Yesterday I shared (see here) that a friend who is an entrepreneur learned how to work—meaning how to work efficiently and consistently to meet goals—while employed by a large corporation known for its world-class training. That’s more the exception than the norm, in my opinion. Most people don’t get world-class training on how to work. That got me thinking about myself—how did I learn how to work?

Thinking back, this isn’t something I was ever taught. Not in college and not in corporate America. After I became an entrepreneur, I felt like I was drowning in a never-ending to-do list. I was stressed out. That pain helped me realize that how I was working wasn’t sustainable or effective. So, I sought out other entrepreneurs and asked them how they worked. Over time, I pieced together a system that worked to some extent. But it wasn’t until years later that I read books on the topic that helped me understand what a methodical approach to work looks like and how to implement one.

Now I’m curious. How do most entrepreneurs learn how to work? I don’t know the answer, so I’m going to ask a few and see. My gut tells me that many don’t know how to work and are stressed out—and that those who do know are self-taught out of necessity. Let’s see if I’m right.  

This week, I caught up with a friend who’s an entrepreneur. During our chat, I inquired about how he works. How does he determine what he’s working on each day? How does he know what needs to be done for each objective or project he’s working on? You get the idea. He said that he learned how to work—meaning he learned the process of working efficiently and consistently—while employed by a large corporation known for its world-class training. But that was a few decades into his career.

What I took away from this conversation is that most people are never taught how to work. They’re taught skills, and they gain expertise. But they’re never taught how to effectively execute their skills from day to day to accomplish goals or objectives. Instead, they try to remember and manage everything in their head and end up stressed or burnt out as their responsibilities at work and home increase.

To take this a step further, entrepreneurs experience many times more pain than the average person because of not knowing how to work. They often start out by doing literally everything in the business—much of which they have zero skills or experience in. Over time, many of them experience high levels of stress and anxiety because of this, which causes other problems.

My big takeaway is that the costs of never being taught how to work are high, especially for entrepreneurs.

Yesterday, I shared an interview featuring Howard Marks and his four steps to dealing with change (see here). Toward the end of the interview, Marks talked about his partnership with one of his Oaktree Capital cofounders, Bruce Karsh. He described partnership as an important part of a healthy work environment, which he has with Karsh and other Oaktree Capital founders.

So what’s the key to healthy partnership? Marks has a simple framework. Here’s the key to a healthy partnership (in all aspects of life):

• Shared values – You have to believe the same things about how you want to operate in the world. Marks gave the example that he and Karsh shared the view that they should invest by seeking moderate gains and avoiding losses. Said differently, they would aim for consistent returns rather than grand slams. Neither believed in shooting for the stars. Their values regarding their investment strategy were the same.
• Complementary skills – The key to success is having a well-rounded team that covers all the important areas—the team is strong in all key areas although each individual is not. If you have a team of really smart people who all specialize in the same thing, the team has a skill set hole that will likely cause execution and other issues. A better approach is to work with people who are strong where you’re weak, so you complement each other. This enhances the team’s ability to execute, and people won’t be stepping on each other’s toes.

I agree with Marks. I think partnerships that have both these things can do well. My gut tells me that many people understand the second point and seek complementary skills—opposites attract. But I don’t think as many people understand how important shared values are in a partnership. If you have complementary skill sets but polar-opposite views on how to go about things, you’re bound to have a day of reckoning and maybe even a huge blowup between partners.

If you’re interested in Mark’s full thoughts on partnership, take a listen here.

This week, I was catching up with an entrepreneur. It’s the end of the year, so I asked how 2025 has been for them. It’s been hard, they said. They feel like they’ve been getting beaten up all year and that nothing has gone their way. They survived the year but aren’t excited about what the future holds.

As they talked, it became apparent that they’ve navigated very painful situations in their business this year. While this entrepreneur was a bit pessimistic, I was more optimistic for them. Why? I think that pain is a necessary component of growth. Very rarely do people who achieve outsize success do so without first experiencing a period of what feels like extreme pain.

Why can pain be a good thing? Because what you learn from painful experiences becomes critical to helping you successfully navigate future situations. You learn lessons and gain wisdom that improve your decision-making. Better decision-making leads to more rewarding situations and more wins.

I think Ray Dalio put it best in his book Principles when he said this:

Pain + Reflection = Progress

I’m excited for this entrepreneur. I hope they take the time to reflect on the pain they’ve experienced so they can set themselves up to make serious progress in their business in 2026.

