A fascinating business conversation.

This week at Web Summit, I had mentor hour.

Mentor hour connects startups with experienced entrepreneurs.

The YC-selected founder who mentored me had grown his company to $100 million in 18 months.

I had 45 minutes to question him.

I've compiled this.

Context

Founder's name is Zack.

After working in private equity, Zack opted to acquire an MBA.

Surrounded by entrepreneurs at a prominent school, he decided to become one himself.

Unsure how to proceed, he bet on two horses.

On one side, he received an offer from folks who needed help running their startup owing to lack of time. On the other hand, he had an idea for a SaaS to start himself.

He just needed to validate it.

Validating

Since Zack's proposal helped companies, he contacted university entrepreneurs for comments.

He contacted university founders.

Once he knew he'd correctly identified the problem and that people were willing to pay to address it, he started developing.

He earned $100k in a university entrepreneurship competition.

His plan was evident by then.

The other startup's founders saw his potential and granted him $400k to launch his own SaaS.

Hiring

He started looking for a tech co-founder because he lacked IT skills.

He interviewed dozens and picked the finest.

As he didn't want to wait for his program to be ready, he contacted hundreds of potential clients and got 15 letters of intent promising they'd join up when it was available.

YC accepted him by then.

He had enough positive signals to raise.

Raising

He didn't say how many VCs he called, but he indicated 50 were interested.

He jammed meetings into two weeks to generate pressure and encourage them to invest.

Seed raise: $11 million.

Selling

His objective was to contact as many entrepreneurs as possible to promote his product.

He first contacted startups by scraping CrunchBase data.

Once he had more money, he started targeting companies with ZoomInfo.

His VC urged him not to hire salespeople until he closed 50 clients himself.

He closed 100 and hired a CRO through a headhunter.

Scaling

Three persons started the business.

1. He primarily works in sales.

2. Coding the product was done by his co-founder.

3. Another person performing operational duties.

He regretted recruiting the third co-founder, who was ineffective (could have hired an employee instead).

He wanted his company to be big, so he hired two young marketing people from a competing company.

After validating several marketing channels, he chose PR.

$100 Million and under

He developed a sales team and now employs 30 individuals.

He raised a $100 million Series A.

Additionally, he stated

• He’s been rejected a lot. Like, a lot.

• Two great books to read: Steve Jobs by Isaacson, and Why Startups Fail by Tom Eisenmann.

• The best skill to learn for non-tech founders is “telling stories”, which means sales. A founder’s main job is to convince: co-founders, employees, investors, and customers. Learn code, or learn sales.

Conclusion

I often read about these stories but hardly take them seriously.

Zack was amazing.

Three things about him stand out:

1. His vision. He possessed a certain amount of fire.

2. His vitality. The man had a lot of enthusiasm and spoke quickly and decisively. He takes no chances and pushes the envelope in all he does.

3. His Rolex.

He didn't do all this in 18 months.

Not really.

He couldn't launch his company without private equity experience.

These accounts disregard entrepreneurs' original knowledge.

Hormozi will tell you how he founded Gym Launch, but he won't tell you how he had a gym first, how he worked at uni to pay for his gym, or how he went to the gym and learnt about fitness, which gave him the idea to open his own.

Nobody knows nothing. If you scale quickly, it's probable because you gained information early.

Lincoln said, "Give me six hours to chop down a tree, and I'll spend four sharpening the axe."

Sharper axes cut trees faster.

Could this happen?

Medium isn't like other social media giants. It wasn't a dot-com startup that became a multi-trillion-dollar social media firm. It launched in 2012 but didn't gain popularity until later. Now, it's one of the largest sites by web traffic, but it's still little compared to most. Most of Medium's traffic is external, but they don't run advertisements, so it's all about memberships.

Medium isn't profitable, but they don't disclose how terrible the problem is. Most of the $163 million they raised has been spent or used for acquisitions. If the money turns off, Medium can't stop paying its writers since the site dies. Writers must be paid, but they can't substantially slash payment without hurting the platform. The existing model needs scale to be viable and has a low ceiling. Facebook and other free social media platforms are struggling to retain users. Here, you must pay to appreciate it, and it's bad for writers AND readers. If I had the same Medium stats on YouTube, I'd make thousands of dollars a month.

Then what? Medium has tried to monetize by offering writers a cut of new members, but that's unsustainable. People-based growth is limited. Imagine recruiting non-Facebook users and getting them to pay to join. Some may, but I'd rather write.

Alternatives:

• Donation buttons

• Tiered subscriptions ($5, $10, $25, etc.)

