5 VC investment criteria

I reviewed 200 startup business concepts last week. Brainache.

The enterprises sold various goods and services. The concepts were achingly similar: give us money, we'll produce a product, then get more to expand. No different from daily plans and pitches.

Most of those 200 plans sounded plausible. But 10% looked venture-worthy. 90% of startups need alternatives to venture finance.

With the success of VC-backed businesses and the growth of venture funds, a common misperception is that investors would fund any decent company idea. Finding investors that believe in the firm and founders is the key to funding.

Incorrect. Venture capital needs investing in certain enterprises. If your startup doesn't match the model, as most early-stage startups don't, you can revise your business plan or locate another source of capital.

Before spending six months pitching angels and VCs, make sure your startup fits these criteria.

Likely to generate $100 million in sales

First, I check the income predictions in a pitch deck. If it doesn't display $100M, don't bother.

The math doesn't work for venture financing in smaller businesses.

Say a fund invests $1 million in a startup valued at $5 million that is later acquired for $20 million. That's a win everyone should celebrate. Most VCs don't care.

Consider a $100M fund. The fund must reach $360M in 7 years with a 20% return. Only 20-30 investments are possible. 90% of the investments will fail, hence the 23 winners must return $100M-$200M apiece. $15M isn't worth the work.

Angel investors and tiny funds use the same ideas as venture funds, but their smaller scale affects the calculations. If a company can support its growth through exit on less than $2M in angel financing, it must have $25M in revenues before large companies will consider acquiring it.

Aiming for Hypergrowth

A startup's size isn't enough. It must expand fast.

Developing a great business takes time. Complex technology must be constructed and tested, a nationwide expansion must be built, or production procedures must go from lab to pilot to factories. These can be enormous, world-changing corporations, but venture investment is difficult.

The normal 10-year venture fund life. Investments are made during first 3–4 years.. 610 years pass between investment and fund dissolution. Funds need their investments to exit within 5 years, 7 at the most, therefore add a safety margin.

Longer exit times reduce ROI. A 2-fold return in a year is excellent. Loss at 2x in 7 years.

Lastly, VCs must prove success to raise their next capital. The 2nd fund is raised from 1st fund portfolio increases. Third fund is raised using 1st fund's cash return. Fund managers must raise new money quickly to keep their jobs.

Branding or technology that is protected

No big firm will buy a startup at a high price if they can produce a competing product for less. Their development teams, consumer base, and sales and marketing channels are large. Who needs you?

Patents, specialist knowledge, or brand name are the only answers. The acquirer buys this, not the thing.

I've heard of several promising startups. It's not a decent investment if there's no exit strategy.

A company that installs EV charging stations in apartments and shopping areas is an example. It's profitable, repeatable, and big. A terrific company. Not a startup.

This building company's operations aren't secret. No technology to protect, no special information competitors can't figure out, no go-to brand name. Despite the immense possibilities, a large construction company would be better off starting their own.

Most venture businesses build products, not services. Services can be profitable but hard to safeguard.

Probable purchase at high multiple

Once a software business proves its value, acquiring it is easy. Pharma and medtech firms have given up on their own research and instead acquire startups after regulatory permission. Many startups, especially in specialized areas, have this weakness.

That doesn't mean any lucrative $25M-plus business won't be acquired. In many businesses, the venture model requires a high exit premium.

A startup invents a new glue. 3M, BASF, Henkel, and others may buy them. Adding more adhesive to their catalogs won't boost commerce. They won't compete to buy the business. They'll only buy a startup at a profitable price. The acquisition price represents a moderate EBITDA multiple.

The company's $100M revenue presumably yields $10m in profits (assuming they’ve reached profitability at all). A $30M-$50M transaction is likely. Not terrible, but not what venture investors want after investing $25M to create a plant and develop the business.

