Here is the ugly stuff, read this if you have a founder in your life or are trying to become one. Your call.

#1 You'll try to talk yourself to sleep, but it won't always work.

As founders, we're all driven. Good and bad, you're restless. Success requires resistance and discipline. Your startup will be on your mind 24/7, and not everyone will have the patience to listen to your worries, ideas, and coffee runs. You become more self-sufficient than ever before.

#2 No one will understand what you're going through unless they've been a founder.

Some of my closest friends don't understand the work that goes into starting a business, and we can't blame them.

#3 You'll feel alienated.

Your problems aren't common; calling your bestie won't help. You must search hard for the right resources. It alienates you from conversations you no longer relate to. (No 4th of July, no long weekends!)

#4 Since you're your "own boss," people assume you have lots of free time.

Do you agree? I was on a webinar with lots of new entrepreneurs, and one woman said, "I started my own business so I could have more time for myself." This may be true for some lucky people, and you can be flexible with your schedule. If you want your business to succeed, you'll probably be its slave for a while.

#5 No time for illness or family emergencies.

Both last month. Oh, no! Physically and emotionally withdrawing at the worst times will give you perspective. I learned this the hard way because I was too stubborn to postpone an important interview. I thought if I rested all day and only took one call, I'd be fine. Nope. I had a fever and my mind wasn't as sharp, so my performance and audience interaction suffered. Nope. Better to delay than miss out.

Oh, and setting a "OoO" makes you cringe.

#6 Good luck with your mental health, perfectionists.

When building a startup, it's difficult to accept that there won't be enough time to do everything. You can't make them all, not perfectly. You must learn to accept things that are done but not perfect.

#7 As a founder, you'll make mistakes, but you'll want to make them quickly so you can learn.

Hard lessons are learned quicker. You'll need to pivot and try new things often; some won't work, and it's best to discover them sooner rather than later.

#8 Pyramid schemes abound.

I didn't realize how bad it was until I started a company. You must spy and constantly research. As a founder, you'll receive many emails from people claiming to "support" you. Be wary and keep your eyes open. When it's too good to be true. Some "companies" will try to get you to pay for "competitions" to "pitch at events." Don't do it.

#9 Keep your competitor research to a minimum.

Actually, competition is good. It means there's a market for those solutions. However, this can be mentally exhausting too. Learn about their geography and updates, but that's it.

#10 You'll feel guilty taking vacation.

I don't know what to say, but I no longer enjoy watching TV, and that's okay. Pay attention to things that enrich you, bring you joy, and have fun. It boosts creativity.

Being a startup founder may be one of the hardest professional challenges you face, but it's also a great learning experience. Your passion will take you places you never imagined and open doors to opportunities you wouldn't have otherwise. You'll meet amazing people. No regrets, no complaints. It's a roller coaster, but the good days are great.

Miss anything? Comment below

Most don't understand the issue until it's too late.

My first startup was what entrepreneurs call the hardest. A two-sided marketplace.

Two-sided marketplaces are the hardest startups because founders must solve the chicken or the egg conundrum.

A two-sided marketplace needs suppliers and buyers. Without suppliers, buyers won't come. Without buyers, suppliers won't come. An empty marketplace and a founder striving to gain momentum result.

My first venture made me a struggling founder seeking to achieve traction for a two-sided marketplace. The company failed, and I vowed never to start another like it.

I didn’t. Unfortunately, my second venture was almost as hard. It failed like the second-hardest startup.

What kind of startup is the second-hardest?

The second-hardest startup, which is almost as hard to develop, is rarely discussed in the startup community. Because of this, I predict more founders fail each year trying to develop the second-toughest startup than the hardest.

Fairly, I have no proof. I see many startups, so I have enough of firsthand experience. From what I've seen, for every entrepreneur developing a two-sided marketplace, I'll meet at least 10 building this other challenging startup.

I'll describe a startup I just met with its two co-founders to explain the second hardest sort of startup and why it's so hard. They created a financial literacy software for parents of high schoolers.

The issue appears plausible. Children struggle with money. Parents must teach financial responsibility. Problems?

It's possible.

Buyers and users are different.

Buyer-user mismatch.

The financial literacy app I described above targets parents. The parent doesn't utilize the app. Child is end-user. That may not seem like much, but it makes customer and user acquisition and onboarding difficult for founders.

The difficulty of a buyer-user imbalance

The company developing a product faces a substantial operational burden when the buyer and end customer are different. Consider classic firms where the buyer is the end user to appreciate that responsibility.

Entrepreneurs selling directly to end users must educate them about the product's benefits and use. Each demands a lot of time, effort, and resources.

