Tag Archives: Silicon Valley

How to Answer Investor Questions

There’s tons of advice out there on how to pitch investors. But what about what comes next?

After any pitch, investors are likely to ask numerous questions. How do you answer them in the most effective way?

Here are some tips:

Pacing

One of the biggest mistakes I see founders make is taking too long to answer a question. The answer should be about the same length as the question.

When you take too long answering one question, you run out of time to address others. You’re also more likely to start rambling and lose the investors’ attention.

Be Direct

Investors may have some tough questions for you.

Tough as they may be, you should answer these questions as directly and specifically as possible. If someone asks for your churn figures, give them numbers, not a story.

Whenever I sense a founder isn’t giving me the information I need to make a decision, I start mentally moving on to the next company.

Don’t Get Defensive

For early stage startups, no one is expecting you to have everything dialed in just right. If you had that, you wouldn’t be a startup.

You’d be a Fortune 500 company!


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So when investors ask the tough questions, don’t feel like we’re attacking you. We’re not.

We just need certain info to make a financial decision.

It’s Okay to Not Know

An investor might ask you for some very specific info in a meeting.

It’s perfectly okay to say you don’t have that information in front of you. What’s important is to promptly follow up and get the investor the information they asked for.

Always Be Honest

Many founders have wanted to put a company logo on a slide when that company isn’t really a customer…yet. Or maybe claim a big name investor is in the round when in reality you’re just talking with her.

Don’t give into these temptations. When you make presentations to investors as part of a fundraise, you’re opening yourself up to serious legal liability.

If you make a knowingly false statement, you could go to prison for securities fraud.

Most founders would never cross this line, but for those who might be tempted, I urge you to protect yourself and just give the truth.

Be Glad for the Grilling!

Answering a ton of questions can be really tough! But be glad for each one.

One of the surest signs I’m not interested in a startup is when I don’t ask any questions. I’ve already ruled the company out.

I often ask questions when I’m wondering if there’s any reason not to invest. And I’m not alone.

Wrap-Up

These investor questions are often the last step before a check.

Keep your answers brief, concise, and factual. When founders crisply answer questions with detailed information, I find it enormously impressive.

Best of luck!

What has it been like for you answering investor questions? What did I miss?

Leave a comment at the bottom and let me know.

Have a great day everyone!

More on tech:

The Startup Pitch Checklist

Growing Veggies on Mars

Startups’ Secret Marketing Weapon: Blogging

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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.

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Misfits Market

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

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Fathom: the Podcast Player from the Future

Let’s say I have a question: “how do angel investors choose startups?” I go to Google and type it in, right? 

But what if the best answer is in a podcast? That audio is trapped somewhere in the dark world of RSS feeds, along with great answers to millions of other questions.

Until now! Fathom makes it easy to search podcasts. 

Let’s try my search on Apple Podcasts:

Bupkus. Now let’s try it on Fathom:

Right away, Fathom directs me to a highly relevant clip from This Week in Startups, a podcast I love! Jason advises me to diversify my investments and make sure I’m choosing companies with products in market.

Sage advice. Question answered.

Do you see how powerful this is? Tons of smart people are talking on podcasts every day, but unlike text, that info is almost impossible to search.

Fathom grew out of a side project during the COVID lockdown. Here’s co-founder Paul Bloch:

Ken, my cofounder reached out to me and mentioned that during the covid lockdown he’d been working on a prototype AI that could answer questions using podcast content. Ken’s a podcast lover and big Lex Fridman Podcast fan. Ken asked if I wanted to help develop the idea and product with him. 

After we started in earnest we felt that there were many more ways we could bring the power of AI to the user and innovate in how people experience podcasts. That’s what brought about the feed of AI-recommended episodes that play AI-generated highlights. 

…I believe in January of 2021 Lex Fridman had an interview where he specifically mentions how game-changing it would be to search inside podcasts. That was the moment of kismet that really made us excited about the potential of the product. Months later we had a prototype, incorporated the company, and had our first investor check. Things started moving fast the moment we really committed to bringing our vision to life.

The application is available on desktop or iOS. As a podcast maniac, I’m really excited to be an investor in this great company!

Give Fathom a try and have fun listening to some awesome episodes! 

More on tech:

Vade: The Future of Parking

Founders’ Biggest Pitch Mistake

Male Contraception With an Ultrasound Device?

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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 and returns have been great so far.

More on Fundrise in this post.