• Expanding content

and these may be short-term fixes, but they're not as profitable as allowing ads. Advertisements can pay several dollars per click and cents every view. If you get 40,000 views a month like me, that's several thousand instead of a few hundred. Also, Medium would have enough money to split ad revenue with writers, who would make more. I'm among the top 6% of Medium writers. Only 6% of Medium writers make more than $100, and I made $500 with 35,000 views last month. Compared to YouTube, the top 1% of Medium authors make a lot. Mr. Beast and PewDiePie make MILLIONS a month, yet top Medium writers make tens of thousands. Sure, paying 3 or 4 people a few grand, or perhaps tens of thousands, will keep them around. What if great authors leveraged their following to go huge on YouTube and abandoned Medium? If people use Medium to get successful on other platforms, Medium will be continuously cycling through authors and paying them to stay.

Ads might make writing on Medium more profitable than making videos on YouTube because they could preserve the present freemium model and pay users based on internal views. The $5 might be ad-free.

Consider: Would you accept Medium ads? A $5 ad-free version + pay-as-you-go, etc. What are your thoughts on this?

Original post available here

Open to ideas or acquisitions

Failure is an unavoidable aspect of life, yet many recoil at the word.

I've worked on unrelated startup projects. This is a list of products I developed (often as the tech lead or co-founder) and why they failed to launch.

Chess Bet (Betting)

As a chess player who plays 5 games a day and has an ELO rating of 2100, I tried to design a chess engine to rival stockfish and Houdini.

While constructing my chess engine, my cofounder asked me about building a p2p chess betting app. Chess Bet. There couldn't be a better time.

Two people in different locations could play a staked game. The winner got 90% of the bet and we got 10%. The business strategy was clear, but our mini-launch was unusual.

People started employing the same cheat engines I mentioned, causing user churn and defaming our product.

It was the first programming problem I couldn't solve after building a cheat detection system based on player move strengths and prior games. Chess.com, the most famous online chess software, still suffers from this.

We decided to pivot because we needed an expensive betting license.

We relaunched as Chess MVP after deciding to focus on chess learning. A platform for teachers to create chess puzzles and teach content. Several chess students used our product, but the target market was too tiny.

We chose to quit rather than persevere or pivot.

BodaCare (Insure Tech)

‘BodaBoda’ in Swahili means Motorcycle. My Dad approached me in 2019 (when I was working for a health tech business) about establishing an Insurtech/fintech solution for motorbike riders to pay for insurance using SNPL.

We teamed up with an underwriter to market motorcycle insurance. Once they had enough premiums, they'd get an insurance sticker in the mail. We made it better by splitting the cover in two, making it more reasonable for motorcyclists struggling with lump-sum premiums.

Lack of capital and changing customer behavior forced us to close, with 100 motorcyclists paying 0.5 USD every day. Our unit econ didn't make sense, and CAC and retention capital only dug us deeper.

Circle (Social Networking)

Having learned from both product failures, I began to understand what worked and what didn't. While reading through Instagram, an idea struck me.

Suppose social media weren't virtual.

Imagine meeting someone on your way home. Like-minded person

People were excited about social occasions after covid restrictions were eased. Anything to escape. I just built a university student-popular experiences startup. Again, there couldn't be a better time.

I started the Android app. I launched it on Google Beta and oh my! 200 people joined in two days.

It works by signaling if people are in a given place and allowing users to IM in hopes of meeting up in near real-time. Playstore couldn't deploy the app despite its success in beta for unknown reasons. I appealed unsuccessfully.

My infrastructure quickly lost users because I lacked funding.

In conclusion

This essay contains many failures, some of which might have been avoided and others not, but they were crucial learning points in my startup path.

If you liked any idea, I have the source code on Github.

Happy reading until then!

For some people, the glass is half empty. For others, it’s half full. And for some, the question is, How do I get this glass totally full again?

Problem-solvers are the last group. They're neutral. Pragmatists.

Problems surround them. They fix things instead of judging them. Problem-solvers improve the world wherever they go.

Some fail. Sometimes their good intentions have terrible results. Like when they try to help a grandma cross the road because she can't do it alone but discover she never wanted to.

Most programmers, software engineers, and data scientists solve problems. They use computer code to fix problems they see.

Coding is best done by understanding and solving the problem.

Despite your best intentions, building the wrong solution may have negative consequences. Helping an unwilling grandma cross the road.

How can you improve problem-solving?

1. Examine your presumptions.

Don’t think There’s a grandma, and she’s unable to cross the road. Therefore I must help her over the road. Instead think This grandma looks unable to cross the road. Let’s ask her whether she needs my help to cross it.