Imagine selling a financial literacy app where the buyer and user are different. To make the first sale, the entrepreneur must establish all the items I mentioned above. After selling, the entrepreneur must supply a fresh set of resources to teach, educate, or train end-users.

Thus, a startup with a buyer-user mismatch must market, sell, and train two organizations at once, requiring twice the work with the same resources.

The second hardest startup is hard for reasons other than the chicken-or-the-egg conundrum. It takes a lot of creativity and luck to solve the chicken-or-egg conundrum.

The buyer-user mismatch problem cannot be overcome by innovation or luck. Buyer-user mismatches must be solved by force. Simply said, when a product buyer is different from an end-user, founders have a lot more work. If they can't work extra, their companies fail.

Christopher Janz of Point Nine Capital created the SaaS napkin in 2016. This post shows how founders have raised cash in the last 6 years. View raw data.

Round size

Unsurprisingly, round sizes have expanded and will taper down in 2022. In 2016, pre-seed rounds were $200k to $500k; currently, they're $1-$2m. Despite the macroeconomic scenario, Series A have expanded from $3m to $12m in 2016 to $6m and $18m in 2022.

Valuation

There are hints that valuations are rebounding this year. Pre-seed valuations in 2022 are $12m from $3m in 2016, and Series B prices are $270m from $100m in 2016.

Compared to public SaaS multiples, Series B valuations more closely reflect the market, but Seed and Series A prices seem to be inflated regardless of the market.

I'd like to know how each annual cohort performed for investors, based on the year they invested and the valuations. I can't access this information.

ARR

Seed firms' ARR forecasts have risen from $0 to $0.6m to $0 to $1m. 2016 expected $1.2m to $3m, 2021 $0.5m to $4m, and this year $0.5m to $2.5m, suggesting that Series A firms may raise with less ARR today. Series B minutes fell from $4.2m to $3m.

Capitalization Rate

2022 is the year that VCs start discussing capital efficiency in portfolio meetings. Given the economic shift in the markets and the stealthy VC meltdown, it's not surprising. Christopher Janz added capital efficiency to the SaaS Napkin as a new statistic for Series A (3.5x) and Series B. (2.5x). Your investors must live under a rock if they haven't asked about capital efficiency. If you're unsure:

The Capital Efficiency Ratio is the ratio of how much a company has spent growing revenue and how much they’re receiving in return. It is the broadest measure of company effectiveness in generating ARR

What next?

No one knows what's next, including me. All startup and growing enterprises around me are tightening their belts and extending their runways in anticipation of a difficult fundraising ride. If you're wanting to raise money but can wait, wait till the market is more stable and access to money is easier.

From 1984 until 2011, he ran Apple using the same template.

What is a founder CEO's most crucial skill?

Presentation, communication, and sales

As a Business Angel Investor, I saw many pitch presentations and met with investors one-on-one to promote my companies.

There is always the conception of “Investors have to invest,” so there is no need to care about the presentation.

It's false. Nobody must invest. Many investors believe that entrepreneurs must convince them to invest in their business.

Sometimes — like in 2018–2022 — too much money enters the market, and everyone makes good money.

Do you recall the Buy Now, Pay Later Movement? This amazing narrative had no return potential. Only buyers who couldn't acquire financing elsewhere shopped at these companies.

Klarna's failing business concept led to high valuations.

Investors become more cautious when the economy falters. 2022 sees rising inflation, interest rates, wars, and civil instability. It's like the apocalypse's four horsemen have arrived.

Storytelling is important in rough economies.

When investors draw back, how can entrepreneurs stand out?

In Q2/2022, every study I've read said:

Investors cease investing

Deals are down in almost all IT industries from previous quarters.

What do founders need to do?

Differentiate yourself.

Storytelling talents help.

The Steve Jobs Way

Every time I watch a Steve Jobs presentation, I'm enthralled.

I'm a techie. Everything technical interests me. But, I skim most presentations.

What's Steve Jobs's secret?

Steve Jobs created Apple in 1976 and made it a profitable software and hardware firm in the 1980s. Macintosh goods couldn't beat IBM's. This mistake sacked him in 1985.

Before rejoining Apple in 1997, Steve Jobs founded Next Inc. and Pixar.

From then on, Apple became America's most valuable firm.

Steve Jobs understood people's needs. He said:

“People don’t know what they want until you show it to them. That’s why I never rely on market research. Our task is to read things that are not yet on the page.”

In his opinion, people talk about problems. A lot. Entrepreneurs must learn what the population's pressing problems are and create a solution.

Steve Jobs showed people what they needed before they realized it.