If you decide to invest in Fundrise, you can use this link to get your management fees waived for 90 days

Misfits Market

My wife and I have gotten organic produce shipped to our house by Misfits for over a year. It’s never once disappointed me.

Every fruit and vegetable is super fresh and packed with flavor.

I thought radishes were cold, tasteless little lumps at salad bars until I tried theirs! They’re peppery, colorful and crunchy!

I wrote a detailed review of Misfits here.

Use this link to sign up and you’ll save $10 on your first order. 

The #1 Reason I Say No to Founders

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Every month, I look at over 200 startups. I choose one.

Among those hundreds of companies raising funds, I always see tons of cool ideas. So what distinguishes the companies I choose from all the others?

The number 1 reason I say no to founders is that they’re raising funds too early.

Many of the pitches I see are little more than a few slides with a lot of projections. But most investors want more than projections.

We want a track record.

For companies raising seed funding, I expect at least six months of revenue, growing month over month. For consumer products that are pre revenue, I’d like to see a similar track record of user growth.

Many companies I see trying to raise seed funding are nowhere near that. They have no revenue and often not even a product! 

What founders have to realize is without any track record in the market, how can investors tell if your company is a good bet?

Without a track record, the only thing an investor has to go on is the team. And talented as so many founders are, the fact is that most founders raising seed rounds are unknown.

They might build the next Uber or Airbnb, but they haven’t done it yet. 🙂 

Raising money without a track record in the market is much easier for serial entrepreneurs with a big win behind them. If you sold your last company for $1 billion, I’m willing to fund you a lot earlier.

Founders will make the fundraising process much easier for themselves if they build their company to at least a few thousand a month in revenue before raising a seed round. 

This gives them greater credibility among investors. It shows they know what investors are looking for.

Bootstrapping your company to thousands in monthly revenue isn’t easy. But neither is raising money without a track record to point to.

Another benefit of doing some building before the fundraising is that you’ll have a better idea how to deploy that capital because your business is more mature. A big check from a VC won’t do you much good if you don’t know how to spend it to drive growth.

Best of luck to everyone out there building!

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More on tech: 

Tech Plunge Hits Early Stage Startups

Founders Biggest Pitch Mistake

Why I Just Invested in Deft, the Best Way to Shop Online

Photo: “Startup” by Skley is marked with CC BY-ND 2.0.

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Save Money on Stuff I Use:

Amazon Business American Express Card

You already shop on Amazon. Why not save $100?

If you’re approved for this card, you get a $100 Amazon gift card. You also get up to 5% back on Amazon and Whole Foods purchases, 2% on restaurants/gas stations/cell phone bills, and 1% everywhere else.

Best of all: No fee!

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 and returns have been great so far.

More on Fundrise in this post.

If you decide to invest in Fundrise, you can use this link to get your management fees waived for 90 days

Misfits Market

My wife and I have gotten organic produce shipped to our house by Misfits for over a year. It’s never once disappointed me.

Every fruit and vegetable is super fresh and packed with flavor.

I thought radishes were cold, tasteless little lumps at salad bars until I tried theirs! They’re peppery, colorful and crunchy!

I wrote a detailed review of Misfits here.

Use this link to sign up and you’ll save $10 on your first order. 

What I Look For in Startups

You’ve been meeting with investors day after day. You get a lot of “very interestings” but no actual checks.

What are these people looking for?

Today, I thought I’d explain what I look for in a startup.

As an angel investor, I invest in about 1-2% of the companies I see. Here’s how I choose:

1) Are you solving a big problem? Take Uber: it gets you from anywhere to anywhere, anytime, easily.

Mobility is a huge problem. Any technology that can make it easy to get places has a giant potential market.

What is an example of a company that isn’t solving a big problem? Imagine a better way to search tweets.

That’s a feature, not a product. It’ll probably get copied by Twitter or Twitter will buy it for a small sum.

2) Are you growing revenue 20% month over month? I want to see clear signs that your vision is shared by customers.

Dollars in the door are the best sign there is. I find about 2-3% of seed stage startups are growing this fast.

If the company is pre-revenue, I would also find a similar growth rate in users quite persuasive. But revenue is best.

The greatest companies of today, like YouTube, had incredible growth early on. That’s what I’m looking for.

3) Is the product awesome? If there’s any way for me to use the product, I always do so before investing.

Maybe you have great early growth, but if the product isn’t solid, it may be hard to sustain that pace.

If I can’t use the product (most B2B SaaS, for example), I ask for a detailed demo. I also read every review of the product I can find.

