After 10 years of working in scale-ups, I've embraced a few concepts for scaling Tech and Product teams.

First, cross-functionalize teams. Product Managers represent the business, Product Designers the consumer, and Engineers build.

I organize teams of 5-10 individuals, following AWS's two pizza teams guidelines, with a Product Trio guiding each.

If more individuals are needed to reach a goal, I group teams under a Product Trio.

With Engineering being the biggest group, Staff/Principal Engineers often support the Trio on cross-team technical decisions.

Product Managers, Engineering Managers, or Engineers in the team may manage projects (depending on the project or aim), but the trio is collectively responsible for the team's output and outcome.

Once the Product Trio model is created, roles, duties, team ceremonies, and cooperation models must be clarified.

Keep reporting lines by discipline. Line managers are accountable for each individual's advancement, thus it's crucial that they know the work in detail.

Cross-team collaboration becomes more important after 3 teams (15-30 people). Teams can easily diverge in how they write code, run ceremonies, and build products.

Establishing groups of people that are cross-team, but grouped by discipline and skills, sharing and agreeing on working practices becomes critical.

The “Spotify Guild” model has been where I’ve taken a lot of my inspiration from.

Last, establish a taxonomy for communication channels.

In Slack, I create one channel per team and one per guild (and one for me to have discussions with the team leads).

These are just some of the basic principles I follow to organize teams.

A book I particularly like about team types and how they interact with each other is https://teamtopologies.com/.

People are slowly recognizing entrepreneurship's downside.

Growing up, entrepreneurship wasn't common. High school class of 2012 had no entrepreneurs.

Businesses were different.

They had staff and a lengthy history of achievement.

I never wanted a business. It felt unattainable. My friends didn't care.

Weird.

People desired degrees to attain good jobs at big companies.

When graduated high school:

• 9 out of 10 people attend college

• Earn minimum wage (7%) working in a restaurant or retail establishment

• Or join the military (3%)

Later, entrepreneurship became a thing.

2014-ish

I was in the military and most of my high school friends were in college, so I didn't hear anything.

Entrepreneurship soared in 2015, according to Google Trends.

Then more individuals were interested. Entrepreneurship went from unusual to cool.

In 2015, it was easier than ever to build a website, run Facebook advertisements, and achieve organic social media reach.

There were several online business tools.

You didn't need to spend years or money figuring it out. Most entry barriers were gone.

Everyone wanted a side gig to escape the 95.

Small company applications have increased during the previous 10 years.

2011-2014 trend continues.

2015 adds 150,000 applications. 2016 adds 200,000. Plus 300,000 in 2017.

The graph makes it look little, but that's a considerable annual spike with no indications of stopping.

By 2021, new business apps had doubled.

Entrepreneurship will return to its early 2010s level.

I think we'll go backward in 5 years.

Entrepreneurship is half as popular as it was in 2015.

In the late 2020s and 30s, entrepreneurship will again be obscure.

Entrepreneurship's decade-long splendor is fading. People will cease escaping 9-5 and launch fewer companies.

That’s not a bad thing.

I think people have a rose-colored vision of entrepreneurship. It's fashionable. People feel that they're missing out if they're not entrepreneurial.

Reality is showing up.

People say on social media, "I knew starting a business would be hard, but not this hard."

More negative posts on entrepreneurship:

Luke adds:

Is being an entrepreneur ‘healthy’? I don’t really think so. Many like Gary V, are not role models for a well-balanced life. Despite what feel-good LinkedIn tells you the odds are against you as an entrepreneur. You have to work your face off. It’s a tough but rewarding lifestyle. So maybe let’s stop glorifying it because it takes a lot of (bleepin) work to survive a pandemic, mental health battles, and a competitive market.

Entrepreneurship is no longer a pipe dream.

It’s hard.

I went full-time in March 2020. I was done by April 2021. I had a good-paying job with perks.

