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.

How I monetized and sold an abandoned side project for $20,000

The Origin Story

I've always wanted to be an entrepreneur but never succeeded. I often had business ideas, made a landing page, and told my buddies. Never got customers.

In April 2021, I decided to try again with a new strategy. I noticed that I had trouble acquiring an initial set of customers, so I wanted to start by acquiring a product that had a small user base that I could grow.

I found a SaaS marketplace called MicroAcquire.com where you could buy and sell SaaS products. I liked Shareit.video, an online Loom-like screen recorder.

Shareit.video didn't generate revenue, but 50 people visited daily to record screencasts.

Purchasing a Failed Side Project

I eventually bought Shareit.video for $12,000 from its owner.

$12,000 was probably too much for a website without revenue or registered users.

I thought time was most important. I could have recreated the website, but it would take months. $12,000 would give me an organized code base and a working product with a few users to monetize.

I considered buying a screen recording website and trying to grow it versus buying a new car or investing in crypto with the $12K.

Buying the website would make me a real entrepreneur, which I wanted more than anything.

Putting down so much money would force me to commit to the project and prevent me from quitting too soon.

A Year of Development

I rebranded the website to be called RecordJoy and worked on it with my cousin for about a year. Within a year, we made $5000 and had 3000 users.

We spent $3500 on ads, hosting, and software to run the business.

AppSumo promoted our $120 Life Time Deal in exchange for 30% of the revenue.

We put RecordJoy on maintenance mode after 6 months because we couldn't find a scalable user acquisition channel.

We improved SEO and redesigned our landing page, but nothing worked.

Despite not being able to grow RecordJoy any further, I had already learned so much from working on the project so I was fine with putting it on maintenance mode. RecordJoy still made $500 a month, which was great lunch money.

Getting Taken Over

One of our customers emailed me asking for some feature requests and I replied that we weren’t going to add any more features in the near future. They asked if we'd sell.

We got on a call with the customer and I asked if he would be interested in buying RecordJoy for 15k. The customer wanted around $8k but would consider it.

Since we were negotiating with one buyer, we put RecordJoy on MicroAcquire to see if there were other offers.

We quickly received 10+ offers. We got 18.5k. There was also about $1000 in AppSumo that we could not withdraw, so we agreed to transfer that over for $600 since about 40% of our sales on AppSumo usually end up being refunded.

Lessons Learned

First, create an acquisition channel

We couldn't discover a scalable acquisition route for RecordJoy. If I had to start another project, I'd develop a robust acquisition channel first. It might be LinkedIn, Medium, or YouTube.

Purchase Power of the Buyer Affects Acquisition Price

Some of the buyers we spoke to were individuals looking to buy side projects, as well as companies looking to launch a new product category. Individual buyers had less budgets than organizations.

Customers of AppSumo vary.

AppSumo customers value lifetime deals and low prices, which may not be a good way to build a business with recurring revenue. Designed for AppSumo users, your product may not connect with other users.

Try to increase acquisition trust

Acquisition often fails. The buyer can go cold feet, cease communicating, or run away with your stuff. Trusting the buyer ensures a smooth asset exchange. First acquisition meeting was unpleasant and price negotiation was tight. In later meetings, we spent the first few minutes trying to get to know the buyer’s motivations and background before jumping into the negotiation, which helped build trust.

Operating expenses can reduce your earnings.

Monitor operating costs. We were really happy when we withdrew the $5000 we made from AppSumo and Stripe until we realized that we had spent $3500 in operating fees. Spend money on software and consultants to help you understand what to build.

Don't overspend on advertising

We invested $1500 on Google Ads but made little money. For a side project, it’s better to focus on organic traffic from SEO rather than paid ads unless you know your ads are going to have a positive ROI.

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.

WTF is wrong with you people?

When I was laid off as editor of my town's daily newspaper, I went silent on social media. I knew it was coming and had been quietly removing personal items each day, but the pain was intense.

I posted a day later. I didn't bad-mouth GateHouse Media but expressed my sadness at leaving the newspaper industry, pride in my accomplishments, and hope for success in another industry.

Normal job-loss response.

What do you recognize as abnormal?

The bullshit I’ve been reading from laid-off folks on LinkedIn.

If you're there, you know. Many Twitter or Facebook/Meta employees recently lost their jobs.

Well, many of them did not “lose their job,” actually. They were “impacted by the layoffs” at their former employer. I keep seeing that phrase.

Why don’t they want to actually say it? Why the euphemism?

Many are excited about the opportunities ahead. The jobless deny being sad.

They're ecstatic! They have big plans.

Hope so. Sincerely! Being laid off stinks, especially if, like me, your skills are obsolete. It's worse if, like me, you're too old to start a new career. Ageism exists despite denials.

Nowadays, professionalism seems to demand psychotic levels of fake optimism.

Why? Life is unpredictable. That's indisputable. You shouldn't constantly complain or cry in public, but you also shouldn't pretend everything's great.

It makes you look psychotic, not positive. It's like saying at work:

“I was impacted by the death of my spouse of 20 years this week, and many of you have reached out to me, expressing your sympathy. However, I’m choosing to remember the amazing things we shared. I feel confident that there is another marriage out there for me, and after taking a quiet weekend trip to reset myself, I’ll be out there looking for the next great marital adventure! #staypositive #available #opentolove

Also:

“Now looking for our next #dreamhome after our entire neighborhood was demolished by a wildfire last night. We feel so lucky to have lived near so many amazing and inspirational neighbors, all of whom we will miss as we go on our next housing adventure. The best house for us is yet to come! If you have a great neighborhood you’d recommend, please feel free to reach out and touch base with us! #newhouse #newneighborhood #newlife

Admit it. That’s creepy.

