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.

This is for young entrepreneurs, especially in tech.

People give useless success advice on TikTok and Reddit. Early risers, bookworms, etc. Entrepreneurship courses. Work hard and hustle.

False. These aren't successful traits.

I mean, organization is good. As someone who founded several businesses and now works at a VC firm, I find these tips to be clichés.

Based on founding four successful businesses and working with other successful firms, here's my best actionable advice:

1. Choose a sector or a niche and become an expert in it.

This is more generic than my next tip, but it's a must-do that's often overlooked. Become an expert in the industry or niche you want to enter. Discover everything.

Buy (future) competitors' products. Understand consumers' pain points. Market-test. Target keyword combos. Learn technical details.

The most successful businesses I've worked with were all formed by 9-5 employees. They knew the industry's pain points. They started a business targeting these pain points.

2. Choose a niche or industry crossroads to target.

How do you choose an industry or niche? What if your industry is too competitive?

List your skills and hobbies. Randomness is fine. Find an intersection between two interests or skills.

Say you build websites well. You like cars.

Web design is a *very* competitive industry. Cars and web design?

Instead of web design, target car dealers and mechanics. Build a few fake demo auto mechanic websites, then cold call shops with poor websites. Verticalize.

I've noticed a pattern:

• Person works in a particular industry for a corporation.

• Person gains expertise in the relevant industry.

• Person quits their job and launches a small business to address a problem that their former employer was unwilling to address.

I originally posted this on Reddit and it seemed to have taken off so I decided to share it with you all.

Focus on the product. When someone buys from you, you convince them the product's value exceeds the price. It's not fair and favors the buyer.

Creating a superior product or service will win. Narrowing this helps you outcompete others.

You may be their only (lucky) option.

Startup entrepreneurs assume what risks when pitching?

Last week I signed four NDAs.

Four!

NDA stands for non-disclosure agreement. A legal document given to someone receiving confidential information. By signing, the person pledges not to share the information for a certain time. If they do, they may be in breach of contract and face legal action.

Companies use NDAs to protect trade secrets and confidential internal information from employees and contractors. Appropriate. If you manage a huge, successful firm, you don't want your employees selling their information to your competitors. To be true, business NDAs don't always prevent corporate espionage, but they usually make employees and contractors think twice before sharing.

I understand employee and contractor NDAs, but I wasn't asked to sign one. I counsel entrepreneurs, thus the NDAs I signed last week were from startups that wanted my feedback on their concepts.

I’m not a startup investor. I give startup guidance online. Despite that, four entrepreneurs thought their company ideas were so important they wanted me to sign a generically written legal form they probably acquired from a shady, spam-filled legal templates website before we could chat.

False. One company tried to get me to sign their NDA a few days after our conversation. I gently rejected, but their tenacity encouraged me. I considered sending retroactive NDAs to everyone I've ever talked to about one of my startups in case they establish a successful company based on something I said.

Two of the other three NDAs were from nearly identical companies. Good thing I didn't sign an NDA for the first one, else they may have sued me for talking to the second one as though I control the firms people pitch me.

I wasn't talking to the fourth NDA company. Instead, I received an unsolicited email from someone who wanted comments on their fundraising pitch deck but required me to sign an NDA before sending it.

That's right, before I could read a random Internet stranger's unsolicited pitch deck, I had to sign his NDA, potentially limiting my ability to discuss what was in it.

You should understand. Advisors, mentors, investors, etc. talk to hundreds of businesses each year. They cannot manage all the companies they deal with, thus they cannot risk legal trouble by talking to someone. Well, if I signed NDAs for all the startups I spoke with, half of the 300+ articles I've written on Medium over the past several years could get me sued into the next century because I've undoubtedly addressed topics in my articles that I discussed with them.

The four NDAs I received last week are part of a recent trend of entrepreneurs sending out NDAs before meetings, despite the practical and legal issues. They act like asking someone to sign away their right to talk about all they see and hear in a day is as straightforward as asking for a glass of water.

