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.

We love round numbers, don't we? $100,000 is a frequent freelancing milestone. You feel like six figures means you're doing something properly.

You've most likely already conquered initial freelancing challenges like finding clients, setting fair pricing, coping with criticism, getting through dry spells, managing funds, etc.

You think I must be doing well. Last month, my freelance income topped $100,000.

That may not sound impressive considering I've been freelancing for 2.75 years, but I made 30% of that in the previous four months, which is crazy.

Here are the things I wish I'd known during the early days of self-employment that would have helped me hit $100,000 faster.

1. The Volatility of Freelancing Will Stabilize.

Freelancing is risky. No surprise.

Here's an example.

October 2020 was my best month, earning $7,150. Between $4,004 in September and $1,730 in November. Unsteady.

Freelancing is regrettably like that. Moving clients. Content requirements change. Allocating so much time to personal pursuits wasn't smart, but yet.

Stabilizing income takes time. Consider my rolling three-month average income since I started freelancing. My three-month average monthly income. In February, this metric topped $5,000. Now, it's in the mid-$7,000s, but it took a while to get there.

Finding freelance gigs that provide high pay, high volume, and recurring revenue is difficult. But it's not impossible.

TLDR: Don't expect a steady income increase at first. Be patient.

2. You Have More Value Than You Realize.

Writing is difficult. Assembling words, communicating a message, and provoking action are a puzzle.

People are willing to pay you for it because they can't do what you do or don't have enough time.

Keeping that in mind can have huge commercial repercussions.

When talking to clients, don't tiptoe. You can ignore ridiculous deadlines. You don't have to take unmanageable work.

You solve an issue, so make sure you get rightly paid.

TLDR: Frame services as problem-solutions. This will let you charge more and set boundaries.

3. Increase Your Prices.

I studied hard before freelancing. I read articles and watched videos about writing businesses.

I didn't want to work for pennies. Despite this clarity, I had no real strategy to raise my rates.

I then luckily stumbled into higher-paying work. We discussed fees and hours with a friend who launched a consulting business. It's subjective and speculative because value isn't standardized. One company may laugh at your charges. If your solution helps them create a solid ROI, another client may pay $200 per hour.

When he told me he charged his first client $125 per hour, I thought, Why not?

A new-ish client wanted to discuss a huge forthcoming project, so I raised my rates. They knew my worth, so they didn't blink when I handed them my new number.

TLDR: Increase rates periodically (e.g., every 6 or 12 months). Writing skill develops with practice. You'll gain value over time.

4. Remember Your Limits.

If you can squeeze additional time into a day, let me know. I can't manipulate time yet.

We all have time and economic limits. You could theoretically keep boosting rates, but your prospect pool diminishes. Outsourcing and establishing extra revenue sources might boost monthly revenues.

I've devoted a lot of time to side projects (hopefully extra cash sources), but I've only just started outsourcing. I wish I'd tried this earlier.

If you can discover good freelancers, you can grow your firm without sacrificing time.

TLDR: Expand your writing network immediately. You'll meet freelancers who understand your daily grind and locate reference sources.

5. Every Action You Take Involves an Investment. Be Certain to Select Correctly.

Investing in stocks or crypto requires paying money, right?

In business, time is your currency (and maybe money too). Your daily habits define your future. If you spend time collecting software customers and compiling content in the space, you'll end up with both. So be sure.

I only spend around 50% of my time on client work, therefore it's taken me nearly three years to earn $100,000. I spend the remainder of my time on personal projects including a freelance book, an investment newsletter, and this blog.

Why? I don't want to rely on client work forever. So, I'm working on projects that could pay off later and help me live a more fulfilling life.

TLDR: Consider the long-term impact of your time commitments, and don't overextend. You can only make so many "investments" in a given time.

6. LinkedIn Is an Endless Mine of Gold. Use It.

Why didn't I use LinkedIn earlier?

I designed a LinkedIn inbound lead strategy that generates 12 leads a month and a few high-quality offers. As a result, I've turned down good gigs. Wish I'd begun earlier.

If you want to create a freelance business, prioritize LinkedIn. Too many freelancers ignore this site, missing out on high-paying clients. Build your profile, post often, and interact.

TLDR: Study LinkedIn's top creators. Once you understand their audiences, start posting and participating daily.

For 99% of People, Freelancing is Not a Get-Rich-Quick Scheme.

Here's a list of things I wish I'd known when I started freelancing.

1. Although it is erratic, freelancing eventually becomes stable.

2. You deserve respect and discretion over how you conduct business because you have solved an issue.

3. Increase your charges rather than undervaluing yourself. If necessary, add a reminder to your calendar. Your worth grows with time.

4. In order to grow your firm, outsource jobs. After that, you can work on the things that are most important to you.

5. Take into account how your present time commitments may affect the future. It will assist in putting things into perspective and determining whether what you are doing is indeed worthwhile.

