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.

Here's the fastest way to validate company concepts.

I squandered a year after dropping out of Stanford designing a product nobody wanted.

But today, I’m at 100k!

Differences:

I was designing a consumer product when I dropped out.

I coded MVP, got 1k users, and got YC interview.

Nice, huh?

WRONG!

Still coding and getting users 12 months later

WOULD PEOPLE PAY FOR IT? was the riskiest assumption I hadn't tested.

When asked why I didn't verify payment, I said,

Not-ready products. Now, nobody cares. The website needs work. Include this. Increase usage…

I feared people would say no.

After 1 year of pushing it off, my team told me they were really worried about the Business Model. Then I asked my audience if they'd buy my product.

So?

No, overwhelmingly.

I felt like I wasted a year building a product no one would buy.

Founders Cafe was the opposite.

Before building anything, I requested payment.

40 founders were interviewed.

Then we emailed Stanford, YC, and other top founders, asking them to join our community.

BOOM! 10/12 paid!

Without building anything, in 1 day I validated my startup's riskiest assumption. NOT 1 year.

Asking people to pay is one of the scariest things.

I understand.

I asked Stanford queer women to pay before joining my gay sorority.

I was afraid I'd turn them off or no one would pay.

Gay women, like those founders, were in such excruciating pain that they were willing to pay me upfront to help.

You can ask for payment (before you build) to see if people have the burning pain. Then they'll pay!

Examples from Founders Cafe members:

😮 Using a fake landing page, a college dropout tested a product. Paying! He built it and made $3m!

😮 YC solo founder faked a Powerpoint demo. 5 Enterprise paid LOIs. $1.5m raised, built, and in YC!

😮 A Harvard founder can convert Figma to React. 1 day, 10 customers. Built a tool to automate Figma -> React after manually fulfilling requests. 1m+

Bad example:

😭 Stanford Dropout Spends 1 Year Building Product Without Payment Validation

Some people build for a year and then get paying customers.

What I'm sharing is my experience and what Founders Cafe members have told me about validating startup ideas.

Don't waste a year like I did.

After my first startup failed, I planned to re-enroll at Stanford/work at Facebook.

After people paid, I quit for good.

I've hit $100k!

Hope this inspires you to request upfront payment! It'll change your life

What they'll do is scarier.

My acquaintance recently joined a VC-funded startup. Money, equity, and upside possibilities were nice, but he had a nagging dread.

They just secured a $40M round and are hiring like crazy to prepare for their IPO in two years. All signals pointed to this startup's (a B2B IT business in a stable industry) success, and its equity-holding workers wouldn't pass that up.

Five months after starting the work, my friend struggled with leaving. We might overlook the awful culture and long hours at the proper price. This price plus the company's fate and survival abilities sent my friend departing in an unpleasant unplanned resignation before jumping on yet another sinking ship.

This affects founders. This affects VC-backed companies (and all businesses). This affects anyone starting, buying, or running a business.

Here's the under-the-table approach that's draining VC capital, leaving staff terrified (or jobless), founders rattled, and investors upset. How to recognize, solve, and avoid it

The unsettling reality behind door #1

You can't raise money off just your looks, right? If "looks" means your founding team's expertise, then maybe. In my friend's case, the founding team's strong qualifications and track records won over investors before talking figures.

They're hardly the only startup to raise money without a profitable customer acquisition strategy. Another firm raised money for an expensive sleep product because it's eco-friendly. They were off to the races with a few keywords and key players.

Both companies, along with numerous others, elected to invest on product development first. Company A employed all the tech, then courted half their market (they’re a tech marketplace that connects two parties). Company B spent millions on R&D to create a palatable product, then flooded the world with marketing.

My friend is on Company B's financial team, and he's seen where they've gone wrong. It's terrible.

Company A (tech market): Growing? Not quite. To achieve the ambitious expansion they (and their investors) demand, they've poured much of their little capital into salespeople: Cold-calling commission and salary salesmen. Is it working? Considering attrition and companies' dwindling capital, I don't think so.

Company B (green sleep) has been hiring, digital marketing, and opening new stores like crazy. Growing expenses should result in growing revenues and a favorable return on investment; if you grow too rapidly, you may neglect to check that ROI.

Once Company A cut headcount and Company B declared “going concerned”, my friend realized both startups had the same ailment and didn't recognize it.

I shouldn't have to ask a friend to verify a company's cash reserves and profitability to spot a financial problem. It happened anyhow.

The frightening part isn't that investors were willing to invest millions without product-market fit, CAC, or LTV estimates. That's alarming, but not as scary as the fact that startups aren't understanding the problem until VC rounds have dried up.

When they question consultants if their company will be around in 6 months. It’s a red flag. How will they stretch $20M through a 2-year recession with a $3M/month burn rate and no profitability? Alarms go off.

Who's in danger?

In a word, everyone who raised money without a profitable client acquisition strategy or enough resources to ride out dry spells.

Money mismanagement and poor priorities affect every industry (like sinking all your capital into your product, team, or tech, at the expense of probing what customer acquisition really takes and looks like).

This isn't about tech, real estate, or recession-proof luxury products. Fast, cheap, easy money flows into flashy-looking teams with buzzwords, trending industries, and attractive credentials.

If these companies can't show progress or get a profitable CAC, they can't raise more money. They die if they can't raise more money (or slash headcount and find shoestring budget solutions until they solve the real problem).

The kiss of death (and how to avoid it)

If you're running a startup and think raising VC is the answer, pause and evaluate. Do you need the money now?