Private equity buys profitable companies for a moderate profit multiple. It's a good exit for entrepreneurs, but not for investors seeking 10x or more what PE firms pay. If a startup offers private equity as an exit, the conversation is over.

Constructed for purchase

The startup wants a high-multiple exit. Unless the company targets $1B in revenue and does an IPO, exit means acquisition.

If they're constructing the business for acquisition or themselves, founders must decide.

If you want an indefinitely-running business, I applaud you. We need more long-term founders. Most successful organizations are founded around consumer demands, not venture capital's urge to grow fast and exit. Not venture funding.

if you don't match the venture model, what to do

VC funds moonshots. The 10% that succeed are extraordinary. Not every firm is a rocketship, and launching the wrong startup into space, even with money, will explode.

But just because your startup won't make $100M in 5 years doesn't mean it's a bad business. Most successful companies don't follow this model. It's not venture capital-friendly.

Although venture capital gets the most attention due to a few spectacular triumphs (and disasters), it's not the only or even most typical option to fund a firm.

Other ways to support your startup:

• Personal and family resources, such as credit cards, second mortgages, and lines of credit

• bootstrapping off of sales

• government funding and honors

• Private equity & project financing

• collaborating with a big business

• Including a business partner

Before pitching angels and VCs, be sure your startup qualifies. If so, include them in your pitch.

People are slowly recognizing entrepreneurship's downside.

Growing up, entrepreneurship wasn't common. High school class of 2012 had no entrepreneurs.

Businesses were different.

They had staff and a lengthy history of achievement.

I never wanted a business. It felt unattainable. My friends didn't care.

Weird.

People desired degrees to attain good jobs at big companies.

When graduated high school:

• 9 out of 10 people attend college

• Earn minimum wage (7%) working in a restaurant or retail establishment

• Or join the military (3%)

Later, entrepreneurship became a thing.

2014-ish

I was in the military and most of my high school friends were in college, so I didn't hear anything.

Entrepreneurship soared in 2015, according to Google Trends.

Then more individuals were interested. Entrepreneurship went from unusual to cool.

In 2015, it was easier than ever to build a website, run Facebook advertisements, and achieve organic social media reach.

There were several online business tools.

You didn't need to spend years or money figuring it out. Most entry barriers were gone.

Everyone wanted a side gig to escape the 95.

Small company applications have increased during the previous 10 years.

2011-2014 trend continues.

2015 adds 150,000 applications. 2016 adds 200,000. Plus 300,000 in 2017.

The graph makes it look little, but that's a considerable annual spike with no indications of stopping.

By 2021, new business apps had doubled.

Entrepreneurship will return to its early 2010s level.

I think we'll go backward in 5 years.

Entrepreneurship is half as popular as it was in 2015.

In the late 2020s and 30s, entrepreneurship will again be obscure.

Entrepreneurship's decade-long splendor is fading. People will cease escaping 9-5 and launch fewer companies.

That’s not a bad thing.

I think people have a rose-colored vision of entrepreneurship. It's fashionable. People feel that they're missing out if they're not entrepreneurial.

Reality is showing up.

People say on social media, "I knew starting a business would be hard, but not this hard."

More negative posts on entrepreneurship:

Luke adds:

Is being an entrepreneur ‘healthy’? I don’t really think so. Many like Gary V, are not role models for a well-balanced life. Despite what feel-good LinkedIn tells you the odds are against you as an entrepreneur. You have to work your face off. It’s a tough but rewarding lifestyle. So maybe let’s stop glorifying it because it takes a lot of (bleepin) work to survive a pandemic, mental health battles, and a competitive market.

Entrepreneurship is no longer a pipe dream.

It’s hard.

I went full-time in March 2020. I was done by April 2021. I had a good-paying job with perks.

When that fell through (on my start date), I had to continue my entrepreneurial path. I needed money by May 1 to pay rent.

Entrepreneurship isn't as great as many think.

Entrepreneurship is a serious business.