Maybe the grandma can’t cross the road alone, but maybe she can. You can’t tell for sure just by looking at her. It’s better to ask.

Maybe the grandma wants to cross the road. But maybe she doesn’t. It’s better to ask!

Building software is similar. Do only I find this website ugly? Who can I consult?

We all have biases, mental shortcuts, and worldviews. They simplify life.

Problem-solving requires questioning all assumptions. They might be wrong!

Think less. Ask more.

Secondly, fully comprehend the issue.

Grandma wants to cross the road? Does she want flowers from the shop across the street?

Understanding the problem advances us two steps. Instead of just watching people and their challenges, try to read their intentions.

Don't ask, How can I help grandma cross the road? Why would this grandma cross the road? What's her goal?

Understand what people want before proposing solutions.

3. Request more information. This is not a scam!

People think great problem solvers solve problems immediately. False!

Problem-solvers study problems. Understanding the problem makes solving it easy.

When you see a grandma struggling to cross the road, you want to grab her elbow and pull her over. However, a good problem solver would ask grandma what she wants. So:

Problem solver: Excuse me, ma’am? Do you wish to get over the road? Grandma: Yes indeed, young man! Thanks for asking. Problem solver: What do you want to do on the other side? Grandma: I want to buy a bouquet of flowers for my dear husband. He loves flowers! I wish the shop wasn’t across this busy road… Problem solver: Which flowers does your husband like best? Grandma: He loves red dahlia. I usually buy about 20 of them. They look so pretty in his vase at the window! Problem solver: I can get those dahlia for you quickly. Go sit on the bench over here while you’re waiting; I’ll be back in five minutes. Grandma: You would do that for me? What a generous young man you are!

A mediocre problem solver would have helped the grandma cross the road, but he might have forgotten that she needs to cross again. She must watch out for cars and protect her flowers on the way back.

A good problem solver realizes that grandma's husband wants 20 red dahlias and completes the task.

4- Rapid and intense brainstorming

Understanding a problem makes solutions easy. However, you may not have all the information needed to solve the problem.

Additionally, retrieving crucial information can be difficult.

You could start a blog. You don't know your readers' interests. You can't ask readers because you don't know who they are.

Brainstorming works here. Set a stopwatch (most smartphones have one) to ring after five minutes. In the remaining time, write down as many topics as possible.

No answer is wrong. Note everything.

Sort these topics later. Programming or data science? What might readers scroll past—are these your socks this morning?

Rank your ideas intuitively and logically. Write Medium stories using the top 35 ideas.

5 - Google it.

Doctor Google may answer this seemingly insignificant question. If you understand your problem, try googling or binging.

Someone has probably had your problem before. The problem-solver may have posted their solution online.

Use others' experiences. If you're social, ask a friend or coworker for help.

6 - Consider it later

Rest your brain.

Reread. Your brain needs rest to function.

Hustle culture encourages working 24/7. It doesn't take a neuroscientist to see that this is mental torture.

Leave an unsolvable problem. Visit friends, take a hot shower, or do whatever you enjoy outside of problem-solving.

Nap.

I get my best ideas in the morning after working on a problem. I couldn't have had these ideas last night.

Sleeping subconsciously. Leave it alone and you may be surprised by the genius it produces.

7 - Learn to live with frustration

There are problems that you’ll never solve.

Mathematicians are world-class problem-solvers. The brightest minds in history have failed to solve many mathematical problems.

A Gordian knot problem can frustrate you. You're smart!

Frustration-haters don't solve problems well. They choose simple problems to avoid frustration.

No. Great problem solvers want to solve a problem but know when to give up.

Frustration initially hurts. You adapt.

Famous last words

If you read this article, you probably solve problems. We've covered many ways to improve, so here's a summary:

1. Test your presumptions. Is the issue the same for everyone else when you see one? Or are your prejudices and self-judgments misguiding you?

2. Recognize the issue completely. On the surface, a problem may seem straightforward, but what's really going on? Try to see what the current situation might be building up to by thinking two steps ahead of the current situation.

3. Request more information. You are no longer a high school student. A two-sentence problem statement is not sufficient to provide a solution. Ask away if you need more details!

4. Think quickly and thoroughly. In a constrained amount of time, try to write down all your thoughts. All concepts are worthwhile! Later, you can order them.

5. Google it. There is a purpose for the internet. Use it.

6. Consider it later at night. A rested mind is more creative. It might seem counterintuitive to leave a problem unresolved. But while you're sleeping, your subconscious will handle the laborious tasks.

7. Accept annoyance as a normal part of life. Don't give up if you're feeling frustrated. It's a step in the procedure. It's also perfectly acceptable to give up on a problem because there are other, more pressing issues that need to be addressed.