3) Is there good founder/market fit? If you used to work on M&A at Goldman Sachs and you started a company to help people find sustainable clothing, I’m going to have a few questions.

Why would you start a business that is so far removed from your background? Perhaps you have solid reasoning, like a long-term commitment to environmentalism via volunteer work.

Or maybe you’re just in it for the buck. I have nothing against making money, but starting a company is so hard that if the motivations are only pecuniary, you will likely give up.

4) Are you raising at least $1 million? Most companies I invest in are raising $1-3 million seed rounds.

Why does this matter? Companies that raise a seed round of at least $1 million are far more likely to be successful, per a Crunchbase analysis.

A big round means you can hire lots of developers and sales people. That lets you get ahead of your competitors, fast.

When I see companies raising a round of $250-$500k, I often think this isn’t enough to move the needle.


I hope this helps clarify how investors pick startups. Other investors may have different processes, but I think you’ll find a lot of similarities.

Best of luck and happy fundraising!

More on tech:

The Original YouTube Investment Memo

How Startup Founders Turn Investors Off

Why I Just Invested in Gauge, the Best Way to Sell Your Car

Photo: “Historical Documentation Defenestration WHY Sign” by Lynn Friedman is licensed under CC BY-NC-ND 2.0

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Save Money on Stuff I Use:

Amazon Business American Express Card

You already shop on Amazon. Why not save $100?

If you’re approved for this card, you get a $100 Amazon gift card. You also get up to 5% back on Amazon and Whole Foods purchases, 2% on restaurants/gas stations/cell phone bills, and 1% everywhere else.

Best of all: No fee!

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 and returns have been good so far. More on Fundrise in this post.

If you decide to invest in Fundrise, you can use this link to get your management fees waived for 90 days. With their 1% management fee, this could save you $250 on a $100,000 account.

Misfits Market

My wife and I have gotten organic produce shipped to our house by Misfits for over a year. It’s never once disappointed me. Every fruit and vegetable is super fresh and packed with flavor. I thought radishes were cold, tasteless little lumps at salad bars until I tried theirs! They’re peppery, colorful and crunchy! I wrote a detailed review of Misfits here.

Use this link to sign up and you’ll save $10 on your first order. 

Inside a Startup Accelerator Demo Day

Yesterday, I attended the Remote Demo Day for the latest class from the Launch Accelerator, a startup accelerator run by noted investor Jason Calacanis. We hear a lot about accelerators (also known as incubators), from famous programs like Y Combinator or Techstars to small, local outfits.

One thing most of them have in common is a demo day. This occurs at the end of the accelerator program and gives the startups an opportunity to pitch their company to investors.

So what goes on at these demo days?

Seven companies had three minutes each to present. A panel of judges (investors at venture firms) and members of The Syndicate (Calacanis’ investment group) submitted questions. Founders then had two minutes respond. Finally, both the judges and syndicate members voted on their favorites.

Here are some interesting trends I noticed from the meeting:

1) Business-to-business companies got a better reception than business-to-consumer companies. Business customers are less fickle and more likely to remain customers once acquired. They also have deeper pockets, and if you can show them that a technology clearly saves them money or gives them an important new capability, they’re likely to buy. Consumers are harder to pin down.

2) Startups are very diverse now, in terms of race, gender and geography. Two of 7 founders were female, and two were minorities. This isn’t equal representation, but it is progress. The companies came from all over America, from the usual suspects (Bay Area, NYC) to the South and even Europe.

3) It’s not all software companies. My favorite was actually a beverage company. Show investors some substantial recurring revenue and fast growth, and you may find checks flying back at you. What’s more, so many companies these days have a tech angle. This company sells their beverages online in a subscription model.

4) Everyone’s nice. Despite stereotypes of grizzled money guys telling you “It’ll never work!” the reality is that reputation is critical in this industry. Expect specific questions that might be hard to answer, but don’t expect (or tolerate) jerks.

Expect specific questions that might be hard to answer, but don’t expect (or tolerate) jerks. #startups

5) Even early stage companies fresh out of an accelerator have real products and revenues. There were no companies just trying to get an idea funded or still working on a prototype. They wouldn’t have made it into the accelerator in the first place, and even if they had, they wouldn’t have attracted any investor interest. Investors help business scale. They don’t help ideas become products.

So, who got funded? That remains to be seen, but if there’s enough interest from syndicate members, several could potentially get the nod. I know I’m interested in investing in two of the startups I saw.

We are so fortunate to live in a country that produces incredible entrepreneurs with such regularity. This was the 21st class to go through the accelerator, and there will be many more!