If you have a 9-5, the grass isn't greener here. Most people aren't telling the whole story when they post on social media or quote successful entrepreneurs.

People prefer to communicate their victories than their defeats.

Is this a bad thing?

I don’t think so.

Over the previous decade, entrepreneurship went from impossible to the finest thing ever.

It peaked in 2020-21 and is returning to reality.

Startups aren't for everyone.

If you like your job, don't quit.

Entrepreneurship won't amaze people if you quit your job.

It's irrelevant.

You're doomed.

And you'll probably make less money.

If you hate your job, quit. Change jobs and bosses. Changing jobs could net you a greater pay or better perks.

When you go solo, your paycheck and perks vanish. Did I mention you'll fail, sleep less, and stress more?

Nobody will stop you from pursuing entrepreneurship. You'll face several challenges.

Possibly.

Entrepreneurship may be romanticized for years.

Based on what I see from entrepreneurs on social media and trends, entrepreneurship is challenging and few will succeed.

I've spent over 50 hours researching one-person firms, which interest me. I've found countless one-person enterprises that made millions on the founder's determination and perseverance.

Throughout my investigation, I found three of the most outstanding one-person enterprises. These enterprises show that people who work hard and dedicate themselves to their ideas may succeed.

Eric Barone (@ConcernedApe) created Stardew Valley in 2011 to better his job prospects. Eric loved making the game, in which players inherit a farm, grow crops, raise livestock, make friends with the villagers, and form a family.

Eric handled complete game production, including 3D graphics, animations, and music, to maintain creative control. He stopped job hunting and worked 8-15 hours a day on the game.

Eric developed a Stardew Valley website and subreddit to engage with gamers and get feedback. Eric's devoted community helped him meet Steam's minimum vote requirement for single creators.

Stardew Valley sold 1 million copies in two months after Eric launched it for $15 in 2016. The game has sold 20 million copies and made $300 million.

The game's inexpensive price, outsourcing of PR, marketing, and publication, and loyal player base helped it succeed. Eric has turned down million-dollar proposals from Sony and Nintendo to sell the game and instead updates and improves it. Haunted Chocolatier is Eric's new game.

Is farming not profitable? Ask Stardew Valley creator Eric Barone.

Gary Brewer established BuiltWith to assist users find website technologies and services. BuiltWith boasts 3000 paying customers and $14 million in yearly revenue, making it a significant resource for businesses wishing to generate leads, do customer analytics, obtain business insight, compare websites, or search websites by keyword.

BuiltWith has one full-time employee, Gary, and one or two part-time contractors that help with the blog. Gary handles sales, customer service, and other company functions alone.

BuiltWith acquired popularity through blog promotions and a top Digg ranking. About Us, a domain directory, connected to BuiltWith on every domain page, boosting it. Gary introduced $295–$995 monthly subscriptions to search technology, keywords, and potential consumers in response to customer demand.

Gary uses numerous methods to manage a firm without staff. He spends one to two hours every day answering user queries, most of which are handled quickly by linking to BuiltWiths knowledge store. Gary creates step-by-step essays or videos for complex problems. Gary can focus on providing new features based on customer comments and requests since he makes it easy to unsubscribe.

BuiltWith is entirely automated and successful due to its unique approach and useful offerings. It works for Google, Meta, Amazon, and Twitter.

Digital Inspiration develops Google Documents, Sheets, and Slides plugins. Digital Inspiration, founded by Amit Agarwal, receives 5 million monthly visits and earns $10 million. 40 million individuals have downloaded Digital Inspirations plugins.

Amit started Digital Inspiration by advertising his blog at tech events and getting Indian filter blogs and other newspapers to promote his articles. Amit built plugins and promoted them on the blog once the blog acquired popularity, using ideas from comments, friends, and Reddit. Digital Inspiration has over 20 free and premium plugins.

