

In Biloxi, MS, you can!

This means your seed funding will last much longer. That gives you precious time to find product-market fit.

2) Exposure to different opportunities.

I recently met with a company in a small town in the Midwest. They’re building SaaS for meatpacking.

No one in New York or SF is going to think of that. After all, we don’t have much of a meatpacking industry!

The middle of the country simply has different industries than the big coastal cities. And they need tech too!

Would you rather sell a unique, valuable tool to meatpackers or try to sell the 10th team collaboration app to an over-SaaSed startup?

3) Global teams. In the past, you had to be in Silicon Valley or New York because that’s where the talent was.

Now, remote work is common. A startup based in Iowa could hire a developer in SF and a product manager in Brazil.

This levels the playing field, big time.

4) Fundraising is on Zoom. Today, I met with founders in Nigeria, Canada, New York and DC.

Many of the investors are still in the Bay Area and New York. But the founders are everywhere.

Even as COVID recedes, fundraising has stayed on Zoom. It’s so efficient, I don’t think we’ll ever go back.

This means that a Kalamazoo startup and a Palo Alto startup are on similar footing. They both pop up as boxes on the VC’s screen!

If you have a great product and lots of happy customers, investors will take you seriously.

Wrap-Up

There are still some advantages to being in a tech center. You can meet investors at in-person events and learn from other founders.

But balanced against the high costs, you’re better off in the heartland.

Where do you think is a better place to build, SF/NYC or a smaller town? Leave a comment and let me know!

More on tech:

Everything You Always Wanted to Know About Venture (But Were Afraid to Ask)

Don’t Go Into Debt to Fund Your Startup

Sequoia Dumps Citizen: Ruthless, or Reasonable?

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Fundrise

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!

Misfits Market

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.

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Business, Technology

I See Negative Gross Margin Businesses

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I recently met with a startup that’s dead broke. They’re convinced that if only they could raise another round, everything will work.

It won’t. Here’s why…

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Some startups are negative gross margin businesses. Think of this as the old cliche, “We lose money on every one, but we make it up in volume.”

Let’s say I’m going to start an Airbnb killer – Frankbnb. If Frankbnb charges $100 a night to stay in the average room, that’d be a great deal!

But how do I get hosts to accept that low price? What if I paid hosts $200 a night and ate the difference?

Everyone would be so happy! Guests and hosts would flock to my platform, and I’m off to the races.

Sounds great, but actually it winds up more like this:

Why doesn’t this work?

Because with a negative gross margin model, you can’t stop losing money. Ever.

Every guest costs you $100 a night. The more guests you sign up, the better you think you’re doing.

But in reality, each one digs you deeper into the hole.

Obviously, the real Airbnb doesn’t do this. It charges guests, then gives a percentage of that to hosts, keeping the rest.

We investors complain about negative gross margin businesses all the time. But we created them.

Easy VC funding meant startups could always raise another round. Growth was all that mattered.

In 2023, reality is hitting unsustainable startups like a ton of bricks. VC’s are laser focused on margins and burn.

Negative gross margin businesses will either adapt rapidly or die.

Look closely at your startup. Do you make money on each new customer?

If not, take a hard look at your business model before it’s too late.

Are you seeing lots of unsustainable growth? Leave a comment and let me know.

There will be no blog on Monday in honor of President’s Day. See you Tuesday.

Have a great weekend everyone!

More on tech:

Dawn of the Dead VC’s

Top VC Firms Have Great Returns…Right?

From Design to Code in Seconds with AI

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Fundrise

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.

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

Misfits Market

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.

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

Business, Technology

VC Funding Down 67% in December

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Tough times in startupland show no signs of ending. Venture funding fell 67% in December from a year earlier, according to a new report by S&P Global:

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The aggregate value of venture capital-backed funding rounds worldwide dropped 66.7% year over year in December 2022 to $19.71 billion, which is around the same level of annual decline seen in November 2022, according to S&P Global Market Intelligence data.

The number of completed rounds fell by 57%.

These grim stats match what I’m seeing in the market every day. Far fewer deals are getting done, and those that are take longer to close.

The weakest companies have left the market.

The $100 million “seed” rounds in crypto startups with no product or customers were everywhere in 2021. Now, those companies have either given up on fundraising or gone out of business.

The good news is that good companies are still getting funded. I’ve been a part of several multimillion dollar seed rounds in recent months.