Congrats to all the great founders that presented, and a happy weekend to all my readers!

Dig into these posts for more on startups:

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Photo: “Great white shark” by Gussy (Luke) is licensed under CC BY-NC-ND 2.0

How Do You Know If a Startup Is Getting Traction?

Investors look at a lot of startups before laying a bet. But how do we know if the company’s product is catching on, or has failed to find traction? And as a founder, how do you know if you’re headed in the right direction or…nowhere?

In a recent episode of the superb podcast This Week in Startups, investor Jason Calacanis and guests Craig Zingerline and Allen Chen broke down a key metric: customer retention.

Do you have product-market fit? There’s no one better to answer that question than the people who use your product every day. Here are the customer retention numbers to look for, over a 6 month period, for different types of startups:

  • Consumer social (think Instagram): 25% is good, 45% is great
  • Consumer transactional (think Uber): 30% is good, 50% is great
  • Consumer SaaS (think Netflix): 40% is good, 70% is great
  • Small and medium business (SMB) and midmarket SaaS (think Freshbooks): 60% is good, 80% is great
  • Enterprise (big company) SaaS (think Oracle): 70% is good, 90% is great

As you can see, business-to-business products should be a lot stickier than business-to-consumer ones. Consumers are fickle and their investment is minimal. At the other end of the spectrum, major corporations don’t adopt new software lightly. It’s a process that sometimes takes years and costs a fortune. So they don’t switch often, either.

The panel emphasized that you don’t have to get to these numbers right away, but that they should be a goal. Good luck!

For more on startups, check out these posts:

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Photo: “Jason Calacanis” by jdlasica is licensed under CC BY 2.0

“Everybody Thought I Was Crazy”: How Brian Armstrong Built Coinbase

“Everybody thought I was crazy.”

That’s Brian Armstrong, CEO of Coinbase. When he started the company in 2012, it was a small and quirky startup. Bitcoin had only been in use for three years and remained relatively obscure.

But now, it’s safe to say not many people think Armstrong is crazy. His company just went public yesterday and its valuation currently sits at $66 billion. Coinbase holds $200 billion in cryptocurrencies, around 11% of all crypto in existence. So how did Armstrong go from lunatic to visionary?

Armstrong had to build interest in his new product. He settled on a cost effective and attention getting marketing tool: send people free money. But not just any money; bitcoin, of course! He sent tiny amounts of the cryptocurrency to countless people. One of them was angel investor Garry Tan, who became one of Coinbase’s first backers. His $300,000 bet turned into $2.4 billion yesterday.

In an interview with Jason Calacanis on This Week in Startups, Armstrong emphasized the importance of entrepreneurs being scrappy and doing whatever it takes to get the job done. His original approach to investors, repeated countless times, paid off in a major way and Coinbase was accepted to Y Combinator, the most prestigious startup accelerator in Silicon Valley. Armstrong’s resourcefulness and persistence definitely inspire me.

To build a major business, Armstrong had to make sure not to run afoul of regulators. Unlike, for example, a social media app, finance is heavily regulated. Armstrong ditched the anonymity most people expect from cryptocurrencies, abiding by “know your customer laws.” In turn, he offered users a much more secure way to store their cryptocurrencies:

The selling proposition here is security—security conspicuously lacking at some of the exchanges with which Coinbase has competed. The Mt. Gox exchange in Japan went bust in 2014 after hackers spirited away coins worth $480 million. Customers of QuadrigaCX, which was one of Canada’s largest exchanges, have been unable to retrieve $150 million in crypto since the founder supposedly died suddenly in December 2018, holding the only set of keys to unlock their money. They now want the body exhumed.

Armstrong wasn’t afraid to reimagine the crypto business in a way that could grow big, and he doggedly pursued anyone who he thought could help him do it. I find his extraordinary career quite instructive.

For more on Coinbase and crytocurrencies, check out these posts:

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

In 2012, investor Garry Tan got an e-mail. A young Airbnb engineer named Brian Armstrong had sent him a tiny fraction of a bitcoin, worth just a few cents. But this message piqued his curiosity. How many people send you money for nothing?

Tan happened to be one of the few people other than Armstrong paying attention to bitcoin at the time. The digital currency had only been in use since 2009. Tan had actually bought some before, using a janky website called Mount Gox. The process was frustrating. He knew there had to be a better way.

So Tan tried Armstrong’s new system. He found buying and selling bitcoin a breeze, and happily wrote a $300,000 check to Armstrong’s nascent company, Bitbank. That company became Coinbase, which went public today on the Nasdaq. Its current market cap is nearly $100 billion.