6. Participate on LinkedIn. You'll get better jobs as a result.

If I could give my old self (and other freelancers) one bit of advice, it's this:

Despite appearances, you're making progress.

Each job. Tweets. Newsletters. Progress. It's simpler to see retroactively than in the moment.

Consistent, intentional work pays off. No good comes from doing nothing. You must set goals, divide them into time-based targets, and then optimize your calendar.

Then you'll understand you're doing well.

Want to learn more? I’ll teach you.

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.

This is how to build a car while driving.

Building a high-growth startup is compared to building a car while it's speeding down the highway.

How to plan without going crazy? Or, without losing team, board, and investor buy-in?

I just delivered our company's product roadmap for the rest of the year. Complete. Thorough. Page-long. I'm optimistic about its chances of surviving as everything around us changes, from internal priorities to the global economy.

It's tricky. This isn't the first time I've created a startup roadmap. I didn't invent a document. It took time to deliver a document that will be relevant for months.

Goals matter.

Although they never change, goals are rarely understood.

This is the third in a series about a startup's unique roadmapping needs. Velocity is the intensity at which a startup must produce to survive.

A high-growth startup moves at breakneck speed, which I alluded to when I said priorities and economic factors can change daily or weekly.

At that speed, a startup's roadmap must be flexible, bend but not break, and be brief and to the point. I can't tell you how many startups and large companies develop a product roadmap every quarter and then tuck it away.

Big, wealthy companies can do this. It's suicide for a startup.

The drawer thing happens because startup product roadmaps are often valid for a short time. The roadmap is a random list of features prioritized by different company factions and unrelated to company goals.

It's not because the goals changed that a roadmap is shelved or ignored. Because the company's goals were never communicated or documented in the context of its product.

In the previous post, I discussed how to turn company goals into a product roadmap. In this post, I'll show you how to make a one-page startup roadmap.

In a future post, I'll show you how to follow this roadmap. This roadmap helps you track company goals, something a roadmap must do.

Be vague for growth, but direct for execution.

Here's my plan. The real one has more entries and more content in each.

Let's discuss smaller boxes.

Product developers and engineers know that the further out they predict, the more wrong they'll be. When developing the product roadmap, this rule is ignored. Then it bites us three, six, or nine months later when we haven't even started.

Why do we put everything in a product roadmap like a project plan?

Yes, I know. We use it when the product roadmap isn't goal-based.

A goal-based roadmap begins with a document that outlines each goal's idea, execution, growth, and refinement.

Once the goals are broken down into epics, initiatives, projects, and programs, only the idea and execution phases should be modeled. Any goal growth or refinement items should be vague and loosely mapped.

Why? First, any idea or execution-phase goal will result in growth initiatives that are unimaginable today. Second, internal priorities and external factors will change, but the goals won't. Locking items into calendar slots reduces flexibility and forces deviation from the single source of truth.

No soothsayers. Predicting the future is pointless; just prepare.

A map is useless if you don't know where you're going.

As we speed down the road, the car and the road will change. Goals define the destination.

This quarter and next quarter's roadmap should be set. After that, you should track destination milestones, not how to get there.

When you do that, even the most critical investors will understand the roadmap and buy in. When you track progress at the end of the quarter and revise your roadmap, the destination won't change.

And why we must keep arming Ukraine

Russian expatriates write about horrific news from home.

Read this from Nadin Brzezinski. She's not a native English speaker, so there are grammar errors, but her tale smells true.

Terrible truth.

There's much more that reveals Russia's grim reality.

Non-leadership. Millions of missing supplies are presumably sold for profit, leaving untrained troops without food or gear. Missile attacks pause because they run out. Fake schemes to hold talks as a way of stalling while they scramble for solutions.

Street men were mobilized. Millions will be ground up to please a crazed despot. Fear, wrath, and hunger pull apart civilization.

It's the most dystopian story, but Ukraine is worse. Destruction of a society, country, and civilization. Only the invaders' corruption and incompetence save the Ukrainians.

Rochester, NY. My suburb had many Soviet-era Ukrainian refugees. Their kids were my classmates. Fifty years later, many are still my friends. I loved their food and culture. My town has 20,000 Ukrainians.

Grieving but determined. They don't quit. They won't quit. Russians are eternal enemies.

It's the Russian people's willingness to tolerate corruption, abuse, and stupidity by their leaders. They are paying. 65000 dead. Ruined economy. No freedom to speak. Americans do not appreciate that freedom as we should.

It lets me write/publish.

Russian friends are shocked. Many are here because their parents escaped Russian anti-semitism and authoritarian oppression. A Russian cultural legacy says a strongman's methods are admirable.

A legacy of a slavery history disguised as serfdom. Peasants and Princes.

Read Tolstoy. Then Anna Karenina. The main characters are princes and counts, whose leaders are incompetent idiots with wealth and power.

Peasants who die in their wars due to incompetence are nameless ciphers.

Sound familiar?