These companies have annual revenues in the hundreds of thousands, growing fast. They also have a head start in huge markets.

Even for these companies, rounds take months to close and sometimes don’t fill completely.

If your startup doesn’t have rapidly growing revenue, your chances of raising today are slim. Instead, I’d focus on getting more customers first, which will make your fundraise much easier.

If you are fundraising, you want to raise enough to give yourself runway for two years at least. The 18 month standard I used in 2021 just isn’t enough in this bleak environment.

And don’t count on all that “dry powder” saving you. VC funds may be sitting on a lot of cash, but they’re also deploying more slowly.


As for me, I’m investing in about one company a month, same as I always have.

A few great companies are born every year. In venture, our only job is to own a piece of them.

What do you see in markets today? Leave a comment at the bottom and let me know!

More on tech:

They Passed on Apple, Google and Facebook…Here’s Why

How Startups Change Lives

Entrepreneurial ADD: The Startup Killer

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Fundrise

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.

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

Misfits Market

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.

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

Photo: “The-Movement LosAngeles Graffiti Art” by anarchosyn is licensed under CC BY-SA 2.0.

Business, Life, Technology

How Startups Change Lives

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Many founders work incredible hours. So what’s all this for…just to make someone like me money?

Hardly.

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I know startups can change lives because I’ve seen it happen.

My mom lives in a small town in Wisconsin. Getting around without a car is nearly impossible — but she can’t drive.

She was born blind in one eye, making depth perception a mess and driving a nonstarter. The basic things we take for granted — getting groceries, making a doctor’s appointment, or just grabbing coffee at Starbucks — are very difficult for her.

Or were…until Uber and Instacart!

When I was a kid, we often waited over an hour for a taxi home with our groceries. And we did that outside in frigid temperatures, lest we miss the car.

Now, neatly packed bags appear on Mom’s doorstep, like magic.

We stood in deep snow waiting for the bus if we wanted to go anywhere. I think I spent half my childhood saying “Where the heck is this thing?”

Now, an Uber glides up in minutes, taking Mom wherever she likes.

One of my companies got acquired today. It made me think that despite this financial win, we do this job for a lot more than money.

Whether you’re a founder, investor, or startup employee, we want to make something amazing! We want to make a nicer life for other people.

So the next time you’re staring at your computer at 3am, remember this: what you do matters. You’re creating the future, and it’s going to be awesome!

What motivates you? Leave a comment at the bottom and let me know!

More on tech:

They Passed on Apple, Google and Facebook…Here’s Why

Entrepreneurial ADD: The Startup Killer

Have We Reached SaaS-turation?

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Fundrise

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.

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

Misfits Market

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.

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

Photo: Instacart founder Apoorva Mehta Creator: Laura A. Oda 

Business, Technology

Entrepreneurial ADD: The Startup Killer

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Every time I get the monthly update, I’m confused. Did I really invest in this company?

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There’s a disease that will kill a startup faster than anything else. It’s called Entrepreneurial ADD.

This deadly condition involves a founder who gets distracted too easily. Rather than nailing one business model, he’s always running off in new directions.

Hot new trend? He’ll pivot the entire business to work on it.

New product showing signs of working? Trash it and build something even cooler!

Entrepreneurs have boundless enthusiasm and tons of ideas.

This can help them innovate and succeed. Or it can have them running around like chickens with their heads cut off, accomplishing nothing.

Take the example of my portfolio company. After seeing some early signs of success with one product, they pivoted to something completely different.

The founder continued to chase down every hot trend in tech. Meanwhile, revenue shrunk and cash evaporated.

Now, runway is minimal and the chances of raising more money are poor. In this environment, a cash burning company with declining revenue is not investable.

What if they had simply hammered away at their original, successful business? They might be break-even by now and raising from a position of strength, if at all.

Venture capitalist Ben Narasin notes that in decades of investing, he’s almost never seen a pivot work. How many companies pivot over and over and succeed?

Probably almost none.

Don’t abandon a winning business model for the shiny new toy! Double down on what works.

And if your model isn’t working, fix it! If a particular problem is important to you, don’t just abandon it at the first sign of difficulty.

Because guess what? The next business will be difficult too!

Do you struggle with Entrepreneurial ADD? Do some of your founders have it?

Leave a comment at the bottom and let me know!