I'm not saying VC is terrible or has no role. Founders have used it as a Band-Aid for larger, pervasive problems. Venture cash isn't a crutch for recruiting consumers profitably; it's rocket fuel to get you what and who you need.

Pay-to-play isn't a way to throw money at the wall and hope for a return. Pay-to-play works until you run out of money, and if you haven't mastered client acquisition, your cash will diminish quickly.

How can you avoid this bottomless pit? Tips:

• Understand your burn rate

• Keep an eye on your growth or profitability.

• Analyze each and every marketing channel and initiative.

• Make lucrative customer acquisition strategies and satisfied customers your top two priorities. not brand-new products. not stellar hires. avoid the fundraising rollercoaster to save time. If you succeed in these two tasks, investors will approach you with their thirsty offers rather than the other way around, and your cash reserves won't diminish as a result.

Not as much as your grandfather

My family friend always justified expensive, impractical expenditures by saying it was only monopoly money. In business, startups, and especially with money from investors expecting a return, that's not true.

More founders could understand that there isn't always another round if they viewed VC money as their own limited pool. When the well runs dry, you must refill it or save the day.

Venture financing isn't your grandpa's money. A discerning investor has entrusted you with dry powder in the hope that you'll use it wisely, strategically, and thoughtfully. Use it well.

Apple's latest revelation may shock iPod fans and former owners.

Apple discontinued the iPod touch on May 11, 2022. After 21 years, Apple killed the last surviving iPod, a device Steve Jobs believed would revolutionize the music industry.

Jobs was used to making bold predictions, but few expected Apple's digital music player to change the music industry. It did.

This chaos created new business opportunities. Spotify, YouTube, and Amazon are products of that chaotic era.

As the digital landscape changes, so do consumers, and the iPod has lost favor. I'm sure Apple realizes the importance of removing an icon. The iPod was Apple like the Mac and iPhone. I think it's bold to retire such a key Apple cornerstone. What would Jobs do?

iPod evolution across the ages

Here's an iPod family tree for all you enthusiasts.

iPod vintage (Oct 2001 to Sep 2014, 6 generations)

The original iPod had six significant upgrades since 2001. Apple announced an 80 GB ($249) and 160 GB ($349) iPod classic in 2007.

Apple updated the 80 GB model with a 120 GB device in September 2008. Apple upgraded the 120 GB model with a 160 GB variant a year later (2009). This was the last iteration, and Apple discontinued the classic in September 2014.

iPod nano (Jan 2004 to Sep 2005, 2 generations)

Apple debuted a smaller, brightly-colored iPod in 2004. The first model featured 4 GB, enough for 1,000 songs.

Apple produced a new 4 GB or 6 GB iPod mini in February 2005 and discontinued it in September when they released a better-looking iPod nano.

iTouch nano (Sep 2005 to July 2017, 7 generations)

I loved the iPod nano. It was tiny and elegant with enough tech to please most music aficionados, unless you carry around your complete music collection.

Apple owed much of the iPod nano's small form and success to solid-state flash memory. Flash memory doesn't need power because it has no moving parts. This makes the iPod nano more durable than the iPod classic and mini, which employ hard drives.

Apple manufactured seven generations of the iPod nano, improving its design, display screen, memory, battery, and software, but abandoned it in July 2017 due to dwindling demand.

Shuffle iPod (Jan 2005 to Jul 2017, 4 generations)

The iPod shuffle was entry-level. It was a simple, lightweight, tiny music player. The iPod shuffle was perfect for lengthy bike trips, runs, and hikes.

Apple sold 10 million iPod shuffles in the first year and kept making them for 12 years, through four significant modifications.

iOS device (Sep 2007 to May 2022, 7 generations)

The iPod touch's bigger touchscreen interface made it a curious addition to the iPod family. The iPod touch resembled an iPhone more than the other iPods, making them hard to tell apart.

Many were dissatisfied that Apple removed functionality from the iPod touch to avoid making it too similar to the iPhone. Seven design improvements over 15 years brought the iPod touch closer to the iPhone, but not completely.

The iPod touch uses the same iOS operating system as the iPhone, giving it access to many apps, including handheld games.

The iPod touch's long production run is due to the next generation of music-loving gamers.

What made the iPod cool

iPod revolutionized music listening. It was the first device to store and play MP3 music, allowing you to carry over 1,000 songs anywhere.

The iPod changed consumer electronics with its scroll wheel and touchscreen. Jobs valued form and function equally. He showed people that a product must look good to inspire an emotional response and ignite passion.

The elegant, tiny iPod was a tremendous sensation when it arrived for $399 in October 2001. Even at this price, it became a must-have for teens to CEOs.

It's hard to identify any technology that changed how music was downloaded and played like the iPod. Apple iPod and iTunes had 63% of the paid music download market in the fourth quarter of 2012.

The demise of the iPod was inevitable

Apple discontinuing the iPod touch after 21 years is sad. This ends a 00s music icon.

Jobs was a genius at anticipating market needs and opportunities, and Apple launched the iPod at the correct time.

Few consumer electronics items have had such a lasting impact on music lovers and the music industry as the iPod.

Smartphones and social media have contributed to the iPod's decline. Instead of moving to the music, the new generation of consumers is focused on social media. They're no longer passive content consumers; they're active content creators seeking likes and followers. Here, the smartphone has replaced the iPod.

It's hard not to feel a feeling of loss, another part of my adolescence now forgotten by the following generation.

So, if you’re lucky enough to have a working iPod, hang on to that relic and enjoy the music and the nostalgia.