The constant optimism makes me feel sick to my stomach.

Viscerally.

I hate fakes.

Imagine a fake wood grain desk. Wouldn't it be better if the designer accepted that it's plastic and went with that?

Real is better but not always nice. When something isn't nice, you don't have to go into detail, but you also shouldn't pretend it's great.

How to announce your job loss to the world.

Do not pretend to be happy, but don't cry and drink vodka all afternoon.

Say you loved your job, and that you're looking for new opportunities.

Yes, if you'll miss your coworkers. Otherwise, don't badmouth. No bridge-burning!

Please specify the job you want. You may want to pivot.

Alternatively, try this.

You could always flame out.

If you've pushed yourself too far into toxic positivity, you may be ready to burn it all down. If so, make it worthwhile by writing something like this:

Well, I was shitcanned by the losers at #Acme today. That bitch Linda in HR threw me under the bus just because she saw that one of my “friends” tagged me in some beach pics on social media after I called in sick with Covid. The good thing is I will no longer have to watch my ass around that #asspincher Ron in accounting, but I’m sad that I will no longer have a cushy job with high pay or access to the primo office supplies I’ve been sneaking home for the last five years. (Those gel pens were the best!) I am going to be taking some time off to enjoy my unemployment and hammer down shots of Jägermeister but in about five months I’ll be looking for anything easy with high pay and great benefits. Reach out if you can help! #officesupplies #unemploymentrocks #drinkinglikeagirlboss #acmesucks

It beats the fake positivity.

A reading list for successful people

Elon Musk reads and talks. So, one learns. Many brilliant individuals & amazing literature.

This article recommends 3 Elon Musk novels. All of them helped me succeed. Hope they'll help you.

Douglas Adams's The Hitchhiker's Guide to the Galaxy

Page Count: 193
Rating on Goodreads: 4.23

Arthur Dent is pulled off Earth by a buddy seconds before it's razed for a cosmic motorway. The trio hitchhikes through space and gets into problems.

I initially read Hitchhiker's as a child. To evade my mum, I'd read with a flashlight under the covers. She'd scold at me for not sleeping on school nights when she found out. Oops.

The Hitchhiker's Guide to the Galaxy is lighthearted science fiction.

My favorite book quotes are:

• “Space is big. You won’t believe how vastly, hugely, mind-bogglingly big it is. I mean, you may think it’s a long way down the road to the chemist’s, but that’s just peanuts to space.”

• “Far out in the uncharted backwaters of the unfashionable end of the western spiral arm of the Galaxy lies a small unregarded yellow sun. Orbiting this at a distance of roughly ninety-two million miles is an utterly insignificant little blue-green planet whose ape-descended life forms are so amazingly primitive that they still think digital watches are a pretty neat idea.”

• “On planet Earth, man had always assumed that he was more intelligent than dolphins because he had achieved so much — the wheel, New York, wars, and so on — whilst all the dolphins had ever done was muck about in the water having a good time. But conversely, the dolphins had always believed that they were far more intelligent than man — for precisely the same reasons.”

the Sun Tzu book The Art Of War

Page Count: 273
Rating on Goodreads: 3.97

It's a classic. You may apply The Art of War's ideas to (nearly) every facet of life. Ex:

• Pick your fights.

• Keep in mind that timing is crucial.

• Create a backup plan in case something goes wrong.

• Obstacles provide us a chance to adapt and change.

This book was my first. Since then, I'm a more strategic entrepreneur. Excellent book. And read it ASAP!

My favorite book quotes are:

• “Victorious warriors win first and then go to war, while defeated warriors go to war first and then seek to win.”

• “Engage people with what they expect; it is what they are able to discern and confirms their projections. It settles them into predictable patterns of response, occupying their minds while you wait for the extraordinary moment — that which they cannot anticipate.”

• “If you know the enemy and know yourself, you need not fear the result of a hundred battles. If you know yourself but not the enemy, for every victory gained, you will also suffer a defeat. If you know neither the enemy nor yourself, you will succumb in every battle.”

Peter Thiel's book Zero to One

Page Count: 195
Rating on Goodreads: 4.18

Peter argues the best money-making strategies are typically unproven. Entrepreneurship should never have a defined path to success. Whoever says differently is lying.

Zero to One explores technology and society. Peter is a philosophy major and law school graduate, which informs the work.

Peters' ideas, depth, and intellect stood out in Zero to One. It's a top business book.

My favorite book quotes are:

• “The most valuable businesses of coming decades will be built by entrepreneurs who seek to empower people rather than try to make them obsolete.”

• “The next Bill Gates will not build an operating system. The next Larry Page or Sergey Brin won’t make a search engine. And the next Mark Zuckerberg won’t create a social network. If you are copying these guys, you aren’t learning from them.”

• “If your goal is to never make a mistake in your life, you shouldn’t look for secrets. The prospect of being lonely but right — dedicating your life to something that no one else believes in — is already hard. The prospect of being lonely and wrong can be unbearable.”