When that fell through (on my start date), I had to continue my entrepreneurial path. I needed money by May 1 to pay rent.

Entrepreneurship isn't as great as many think.

Entrepreneurship is a serious business.

If you have a 9-5, the grass isn't greener here. Most people aren't telling the whole story when they post on social media or quote successful entrepreneurs.

People prefer to communicate their victories than their defeats.

Is this a bad thing?

I don’t think so.

Over the previous decade, entrepreneurship went from impossible to the finest thing ever.

It peaked in 2020-21 and is returning to reality.

Startups aren't for everyone.

If you like your job, don't quit.

Entrepreneurship won't amaze people if you quit your job.

It's irrelevant.

You're doomed.

And you'll probably make less money.

If you hate your job, quit. Change jobs and bosses. Changing jobs could net you a greater pay or better perks.

When you go solo, your paycheck and perks vanish. Did I mention you'll fail, sleep less, and stress more?

Nobody will stop you from pursuing entrepreneurship. You'll face several challenges.

Possibly.

Entrepreneurship may be romanticized for years.

Based on what I see from entrepreneurs on social media and trends, entrepreneurship is challenging and few will succeed.

A top-down company plan facilitates decision-making and impresses investors.

A startup business plan starts with the product, the target customers, how to reach them, and how to grow the business.

Bottom-up is terrific unless venture investors fund it.

If it can prove how it can exceed $100M in sales, investors will invest. If not, the business may be wonderful, but it's not venture capital-investable.

As a rule, venture investors only fund firms that expect to reach $100M within 5 years.

Investors get nothing until an acquisition or IPO. To make up for 90% of failed investments and still generate 20% annual returns, portfolio successes must exit with a 25x return. A $20M-valued company must be acquired for $500M or more.

This requires $100M in sales (or being on a nearly vertical trajectory to get there). The company has 5 years to attain that milestone and create the requisite ROI.

This motivates venture investors (venture funds and angel investors) to hunt for $100M firms within 5 years. When you pitch investors, you outline how you'll achieve that aim.

I'm wary of pitches after seeing a million hockey sticks predicting $5M to $100M in year 5 that never materialized. Doubtful.

Startups fail because they don't have enough clients, not because they don't produce a great product. That jump from $5M to $100M never happens. The company reaches $5M or $10M, growing at 10% or 20% per year.  That's great, but not enough for a $500 million deal.

Once it becomes clear the company won’t reach orbit, investors write it off as a loss. When a corporation runs out of money, it's shut down or sold in a fire sale. The company can survive if expenses are trimmed to match revenues, but investors lose everything.

When I hear a pitch, I'm not looking for bright income projections but a viable plan to achieve them. Answer these questions in your pitch.

• Is the market size sufficient to generate $100 million in revenue?

• Will the initial beachhead market serve as a springboard to the larger market or as quicksand that hinders progress?

• What marketing plan will bring in $100 million in revenue? Is the market diffuse and will cost millions of dollars in advertising, or is it one, focused market that can be tackled with a team of salespeople?

• Will the business be able to bridge the gap from a small but fervent set of early adopters to a larger user base and avoid lock-in with their current solution?

• Will the team be able to manage a $100 million company with hundreds of people, or will hypergrowth force the organization to collapse into chaos?

• Once the company starts stealing market share from the industry giants, how will it deter copycats?

The requirement to reach $100M may be onerous, but it provides a context for difficult decisions: What should the product be? Where should we concentrate? who should we hire? Every strategic choice must consider how to reach $100M in 5 years.

Focusing on $100M streamlines investor pitches. Instead of explaining everything, focus on how you'll attain $100M.

As an investor, I know I'll lose my money if the startup doesn't reach this milestone, so the revenue prediction is the first thing I look at in a pitch deck.

Reaching the $100M goal needs to be the first thing the entrepreneur thinks about when putting together the business plan, the central story of the pitch, and the criteria for every important decision the company makes.

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.