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.

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.

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.

Fixing problems isn't enough.

Numerous articles and how-to guides on value propositions focus on fixing consumer concerns.

Contrary to popular opinion, addressing customer pain rarely suffices. Win your market category too.

Core Value Statement

Value proposition usually means a product's main value.

Its how your product solves client problems. The product's core.

Answering these questions creates a relevant core value proposition:

• What tasks is your customer trying to complete? (Jobs for clients)

• How much discomfort do they feel while they perform this? (pains)

• What would they like to see improved or changed? (gains)

After that, you create products and services that alleviate those pains and give value to clients.

Value Proposition by Category

Your product belongs to a market category and must follow its regulations, regardless of its value proposition.

Creating a new market category is challenging. Fitting into customers' product perceptions is usually better than trying to change them.

New product users simplify market categories. Products are labeled.

Your product will likely be associated with a collection of products people already use.

Example: IT experts will use your communication and management app.

If your target clients think it's an advanced mail software, they'll compare it to others and expect things like:

• comprehensive calendar

• spam detectors

• adequate storage space

• list of contacts

• etc.

If your target users view your product as a task management app, things change. You can survive without a contact list, but not status management.

Find out what your customers compare your product to and if it fits your value offer. If so, adapt your product plan to dominate this market. If not, try different value propositions and messaging to put the product in the right context.

Finished Value Proposition

A comprehensive value proposition is when your solution addresses user problems and wins its market category.

Addressing simply the primary value proposition may produce a valuable and original product, but it may struggle to cross the chasm into the mainstream market. Meeting expectations is easier than changing views.

Without a unique value proposition, you will drown in the red sea of competition.

To conclude:

1. Find out who your target consumer is and what their demands and problems are.

2. To meet these needs, develop and test a primary value proposition.

3. Speak with your most devoted customers. Recognize the alternatives they use to compare you against and the market segment they place you in.

4. Recognize the requirements and expectations of the market category.

5. To meet or surpass category standards, modify your goods.

Great products solve client problems and win their category.

Bear markets don't last forever, but that's hard to remember. Jamie Cullen's illustration

A bear market is a 20% decline from peak to trough in stock prices.

The S&P 500 was down 24% from its January highs at its low point this year. Bear market.

The U.S. stock market has had 13 bear markets since WWII (including the current one). Previous 12 bear markets averaged –32.7% losses. From peak to trough, the stock market averaged 12 months. The average time from bottom to peak was 21 months.

In the past seven decades, a bear market roundtrip to breakeven has averaged less than three years.

Long-term averages can vary widely, as with all historical market data. Investors can learn from past market crashes.

Historical bear markets offer lessons.

Bear market duration

A bear market can cost investors money and time. Most of the pain comes from stock market declines, but bear markets can be long.

Here are the longest U.S. stock bear markets since World war 2:

Stock market crashes can make it difficult to break even. After the 2008 financial crisis, the stock market took 4.5 years to recover. After the dotcom bubble burst, it took seven years to break even.

The longer you're underwater in the market, the more suffering you'll experience, according to research. Suffering can lead to selling at the wrong time.

Bear markets require patience because stocks can take a long time to recover.

Stock crash recovery

Bear markets can end quickly. The Corona Crash in early 2020 is an example.

The S&P 500 fell 34% in 23 trading sessions, the fastest bear market from a high in 90 years. The entire crash lasted one month. Stocks broke even six months after bottoming. Stocks rose 100% from those lows in 15 months.

Seven bear markets have lasted two years or less since 1945.

The 2020 recovery was an outlier, but four other bear markets have made investors whole within 18 months.

During a bear market, you don't know if it will end quickly or feel like death by a thousand cuts.

Recessions vs. bear markets

Many people believe the U.S. economy is in or heading for a recession.

I agree. Four-decade high inflation. Since 1945, inflation has exceeded 5% nine times. Each inflationary spike caused a recession. Only slowing economic demand seems to stop price spikes.

This could happen again. Stocks seem to be pricing in a recession.

Recessions almost always cause a bear market, but a bear market doesn't always equal a recession. In 1946, the stock market fell 27% without a recession in sight. Without an economic slowdown, the stock market fell 22% in 1966. Black Monday in 1987 was the most famous stock market crash without a recession. Stocks fell 30% in less than a week. Many believed the stock market signaled a depression. The crash caused no slowdown.

Economic cycles are hard to predict. Even Wall Street makes mistakes.

Bears vs. bulls

Bear markets for U.S. stocks always end. Every stock market crash in U.S. history has been followed by new all-time highs.

How should investors view the recession? Investing risk is subjective.

You don't have as long to wait out a bear market if you're retired or nearing retirement. Diversification and liquidity help investors with limited time or income. Cash and short-term bonds drag down long-term returns but can ensure short-term spending.

Young people with years or decades ahead of them should view this bear market as an opportunity. Stock market crashes are good for net savers in the future. They let you buy cheap stocks with high dividend yields.

You need discipline, patience, and planning to buy stocks when it doesn't feel right.

Bear markets aren't fun because no one likes seeing their portfolio fall. But stock market downturns are a feature, not a bug. If stocks never crashed, they wouldn't offer such great long-term returns.