Mail Merge, Notifications for Google Forms, YouTube Uploader, and Document Studio are some of Digital Inspiration's most popular plugins. Mail Merge allows users to send personalized emails in bulk and track email opens and clicks.

Since Amits manages Digital Inspiration alone, his success is astounding. Amit developed a successful company via hard work and creativity, despite platform dependence. His tale inspires entrepreneurs.

Let's see this once-dominant IT corporation crumble.

What's the capital of Kazakhstan? If you don't know the answer, you can probably find it by Googling. Google Search returned results for Nur-Sultan in 0.66 seconds.

Google is the best search engine I've ever used. Did you know another search engine ruled the Internet? I'm sure you guessed Yahoo!

Google's friendly UI and wide selection of services make it my top choice. Let's explore Yahoo's decline.

Yahoo!

YAHOO stands for Yet Another Hierarchically Organized Oracle. Jerry Yang and David Filo established Yahoo.

Yahoo is primarily a search engine and email provider. It offers News and an advertising platform. It was a popular website in 1995 that let people search the Internet directly. Yahoo began offering free email in 1997 by acquiring RocketMail.

According to a study, Yahoo used Google Search Engine technology until 2000 and then developed its own in 2004.

Yahoo! rejected buying Google for $1 billion

Larry Page and Sergey Brin, Google's founders, approached Yahoo in 1998 to sell Google for $1 billion so they could focus on their studies. Yahoo denied the offer, thinking it was overvalued at the time.

Yahoo realized its error and offered Google $3 billion in 2002, but Google demanded $5 billion since it was more valuable. Yahoo thought $5 billion was overpriced for the existing market.

In 2022, Google is worth $1.56 Trillion.

What happened to Yahoo!

Yahoo refused to buy Google, and Google's valuation rose, making a purchase unfeasible.

Yahoo started losing users when Google launched Gmail. Google's UI was far cleaner than Yahoo's.

Yahoo offered $1 billion to buy Facebook in July 2006, but Zuckerberg and the board sought $1.1 billion. Yahoo rejected, and Facebook's valuation rose, making it difficult to buy.

Yahoo was losing users daily while Google and Facebook gained many. Google and Facebook's popularity soared. Yahoo lost value daily.

Microsoft offered $45 billion to buy Yahoo in February 2008, but Yahoo declined. Microsoft increased its bid to $47 billion after Yahoo said it was too low, but Yahoo rejected it. Then Microsoft rejected Yahoo’s 10% bid increase in May 2008.

In 2015, Verizon bought Yahoo for $4.5 billion, and Apollo Global Management bought 90% of Yahoo's shares for $5 billion in May 2021. Verizon kept 10%.

Yahoo's opportunity to acquire Google and Facebook could have been a turning moment. It declined Microsoft's $45 billion deal in 2008 and was sold to Verizon for $4.5 billion in 2015. Poor decisions and lack of vision caused its downfall. Yahoo's aim wasn't obvious and it didn't stick to a single domain.

Hence, a corporation needs a clear vision and a leader who can see its future.

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Unleash the power of the Option key ⌥

#1 Open a link in the Private tab first.

Previously, if I needed to open a Safari link in a private window, I would:

• copied the URL with the right click command,

• choose File > New Private Window to open a private window, and

• clicked return after pasting the URL.

I've found a more straightforward way.

Right-clicking a link shows this, right?

Hold option (⌥) for:

Click Open Link in New Private Window while holding.

Finished!

#2. Instead of searching for specific characters, try this

You may use unicode for business or school. Most people Google them when they need them.

That is lengthy!

You can type some special characters just by pressing ⌥ and a key.

For instance

• ⌥+2 -> ™ (Trademark)
• ⌥+0 -> ° (Degree)
• ⌥+G -> © (Copyright)
• ⌥+= -> ≠ (Not equal to)
• ⌥+< -> ≤ (Less than or equal to)
• ⌥+> -> ≥ (Greater then or equal to)
• ⌥+/ -> ÷ (Different symbol for division)

#3 Activate Do Not Disturb silently.