I'll explain:

Present a Big Vision

Steve Jobs starts every presentation by describing his long-term goals for Apple.

1984's Macintosh presentation set up David vs. Goliath. In a George Orwell-style dystopia, IBM computers were bad. It was 1984.

Apple will save the world, like Jedis.

Why do customers and investors like Big Vision?

People want a wider perspective, I think. Humans love improving the planet.

Apple users often cite emotional reasons for buying the brand.

Revolutionizing several industries with breakthrough inventions

Establish Authority

Everyone knows Apple in 2022. It's hard to find folks who confuse Apple with an apple around the world.

Apple wasn't as famous as it is today until Steve Jobs left in 2011.

Most entrepreneurs lack experience. They may market their company or items to folks who haven't heard of it.

Steve Jobs presented the company's historical accomplishments to overcome opposition.

In his presentation of the first iPhone, he talked about the Apple Macintosh, which altered the computing sector, and the iPod, which changed the music industry.

People who have never heard of Apple feel like they're seeing a winner. It raises expectations that the new product will be game-changing and must-have.

The Big Reveal

A pitch or product presentation always has something new.

Steve Jobs doesn't only demonstrate the product. I don't think he'd skip the major point of a company presentation.

He consistently discusses present market solutions, their faults, and a better consumer solution.

No solution exists yet.

It's a multi-faceted play:

• It's comparing the new product to something familiar. This makes novelty and the product more relatable.

• Describe a desirable solution.

• He's funny. He demonstrated an iPod with an 80s phone dial in his iPhone presentation.

Then he reveals the new product. Macintosh presented itself.

Show the benefits

He outlines what Apple is doing differently after demonstrating the product.

How do you distinguish from others? The Big Breakthrough Presentation.

A few hundred slides might list all benefits.

Everyone would fall asleep. Have you ever had similar presentations?

When the brain is overloaded with knowledge, the limbic system changes to other duties, like lunch planning.

What should a speaker do? There's a classic proverb:

“Tell me and I forget, teach me and I may remember, involve me and I learn” (— Not Benjamin Franklin).

Steve Jobs showcased the product live.

Again, using ordinary scenarios to highlight the product's benefits makes it relatable.

The 2010 iPad Presentation uses this technique.

Invite the Team and Let Them Run the Presentation

CEOs spend most time outside the organization. Many companies elect to have only one presenter.

It sends the incorrect message to investors. Product presentations should always include the whole team.

Let me explain why.

Companies needing investment money frequently have shaky business strategies or no product-market fit or robust corporate structure.

Investors solely bet on a team's ability to implement ideas and make a profit.

Early team involvement helps investors understand the company's drivers. Travel costs are worthwhile.

But why for product presentations?

Presenters of varied ages, genders, social backgrounds, and skillsets are relatable. CEOs want relatable products.

Some customers may not believe a white man's message. A black woman's message may be more accepted.

Make the story relatable when you have the best product that solves people's concerns.

Best example: 1984 Macintosh presentation with development team panel.

What is the largest error people make when companies fail?

Saving money on the corporate and product presentation.

Invite your team to five partner meetings when five investors are shortlisted.

Rehearse the presentation till it's natural. Let the team speak.

Successful presentations require structure, rehearsal, and a team. Steve Jobs nailed it.

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A few days ago, I was discussing dall-e with two art and tech pals. One artist acquaintance said she knew a frightened illustrator. Would the ability to create anything with a click derail her career? The artist feared this. My curator friend smiled and said this has always been a dread among artists. When the camera was invented, didn't painters say this? Even in the Instagram era, painting exists.

When art and technology collide, there's room for innovation, experimentation, and fear — especially if the technology replicates or replaces art making. What is art's future with dall-e? How does technology affect music, beyond visual art? Recently, I saw "ABBA Voyage," a holographic ABBA concert in London.

"Abba voyage?" my phone asked in early March. A Gen X friend I met through a fashion blogging ring texted me.

"What's abba Voyage?" I asked while opening my front door with keys and coffee.

We're going! Marti, visiting London, took me to a show.

"Absolutely no ABBA songs here." I responded.

My parents didn't play ABBA much, so I don't know much about them. Dad liked Jimi Hendrix, Cream, Deep Purple, and New Orleans jazz. Marti told me ABBA Voyage was a holographic ABBA show with a live band.

The show was fun, extraordinary fun. Nearly everyone on the dance floor wore wigs, ankle-breaking platforms, sequins, and bellbottoms. I saw some millennials and Zoomers among the boomers.

I was intoxicated by the experience.

Automatons date back to the 18th-century mechanical turk. The mechanical turk was a chess automaton operated by a person. The mechanical turk seemed to perform like a human without human intervention, but it required a human in the loop to work properly.