This week, I had a long conversation with a start-up lawyer I’ve known for almost a decade. We talked about what’s new and what we’re thinking about for 2026. He shared that he thinks AI is decimating the legal profession. Clients are using AI tools to handle more legal work, and much of what those tools generate is of good enough quality to accomplish their goals. Side note: I know of a company that used ChatGPT to generate all its legal documents when it made an offer to acquire another company, and the deal closed. They saved probably $50,000 in legal fees.

He shared with me that clients are hesitant to use him as much as they’d like because of the several hundred dollars per hour he charges. Anytime they call for something small, they know the meter is running and they’ll get a bill. So they’re using ChatGPT and other tools for small things. As they use those tools, they’re realizing the output is good enough to meet a lot of their legal needs. They’ve become more comfortable using AI as their first go-to for legal, which means they’re reaching out to their lawyers less and less.

So, what’s this lawyer going to do? He’s changing his pricing model and service offering in 2026. He plans to offer clients the option to pay a flat monthly subscription fee so they can reach out as needed without being billed hourly. As part of this service, he’ll teach his clients how to set up AI to better meet specific legal needs. His thought is that if he makes it easier for clients to use him, they’ll engage him more. And by showing them how to use AI for legal, he becomes a trusted advisor.

I wasn’t expecting to hear this from him, but it made a lot of sense. I never built legal costs into my company’s budget because the number of hours we’d use in a year varied wildly, making it hard to predict. So when we did need legal advice, I always tried to limit the scope to avoid blowing our budget. If I could have paid a flat monthly fee, I probably would have, because that would have made it easy to add legal as a line item in my budget. If I’d had that option, I definitely would have engaged our lawyer more frequently.

It's interesting to hear from someone boots on the ground how big an impact AI is having on the legal profession. I’m curious to learn how his clients respond to his pricing model change and whether the legal profession becomes more creative as AI becomes a larger part of clients’ daily workflow.

This week I talked to an early-stage founder I’ve known for a few years. So far, he has bootstrapped his company. It started as an agency, and he’s now built software that he sells. His target market is micro SMBs that drive revenue by engaging in outbound sales. The founder has some traction, and he’s looking to raise funding from venture capitalists to scale the software.

He shared with me that he’s considering targeting enterprise customers because that’s a clear path to raising from VCs. The micro SMB market doesn’t have a clear path to acquiring customers. He’s found that it’s tough for VCs to understand the potential in that market and to see how capital raised would lead to new customers. With enterprise, the path is clear, and they get it.

This founder is in a tough spot. As I shared earlier this year (see here), micro SMBs isn’t a market that VCs easily understand. The process for acquiring customers lacks a defined playbook, which makes investors hesitant to back software founders targeting this market.

I’ve watched this founder work for some time now, and I think he’s on to something. I’m not sure that enterprise is the right market for him to go after at this time; that’s something he’ll have to decide. If he decides to stick to the micro SMB market, I suspect he’ll raise from VCs only after he has derisked the customer-acquisition process. Once he can show that he has figured out how to find and acquire micro SMBs repeatably and that the product is valuable to them, I think VCs will get on board and cut checks. Heavy product usage by paying customers is a strong signal that a savvy investor never ignores. They may not agree with going after micro SMBs, but they’ll never argue with data like that.

This week, I listened to a founder pitch his early-stage start-up. The company raised a few hundred thousand dollars a few years ago. Today it’s out raising another $500k to $750k, which it hopes to complete in the next few months.

The company is growing, but it’s not growing rapidly. So I was curious about what milestones they plan to hit with the capital they’re raising. The company wants to extend its runway by a year or two to give it time to reach breakeven.

When investors put money into a company, they’re looking for a return that’s high enough to justify the risk of capital loss they’re assuming. Their ROI can be through appreciation of the company’s value (i.e., their stake is worth more) or through dividends the company distributes from its free cash flow.

When a company is at breakeven, it’s neither losing money (consuming cash) nor making money (generating cash). It’s covering expenses to keep the lights on. If a company is growing rapidly and is at breakeven, that can be a good situation. Cash generated by the company’s operations is being reinvested in growth initiatives. In theory, if it stopped investing in growth, it would have cash available for dividends or a rainy day. But if the company is at breakeven and not growing, or growing slowly, that means it’s generating just enough cash to maintain itself, with little left for anything else.