Do Not Disturb when sharing my screen is awkward for me (because people may think Im trying to hide some secret notifications).

Here's another method.

Hold ⌥ and click on Time (at the extreme right on the menu-bar).

Now, DND is activated (secretly!). To turn it off, do it again.

Note: This works only for DND focus.

#4. Resize a window starting from its center

Although this is rarely useful, it is still a hidden trick.

When you resize a window, the opposite edge or corner is used as the pivot, right?

However, if you want to resize it with its center as the pivot, hold while doing so.

#5. Yes, Cut-Paste is available on Macs as well (though it is slightly different).

I call it copy-move rather than cut-paste. This is how it works.

Carry it out.

Choose a file (by clicking on it), then copy it (⌘+C).

Go to a new location on your Mac. Do you use ⌘+V to paste it? However, to move it, press ⌘+⌥+V.

This removes the file from its original location and copies it here. And it works exactly like cut-and-paste on Windows.

#6. Instantly expand all folders

Set your Mac's folders to List view.

Assume you have one folder with multiple subfolders, each of which contains multiple files. And you wanted to look at every single file that was over there.

How would you do?

You're used to clicking the ⌄ glyph near the folder and each subfolder to expand them all, right? Instead, hold down ⌥ while clicking ⌄ on the parent folder.

This is what happens next.

Everything expands.

View/Copy a file's path as an added bonus

If you want to see the path of a file in Finder, select it and hold ⌥, and you'll see it at the bottom for a moment.

To copy its path, right-click on the folder and hold down ⌥ to see this

Click on Copy <"folder name"> as Pathname to do it.

#7 "Save As"

I was irritated by the lack of "Save As" in Pages when I first got a Mac (after 15 years of being a Windows guy).

It was necessary for me to save the file as a new file, in a different location, with a different name, or both.

Unfortunately, I couldn't do it on a Mac.

However, I recently discovered that it appears when you hold ⌥ when in the File menu.

Yay!

Managers spend much time in 1:1s. Most team members meet with supervisors regularly. 1:1s can help create relationships and tackle tough topics. Few appreciate the 1:1 format's potential. Most of the time, that potential is spent on small talk, surface-level updates, and ranting (Ugh, the marketing team isn’t stepping up the way I want them to).

What if you used that time to have deeper conversations and important insights? What if change was easy?

This post introduces a new 1:1 format to help you dive deeper, faster, and develop genuine relationships without losing impact.

A 1:1 is a chat, you would assume. Why use structure to talk to a coworker? Go! I know how to talk to people. I can write. I've always written. Also, This article was edited by Zoe.

Before you discard something, ask yourself if there's a good reason not to try anything new. Is the 1:1 only a talk, or do you want extra benefits? Try the steps below to discover more.

I. Reflection (5 minutes)

Context-free, broad comments waste time and are useless. Instead, give team members 5 minutes to write these 3 prompts.

1. What's effective?

2. What is decent but could be improved?

3. What is broken or missing?

Why these? They encourage people to be honest about all their experiences. Answering these questions helps people realize something isn't working. These prompts let people consider what's working.

Why take notes? Because you get more in less time. Will you feel awkward sitting quietly while your coworker writes? Probably. Persevere. Multi-task. Take a break from your afternoon meeting marathon. Any awkwardness will pay off.

What happens? After a few minutes of light conversation, create a template like the one given here and have team members fill in their replies. You can pre-share the template (with the caveat that this isn’t meant to take much prep time). Do this with your coworker: Answer the prompts. Everyone can benefit from pondering and obtaining guidance.

This step's output.

Part II: Talk (10-20 minutes)

Most individuals can explain what they see but not what's behind an answer. You don't like a meeting. Why not? Marketing partnership is difficult. What makes working with them difficult? I don't recommend slandering coworkers. Consider how your meetings, decisions, and priorities make work harder. The excellent stuff too. You want to know what's humming so you can reproduce the magic.