You might feel stupid sometimes, but that just shows that you’re human. You care about the world and you want to make it better.

At the end of the day, that’s all there is to problem solving — making the world a little bit better.

Understanding your own energy depletion and restoration is how to truly optimize

Hack has meant many bad things for centuries. In the 1800s, a hack was a meager horse used to transport goods.

Modern usage describes a butcher or ax murderer's cleaver chop. The 1980s programming boom distinguished elegant code from "hacks". Both got you to your goal, but the latter made any programmer cringe and mutter about changing the code. From this emerged the hacker trope, the friendless anti-villain living in a murky hovel lit by the computer monitor, eating junk food and breaking into databases to highlight security system failures or steal hotdog money.

Now, start-a-billion-dollar-business-from-your-garage types have shifted their sights from app development to DIY biology, coining the term "bio-hack". This is a required keyword and meta tag for every fitness-related podcast, book, conference, app, or device.

Bio-hacking involves bypassing your body and mind's security systems to achieve a goal. Many biohackers' initial goals were reasonable, like lowering blood pressure and weight. Encouraged by their own progress, self-determination, and seemingly exquisite control of their biology, they aimed to outsmart aging and death to live 180 to 1000 years (summarized well in this vox.com article).

With this grandiose north star, the hunt for novel supplements and genetic engineering began.

Companies selling do-it-yourself biological manipulations cite lab studies in mice as proof of their safety and success in reversing age-related diseases or promoting longevity in humans (the goal changes depending on whether a company is talking to the federal government or private donors).

The FDA is slower than science, they say. Why not alter your biochemistry by buying pills online, editing your DNA with a CRISPR kit, or using a sauna delivered to your home? How about a microchip or electrical stimulator?

What could go wrong?

I'm not the neo-police, making citizen's arrests every time someone introduces a new plumbing gadget or extrapolates from animal research on resveratrol or catechins that we should drink more red wine or eat more chocolate. As a scientist who's spent her career asking, "Can we get better?" I've come to view bio-hacking as misguided, profit-driven, and counterproductive to its followers' goals.

We're creatures of nature. Despite all the new gadgets and bio-hacks, we still use Roman plumbing technology, and the best way to stay fit, sharp, and happy is to follow a recipe passed down since the beginning of time. Bacteria, plants, and all natural beings are rhythmic, with alternating periods of high activity and dormancy, whether measured in seconds, hours, days, or seasons. Nature repeats successful patterns.

During the Upstate, every cell in your body is naturally primed and pumped full of glycogen and ATP (your cells' energy currencies), as well as cortisol, which supports your muscles, heart, metabolism, cognitive prowess, emotional regulation, and general "get 'er done" attitude. This big energy release depletes your batteries and requires the Downstate, when your subsystems recharge at the cellular level.

Downstates are when you give your heart a break from pumping nutrient-rich blood through your body; when you give your metabolism a break from inflammation, oxidative stress, and sympathetic arousal caused by eating fast food — or just eating too fast; or when you give your mind a chance to wander, think bigger thoughts, and come up with new creative solutions. When you're responding to notifications, emails, and fires, you can't relax.

Downstates aren't just for consistently recharging your battery. By spending time in the Downstate, your body and brain get extra energy and nutrients, allowing you to grow smarter, faster, stronger, and more self-regulated. This state supports half-marathon training, exam prep, and mediation. As we age, spending more time in the Downstate is key to mental and physical health, well-being, and longevity.

When you prioritize energy-demanding activities during Upstate periods and energy-replenishing activities during Downstate periods, all your subsystems, including cardiovascular, metabolic, muscular, cognitive, and emotional, hum along at their optimal settings. When you synchronize the Upstates and Downstates of these individual rhythms, their functioning improves. A hard workout causes autonomic stress, which triggers Downstate recovery.

By choosing the right timing and type of exercise during the day, you can ensure a deeper recovery and greater readiness for the next workout by working with your natural rhythms and strengthening your autonomic and sleep Downstates.

Morning cardio workouts increase deep sleep compared to afternoon workouts. Timing and type of meals determine when your sleep hormone melatonin is released, ushering in sleep.

Rhythm isn't a hack. It's not a way to cheat the system or the boss. Nature has honed its optimization wisdom over trillions of days and nights. Stop looking for quick fixes. You're a whole system made of smaller subsystems that must work together to function well. No one pill or subsystem will make it all work. Understanding and coordinating your rhythms is free, easy, and only benefits you.

Dr. Sara C. Mednick is a cognitive neuroscientist at UC Irvine and author of The Power of the Downstate (HachetteGO)