Breaking even is a key milestone for a company because it means it’s self-sustaining: totally funded by customer revenue. But if a company is raising capital from investors with breakeven as its goal, it’s important to keep in mind that investors are seeking a return. Breaking even means there won’t be cash to pay dividends to investors, so the investors will be looking for their ownership to be worth more. If the company is breaking even but not growing revenue at a material rate and therefore not increasing its valuation, no clear path to an ROI exists. The likelihood that investors will agree to put money into the company is low.

Any founder raising capital to reach breakeven should consider how they’ll generate a return on the capital they’re seeking from investors and include that info in their pitch.

A few weeks ago, I was reading a blog post about Costco and its founder, Sol Price. I’m familiar with the discount warehouse retail model because I’ve read biographies about the Home Depot founders, Bernie Marcus, Arthur Blank, and Ken Langone. The post I was reading thoroughly explained not just what Costco’s business model is but also why it’s been so successful. A key thing that stood out to me was how its membership model acted as a filter. It weeded out unprofitable customers and attracted highly profitable, loyal, repeat customers. That really got my wheels turning about my old company, given that it was retail oriented and we never figured out how to consistently attract the type of customer we wanted.

My takeaway is that I should have studied more businesses and industries when I was running my company. Because I didn’t, I tended to follow what others in my industry did—their business models and go-to-market strategies. What I didn’t realize was that there are tons of other models and strategies that people smarter than me had figured out. I could have borrowed from those to create something “innovative” in my industry, which would have given us a competitive advantage and likely increased profitability too.

I was “too busy” to focus on anything but my own business. But what I didn’t realize was that studying other founders and businesses would have made me more aware of the possibilities in business. That increased awareness would have helped me create better solutions, faster, to my business problems. All of which would have benefited my business tremendously.

I now believe that to achieve outsize success in the game of business, you must be a student of the game. ’m not a lifelong student of the game of business, but I’m making up for lost time now.

This week I listened to an entrepreneur explain an interesting situation with a large pilot customer. He’d had a six-month contract for a paid pilot with a large company. The idea was for the company to test his software and then agree to a longer-term contract. Because of internal dynamics at the large company, the pilot ended without a new contract being signed. So, the entrepreneur disabled the customer’s access to his software platform.

An interesting thing happened. The company reached out and asked if they could still access the platform while they worked toward another contract (which was expected to take several more months). Said differently, they wanted access to the platform again even though a new contract hadn’t been agreed upon and they weren’t paying the entrepreneur. The entrepreneur was in a tough spot because he didn’t want to say no and jeopardize ongoing contract negotiations. But he didn’t want to get the large company used to accessing his software for free either. He wasn’t sure whether to grant them access as a good-faith effort or to ask for advance payment.  

While this situation didn’t feel great to the entrepreneur, I viewed it as an overall positive that showed his software is valuable to this large customer. A classic product–market fit question is “What would you do if this service or product went away?” If the customer is unbothered, then you know the solution is a nice-to-have; they can live without it. You either don’t have product–market fit or the problem you’re solving isn’t painful enough to the customer. Neither is a positive sign. If the customer is worried about it going away, that’s a great sign that the solution solves a serious pain point and is a must-have for them. A very strong signal.

This founder’s situation went a step further. When he disabled access, his large customer requested that it be restored. To me, this is a sign that his software is solving a serious pain point for that customer. They’d grown used to his solution, and when it was removed, the pain was real and they realized how much they needed it. The sequence of events that led to this wasn’t ideal. Rolling the pilot into a new long-term contract without service disruption would have been ideal. But if I had to bet, I’d say this customer will end up agreeing to a longer-term contract with this entrepreneur.

I’ve been coaching a friend as she launches a new business. She used an AI website builder to create a fairly complex e-commerce website. The site is live and she’s open for business—a huge milestone. Now she’s tackling her next problem: how to make people aware of this new business.

It’s a classic dilemma. Some entrepreneurs have a field-of-dreams mentality: If you launch a business, customers will automatically come. The reality can be more discouraging. Building a new company or product is hard and forces you to learn new things. But the journey isn’t over when you check that box. Quite the opposite—the journey’s just beginning. You’ve finished a segment of it, and another one that you’re likely equally unfamiliar with awaits you.

Finding those early customers isn't easy, but it’s something you must figure out. If you don’t, you have no business. I’m excited for my friend as she embarks on the next part of her journey. I’m not sure how she’ll find early customers, but I’m pretty confident that she’ll figure it out and gain valuable insights as she does.