Given this inflow of NDAs, I wanted to briefly remind entrepreneurs reading this blog about the merits and cons of requesting investors (or others in the startup ecosystem) to sign your NDA.

Benefits of having investors sign your NDA include:

None. Zero. Nothing.

Disadvantages of requesting investor NDAs:

• You'll come off as an amateur who has no idea what it takes to launch a successful firm.

• Investors won't trust you with their money since you appear to be a complete amateur.

• Printing NDAs will be a waste of paper because no genuine entrepreneur will ever sign one.

I apologize for missing any cons. Please leave your remarks.

And morning water bottle struggles.

Welcome to my TikTok, where I share my stay-at-home life! I'll show you my usual day from morning to night.

I rise early to prepare my guy iced coffee. I make matcha, my favorite drink. I also fill our water bottles, which takes time and effort, so I record and describe the procedure. As you see me perform the unthinkable by putting a water bottle in a soda machine, you'll see my magnificent but unowned condo. My lover has everything, including:

1. In the living room, a sizable velvet alabaster divan. I was unable to use the words white or sofa in place of alabaster or a divan since they are insufficiently elegant and do not adequately convey how opulent the item is. The price tag on the divan was another huge feature; I'm sure my lover wouldn't purchase any furniture for less than $20k because it would be beneath him.

2. A plush Swiss coffee-colored Tabriz carpet. Once more, white is a color associated with the underclass; for us, the wealthy, it's alabaster or swiss coffee. Sorry, my boyfriend is wealthy; I'm truly in the same situation. And yet, I’m the one whos freeloading off of him, not you haha!

3. Soft translucent powder is the hue of the vinyl wallcoverings. I merely made up the name of that hue, but I have to maintain the online character I've established. There is no room for adopting language typical of peasant people; I must reiterate that I am wealthy while they are not.

I rest after filling our water bottles. I'm really fatigued from chores. My boyfriend is skeptical about hiring a housekeeper and cook. Does he assume I'm a servant or maid? I can't be overly demanding or throw a tantrum since he may replace me with a younger version. Leonardo Di Caprio's fault!

After the break, I bring my lover a water bottle. He's off to work with my best wishes. After cleaning the shower, I text my BF saying I broke a nail. He charged $675 for a crystal-topped shellac manicure. Lucky me!

After this morning's crazy choirs, especially the water bottle one, I'm famished. I dress quickly and go to the neighborhood organic-vegan-gluten-free-sugar-free-plasma-free-GMO-free-HBO-free breakfast place. Most folks can't afford $17.99 for a caffeine-free-mushroom-plus-mud-and-electrolytes morning beverage. It goes nicely with my matcha. Eggs Benedict cost $68. English muffins are off-limits. I can't make myself obese. My partner said he'd swap me for a 19-year-old Eastern European if I keep eating bacon.

I leave no tip since tipping is too much pressure and math for me, so I go shopping.

My shopping adventures have gotten monotonous. 47 designer bags and 114 bag covers Birkins need their own luggage. My babies! I've never caught my BF with a baby. I have sleeping medications and a turkey baster. Tatiana is much younger and thinner than me, so I can't lose him to her. The goal is to become a stay-at-home wife shortly. A turkey baster is essential.

After spending $955 on La Mer lotions and getting a crystal manicure, I nap. Before my boyfriend's return, I can nap for 5 hours.

I wake up around 4 pm — it’s time to prepare dinner. Yes, I said “prepare for dinner,” not “prepare dinner.” I have crystals on my nails! Do you really think I would cook? No way.

My husband's arrival still requires much work. I clean the kitchen, get cutlery and napkins. I order UberEats while my BF is 30-45 minutes away.

Wagyu steaks with Matsutake mushroom soup today. I pick desserts for my lover but not myself. Eastern European threat?

When my BF gets home from work, we eat. I don't believe in tipping UberEats drivers. If he wants to appreciate life's finer things, he should locate a rich woman.

After eating, we plan our getaway. I requested Aruba's fanciest hotel for winter and expect a butler. We're bickering over who gets the butler. We may need two.