Tan’s initial investment is now worth $2.4 billion, making him one of the wealthiest men in America. But why did he spot Coinbase when other investors turned them down?

Tan’s familiarity with cryptocurrencies and the problems in buying and selling them was a major factor. He could see Coinbase’s technology was better than what he and other users had had to put up with, so using it would be a no brainer for others. He had also studied the removal of the gold standard in 1971 and was convinced fiat money was risky.

What do I take from this experience, as an investor? It tells me to look for products in sectors I’m familiar with, and use the product myself if possible. And if a product solves a problem for me, it’s likely to solve it for others as well.

It also makes me want to read widely and keep up with current technologies as much as possible. The more familiar I am with the new technologies businesses are using, the more good shots at a great investment I will have.

I hope to have my own 6,000x bet some day!

For more on startups, venture capital and crypto, check out these posts:

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Venture Funding Just Doubled in 1 Year

I came across an incredible stat last night:

Worldwide venture funding has nearly doubled YoY reaching $125B and grew by half QoQ in Q1 2021, according to Crunchbase. On average, two startups crossed the unicorn valuation threshold each working day during the first three months of the year.

Users increasing their engagement with online tools due to the pandemic, along with easier exits via Special Purpose Acquisition Vehicles (SPACs), were two big factors in this extraordinary increase. I’d also be willing to bet that a big jump in the money supply, which is showing up everywhere from meme stocks to cryptocurrenices, is a factor.

In startups I’m looking at, I’m seeing valuations in the $10-15 million range even on seed stage companies. A few years ago, that might have been $5-6 million. I can’t say I love those higher prices, but if a company achieves a valuation of $1 billion (not to mention $10 or $100 billion), whether you got in at a $5 or $15 million valuation may not matter.

I’ll be watching to see if these trends continue or if the industry is setting itself up for a crash. With consumers becoming more and more used to doing everything online during 2020, along with loose monetary policy, I think that any downturn is probably quite a ways off.

For more on venture capital and startups, check out these posts:

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Photo: “Rocket Launch SpaceX” by Schwabenknipser is licensed under CC BY-ND 2.0

Key Metrics for Startups: Consumer vs. Enterprise SaaS

I listened to a fascinating podcast this morning in which Jason Calacanis, an early investor in companies including Uber and Calm, broke down how to measure startup success. The key metrics depend on what kind of company you’re looking at:

Consumer companies:

  • Of the biggest users, how many are retained? For example, if someone used the app 3 times a week on average last month, how likely were they to return this month? Much of your app engagement is driven by the most active users.
  • What is the customer acquisition cost versus the revenue from each customer? Half to two thirds of the spending of fast growing consumer companies is marketing, even outpacing staff salaries! And that makes sense if you’re customer acquisition cost is $50 but you can get $100 from them. You should do that all day. This is also relevant for SaaS startups.
  • For marketplaces, how often do transactions happen? Higher revenue transactions, like booking an Airbnb, can be less frequent. Low revenue transactions, like taking an Uber, need to be more frequent.
  • Also for marketplaces: what is the take rate? How much money do you get from each transaction?

Enterprise Software as a Service (SaaS) companies:

  • How many customers “land and expand”? Since enterprise SaaS tends to have a lower churn rate (customers leaving), how many become customers and then buy more licenses (“seats”) for more of their staff is key. Another way customers can expand is if you start selling more products and they buy those too.
  • Churn rate is less relevant. You don’t see as many customers cancelling because businesses put more consideration into a software purchase and then rely on it for their company’s success. A consumer is much more likely to take a flier on a Hulu membership than a company is to do so on a SaaS product. This means if you keep selling enough licenses and new, adjacent products to existing customers, you don’t even need to increase customer count much. This is less true for consumer startups.

Bonus: Dating apps face some special challenges. Facebook and Instagram sometimes ban them from advertising, and it’s very difficult to get them approved in the Apple app store. This may be because some are used to scam people and companies want to protect their users.

Some great info in this podcast! I’ll definitely be using it to guide my investment decisions. On the whole, SaaS seems a lot easier. Customers are less fickle, have deeper pockets, and are more willing to pay for something than consumers who have been trained that if it’s on the internet, it’s free.

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Check out the Stuff I Use page for some great deals on products and services I use to improve my health and productivity. They just might help you too! 

Photo: CEO of hot startup Clubhouse, “Paul Davison” by jdlasica is licensed under CC BY 2.0