More on tech:

Have We Reached SaaS-turation?

Is 2023 the Best Time to Invest in Startups?

The Magic of Milestone-Based Funding

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Fundrise

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.

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

Misfits Market

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.

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

Photo: Jack Dorsey, one of the very few CEO’s to successfully pivot a company. He pivoted Odeo to Twitter. “Jack Dorsey” by jdlasica is licensed under CC BY 2.0.

Business, Technology

Is 2023 the Best Time to Invest in Startups?

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It was a rough 2022 in tech — layoffs, shutdowns, and stocks falling off a cliff. But 2023 promises to be a golden age for startup investors.

Here’s why I’m more excited than ever to invest in 2023…

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Valuations

In 2021, you could raise venture capital for a fruit stand.

I saw crypto startups with no product or customers raising “seed rounds” at $100 million valuations every day. Deals moved so fast that if you did any diligence, you might miss it.

Now, the market has slowed to a crawl. The vaporware startups have disappeared.

What’s left? Great companies raising at reasonable prices.

I’m often paying half as much for a company as I did in 2021. Even fast growing startups with several hundred thousand in yearly revenue go for about $10 million.

A lower entry price means more upside. And since a seed investor like me probably won’t exit for 10 years, prices could skyrocket in the mean time.

Focus

Founders today are laser focused. They’re not speaking at conferences or rolling out NFT’s.

They’re fighting to make sure their businesses survive.

Founder distraction is a giant killer of startups. For better or for worse, facing bankruptcy concentrates the mind.

I think founders and teams will perform better under this pressure, difficult as it can be.

Access

These days, I can get into any deal I want. Founders have to cast the net beyond the most famous firms in order to raise a round.

For angels and new VC’s, this is a boon. If you ask to get into any deal out there right now, it will probably happen.

There are only a few companies founded every year that matter. Our only job is to get as big a slice as possible of those deals.

That’s a lot easier to do in 2023 than it was in 2021.

Uber, Airbnb, and Block were all founded during the financial crisis. Someone is out there creating the next Uber right now.

It’s our job to find them.

How do you feel about investing in 2023? Leave a comment at the bottom and let me know!

More on tech:

The Magic of Milestone-Based Funding

Is SBF Laundering Money As We Speak?

Zero to One

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Save Money on Stuff I Use:

Fundrise

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.

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

Misfits Market

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.

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

Photo: Uber founder “Travis Kalanick” by jdlasica is licensed under CC BY 2.0.

Business, Technology

The Magic of Milestone-Based Funding

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There’s a law in Silicon Valley as basic as F = ma: milestone-based funding. It’s why you can’t raise $100 million on day 1. It’s also why my positions in my strongest companies are many times larger than my weakest ones, as if by magic.

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…You show incremental progress. We’re engaged in milestone-based investing where the amount of money you raise and the valuation you’re able to get scales with the amount of proof you have delivered to investors about the company.”

David Sacks, All In Podcast #43

Milestone-based funding means that you don’t get all the money your company will ever need at once. Instead, you get a little now, go accomplish some stuff, and come back for more.

In venture’s early days, a company was financed once, and it either sunk or swam. Milestone based funding lets investors allocate their capital more efficiently.

The most successful companies need more money to grow. Meanwhile, throwing good money after bad rarely gets you anywhere.

Let’s see how this works in practice by looking at two companies in my portfolio.

A Tale of Two Startups

I invested in both Company A and Company B within weeks of each other in the spring of 2021. With high hopes, I sent in my wires and envisioned a wonderful future for both.

Well, I was half right.

Company B has increased revenue 6-fold since then. It’s expanding to new markets and signing up customers like crazy.

For Company A, the picture isn’t nearly as rosy.

Revenue hasn’t grown at all and burn is heavy. Raising more money is impossible and bankruptcy is a very real possibility.

How Milestone-Based Funding Played Out

My initial investment in both these companies was exactly the same amount. But now, my investment in Company B is almost 6 times as large.

The reason is very simple: I doubled down in Company B and did not reinvest in Company A.

Company B recently raised a much larger round at the same price as before. With amazing progress, I was happy to 6x my investment.

Add in a little dilution from this round, and my position in Company B is nearly 6 times bigger than my position in A.

If Company B continues to perform well, I’ll be putting in even more. That, plus increases in valuation, may eventually make my investment in B dozens or hundreds of times larger.