First, recognize some facts.

• Real power dynamics exist. To encourage individuals to be honest, you must provide a safe environment and extend clear invites. Even then, it may take a few 1:1s for someone to feel secure enough to go there in person. It is part of your responsibility to admit that it is normal.

• Curiosity and self-disclosure are crucial. Most leaders have received training to present themselves as the authorities. However, you will both benefit more from the dialogue if you can be open and honest about your personal experience, ask questions out of real curiosity, and acknowledge the pertinent sacrifices you're making as a leader.

• Honesty without bias is difficult and important. Due to concern for the feelings of others, people frequently hold back. Or if they do point anything out, they do so in a critical manner. The key is to be open and unapologetic about what you observe while not presuming that your viewpoint is correct and that of the other person is incorrect.

Let's go into some prompts (based on genuine conversations):

• “What do you notice across your answers?”

• “What about the way you/we/they do X, Y, or Z is working well?”

• “ Will you say more about item X in ‘What’s not working?’”

• “I’m surprised there isn’t anything about Z. Why is that?”

• “All of us tend to play some role in maintaining certain patterns. How might you/we be playing a role in this pattern persisting?”

• “How might the way we meet, make decisions, or collaborate play a role in what’s currently happening?”

Consider the preceding example. What about the Monday meeting isn't working? Why? or What about the way we work with marketing makes collaboration harder? Remember to share your honest observations!

Third section: observe patterns (10-15 minutes)

Leaders desire to empower their people but don't know how. We also have many preconceptions about what empowerment means to us and how it works. The next phase in this 1:1 format will assist you and your team member comprehend team power and empowerment. This understanding can help you support and shift your team member's behavior, especially where you disagree.

How to? After discussing the stated responses, ask each team member what they can control, influence, and not control. Mark their replies. You can do the same, adding colors where you disagree.

This step's output.

Next, consider the color constellation. Discuss these questions:

• Is one color much more prevalent than the other? Why, if so?

• Are the colors for the "what's working," "what's fine," and "what's not working" categories clearly distinct? Why, if so?

• Do you have any disagreements? If yes, specifically where does your viewpoint differ? What activities do you object to? (Remember, there is no right or wrong in this. Give explicit details and ask questions with curiosity.)

Example: Based on the colors, you can ask, Is the marketing meeting's quality beyond your control? Were our marketing partners consulted? Are there any parts of team decisions we can control? We can't control people, but have we explored another decision-making method? How can we collaborate and generate governance-related information to reduce work, even if the requirement for prep can't be eliminated?

Consider the top one or two topics for this conversation. No 1:1 can cover everything, and that's OK. Focus on the present.

Part IV: Determine the next step (5 minutes)

Last, examine what this conversation means for you and your team member. It's easy to think we know the next moves when we don't.

Like what? You and your teammate answer these questions.

1. What does this signify moving ahead for me? What can I do to change this? Make requests, for instance, and see how people respond before thinking they won't be responsive.

2. What demands do I have on other people or my partners? What should I do first? E.g. Make a suggestion to marketing that we hold a monthly retrospective so we can address problems and exchange input more frequently. Include it on the meeting's agenda for next Monday.

Close the 1:1 by sharing what you noticed about the chat. Observations? Learn anything?

Yourself, you, and the 1:1

As a leader, you either reinforce or disrupt habits. Try this template if you desire greater ownership, empowerment, or creativity. Consider how you affect surrounding dynamics. How can you expect others to try something new in high-stakes scenarios, like meetings with cross-functional partners or senior stakeholders, if you won't? How can you expect deep thought and relationship if you don't encourage it in 1:1s? What pattern could this new format disrupt or reinforce?

Fight reluctance. First attempts won't be ideal, and that's OK. You'll only learn by trying.