Humans have used non-humans in entertainment for centuries, such as puppets, shadow play, and smoke and mirrors. A show can have animatronic, technological, and non-technological elements, and a live show can blur real and illusion. From medieval puppet shows to mechanical turks to AI filters, bots, and holograms, entertainment has evolved over time.

I'm not a hologram skeptic, but I'm skeptical of technology, especially since I work with it. I love live performances, I love hearing singers breathe, forget lines, and make jokes. Live shows are my favorite because I love watching performers make mistakes or interact with the audience. ABBA Voyage was different.

Marti and I traveled to Manchester after ABBA Voyage to see Liam Gallagher. Similar but different vibe. Similar in that thousands dressed up for the show. ABBA's energy was dizzying. 90s chic replaced sequins in the crowd. Doc Martens, nylon jackets, bucket hats, shaggy hair. The Charlatans and Liam Gallagher opened and closed, respectively. Fireworks. Incredible. People went crazy. Yelling exhausted my voice.

This week in music featured AI-enabled holograms and a decades-old rocker. Both are warm and gooey in our memories.

After seeing both, I'm wondering if we need AI hologram shows. Why? Is it good?

Like everything tech-related, my answer is "maybe." Because context and performance matter. Liam Gallagher and ABBA both had great, different shows.

For a hologram to work, it must be impossible and big. It must be big, showy, and improbable to justify a hologram. It must feel...expensive, like a stadium pop show. According to a quick search, ABBA broke up on bad terms. Reuniting is unlikely. This is also why Prince or Tupac hologram shows work. We can only engage with their legacy through covers or...holograms.

I drove around listening to the radio a few weeks ago. "Dreaming of You" by Selena played. Selena's music defined my childhood. I sang along and turned up the volume (or as loud as my husband would allow me while driving on the highway).

I discovered Selena's music six months after her death, so I never saw her perform live. My babysitter Melissa played me her album after I moved to Houston. Melissa took me to see the Selena movie five times when it came out. I quickly wore out my VHS copy. I constantly sang "Bibi Bibi Bom Bom" and "Como la Flor." I love Selena. A Selena hologram? Yes, probably.

Instagram advertised a cellist's Arthur Russell tribute show. Russell is another deceased artist I love. I almost walked down the aisle to "This is How We Walk on the Moon," but our cellist couldn't find it. Instead, I walked to Magnetic Fields' "The Book of Love." I "discovered" Russell after a friend introduced me to his music a few years ago.

I use these as analogies for the Liam Gallagher and ABBA concerts.

You have no idea how much I'd pay to see a hologram of Selena's 1995 Houston Livestock Show and Rodeo concert. Arthur Russell's hologram is unnecessary. Russell's work was intimate and performance-based. We can't separate his life from his legacy; popular audiences overlooked his genius. He died of AIDS broke. Like Selena, he died prematurely. Given his music and history, another performer would be a better choice than a hologram. He's no Selena. Selena could have rivaled Beyonce.

Pop shows' size works for holograms. Along with ABBA holograms, there was an anime movie and a light show that would put Tron to shame. ABBA created a tourable stadium show. The event was lavish, expensive, and well-planned. Pop, unlike rock, isn't gritty. Liam Gallagher hologram? No longer impossible, it wouldn't work. He's touring. I'm not sure if a rockstar alone should be rendered as a hologram; it was the show that made ABBA a hologram.

Holograms, like AI, are part of the future of entertainment, but not all of it. Because only modern interpretations of Arthur Russell's work reveal his legacy. That's his legacy.

Large-scale arena performers may use holograms in the future, but the experience must be impossible. A teacher once said that the only way to convey emotion in opera is through song, and I feel the same way about holograms, AR, VR, and mixed reality. A story's impossibility must make sense, like in opera. Impossibility and bombastic performance must be present for an immersive element to "work." ABBA was an impossible and improbable experience, which made it magical. It helped the holographic show work.

Marti told me about ABBA Voyage. She said it was a great concert. Marti has worked in music since the 1990s. She's a music expert; she's seen many shows.

Ai isn't a god or sentient, and the ABBA holograms aren't real. The renderings were glassy-eyed, flat, and robotic, like the Polar Express or the Jaws shark. Even today, the uncanny valley is insurmountable. We know it's not real because it's not about reality. It was about a suspended moment and performance feelings.

I knew this was impossible, an 'unreal' experience, but the emotions I felt were real, like watching a movie or tv show. Perhaps this is one of the better uses of AI, like CGI and special effects, like the beauty of entertainment- we were enraptured and entertained for hours. I've been playing ABBA since then.