What This Means for Founders

Raise an amount appropriate to where your company is at today.

If you have only a couple of customers, you’re probably looking at around $500,000 in pre-seed. If you have $250,000 ARR, you may be able to raise a $2 million seed round.

Then, keep those investors updated on your progress. Remember, there’s more money where that came from!

Milestone-based funding is a brutal system, but it’s necessary.

I’d love to help Company A with another check. I love what they do and I want to see them succeed.

But I just can’t justify it when other startups are performing better.

What questions do you have about fundraising? Leave a comment at the bottom and let me know!

More on tech:

Is SBF Laundering Money As We Speak?

Zero to One

Why I Just Invested in Rilla, the Killer App for Outside Sales

Note: Shout-out to Fathom.fm for finding that David Sacks quote in seconds. Making audio searchable really is the future! Delighted to be an investor in this great startup.

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Save Money on Stuff I Use:

Fundrise

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.

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

Misfits Market

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.

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

Photo: “David Sacks” by jdlasica is licensed under CC BY 2.0.

Business, Technology

Seedscout: Where Underestimated Founders Win

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Every morning, I have dozens of new LinkedIn messages from founders. I seldom have time to reply. But what if there were a better way for founders and investors to meet?

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Enter my latest investment, Seedscout. Seedscout is an awesome new platform for founders to meet investors.

The magic of Seedscout is that there’s a monthly fee. This filters off people who aren’t serious.

What’s left? Awesome founders I want to meet!

I find myself meeting with almost every Seedscout founder who asks. Meanwhile, my LinkedIn requests languish in digital limbo.

I recently met an amazing founder on Seedscout whose startup is growing revenue at 70% a month. Once I wiped the drool off my chin, I reached for my checkbook!

When a platform gives me deal flow like that, I pay attention to their next intro. Meanwhile, since I rarely find solid deals via cold messages, I often don’t have time to respond to those messages.

For founders without a strong network in venture capital, Seedscout is a super power. You can buy your way in.

With plans starting at $100/month, a scrappy young founder can drive Uber for a few hours and pay for a membership.

Seedscout Founder & CEO Mat Sherman is fanatical about opening up venture capital to all great entrepreneurs. In an industry where just 2% of funding goes to women and just 0.4% to black founders, Seedscout is changing the rules of the game.

In time, Seedscout may replace LinkedIn and AngelList. For me, it already has.

I’m delighted to be an investor in innovative startup. Best of luck to this scrappy team as they take Sand Hill Road by storm!

I’m on vacation for the next two weeks. I’ll see you again on Monday, December 19th!

Until then, please enjoy some classic posts from the archives:

The Startup Pitch Checklist

Mark Twain: Venture Capitalist

North Jersey’s Secret Campground

The Swami Who Taught Me About Politics

The Ultimate Score: Turning $300k into $2.4 Billion on Coinbase

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Save Money on Stuff I Use:

Fundrise

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.

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

Misfits Market

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.

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

Business, Technology

Why I Just Invested in Rilla, the Killer App for Outside Sales

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Every day, sales reps go to meetings across America to land that big deal.

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Their managers hope they absorbed the lessons of training and can bring in the sale. Unfortunately, they rarely have the time to go along.

But with cutting edge AI, sales managers can now analyze every customer meeting without ever leaving their office!

Rilla records sales meetings and tags the most important moments. You’ll know if reps are following the script, what customer objections are, and a lot more.

Other platforms like Gong or Chorus may work for inside sales with its clean audio. But for outside sales in the noisy, chaotic world, Rilla is king.

You just press record on a phone or tablet and that’s it! Rilla takes care of everything else.

No wonder sales teams are adopting Rilla at an incredible rate.

Sales managers see a 20-30x productivity increase. Reps get the feedback to make their pitch better than ever, meaning more commissions.

I’m delighted to be an investor in Rilla’s recent seed round. The founder, Sebastian Jimenez, is tenacious and laser-focused on his customers.

If you’re in outside sales, book a demo with Rilla and see what it can do for you!

More on tech:

Seeing Through SBF: How One VC Found the Truth

Getting to $10 Million ARR Without a Series A

Why I Love B2B Startups

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Save Money on Stuff I Use:

Fundrise

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.

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

Misfits Market

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.

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

Photo: Sebastián Jiménez, Founder & CEO of Rilla