Day's end, I'm exhausted. Stay-at-home girlfriends put in a lot of time and work. Work and duties are never-ending.

Before bed, I shower and use a liquid gold mask in my 27-step makeup procedure. It's a French luxury brand, not La Mer.

Here's my day.

Note: I like satire and absurd trends. Stay-at-home-girlfriend TikTok videos have become popular recently.

I don't shame or support such agreements; I'm just an observer. Thanks for reading.

Reddit's NFT market is alive and well.

NFT owners outnumber OpenSea on Reddit.

Reddit NFTs flip in OpenSea in days:

Fast-selling.

NFT sales will make Reddit's current communities more engaged.

I don't think NFTs will affect existing groups, but they will build hype for people to acquire them.

The first season of Collectibles is unique, but many missed the first season.

Second-season NFTs are less likely to be sold for a higher price than first-season ones.

If you use Reddit, it's fun to own NFTs.

I've been pondering product strategy and how to articulate it. Frameworks helped guide our thinking.

If your teams aren't working together or there's no clear path to victory, your product strategy may not be well-articulated or communicated (if you have one).

Before diving into a product strategy's details, it's important to understand its role in the bigger picture — the pieces that move your organization forward.

the overall picture

A product strategy is crucial, in my opinion. It's part of a successful product or business. It's the showpiece.

To simplify, we'll discuss four main components:

1. Vision

2. Product Management

3. Goals

4. Roadmap

Vision

Your company's mission? Your company/product in 35 years? Which headlines?

The vision defines everything your organization will do in the long term. It shows how your company impacted the world. It's your organization's rallying cry.

An ambitious but realistic vision is needed.

Without a clear vision, your product strategy may be inconsistent.

Product Management

Our main subject. Product strategy connects everything. It fulfills the vision.

In Part 2, we'll discuss product strategy.

Goals

This component can be goals, objectives, key results, targets, milestones, or whatever goal-tracking framework works best for your organization.

These product strategy metrics will help your team prioritize strategies and roadmaps.

Your company's goals should be unified. This fuels success.

Roadmap

The roadmap is your product strategy's timeline. It provides a prioritized view of your team's upcoming deliverables.

A roadmap is time-bound and includes measurable goals for your company. Your team's steps and capabilities for executing product strategy.

If your team has trouble prioritizing or defining a roadmap, your product strategy or vision is likely unclear.

Formulation of a Product Strategy

Now that we've discussed where your product strategy fits in the big picture, let's look at a framework.

A product strategy should include challenges, an approach, and actions.

Challenges

First, analyze the problems/situations you're solving. It can be customer- or company-focused.

The analysis should explain the problems and why they're important. Try to simplify the situation and identify critical aspects.

Some questions:

• What issues are we attempting to resolve?

• What obstacles—internal or otherwise—are we attempting to overcome?

• What is the opportunity, and why should we pursue it, in your opinion?

Decided Method

Second, describe your approach. This can be a set of company policies for handling the challenge. It's the overall approach to the first part's analysis.

The approach can be your company's bets, the solutions you've found, or how you'll solve the problems you've identified.

Again, these questions can help:

• What is the value that we hope to offer to our clients?

• Which market are we focusing on first?

• What makes us stand out? Our benefit over rivals?

Actions

Third, identify actions that result from your approach. Second-part actions should be these.

Coordinate these actions. You may need to add products or features to your roadmap, acquire new capabilities through partnerships, or launch new marketing campaigns. Whatever fits your challenges and strategy.

Final questions:

• What skills do we need to develop or obtain?

• What is the chosen remedy? What are the main outputs?

• What else ought to be added to our road map?

Put everything together

… and iterate!

Strategy isn't one-and-done. Changes occur. Economies change. Competitors emerge. Customer expectations change.

One unexpected event can make strategies obsolete quickly. Muscle it. Review, evaluate, and course-correct your strategies with your teams. Quarterly works. In a new or unstable industry, more often.