I listened to an investor share his life story recently. He’s made some timely investments that have done extremely well. I always enjoy hearing the stories of successful people because most contain a golden nugget (something others can learn from). Most of what you read about such people talks about their successes, but their journeys usually include massive failures. This story was no different. This investor was kicked out of college before he got his act together. My biggest takeaway was the amount of preparation that went into his success. He spent a decade refining his investment style before he realized a sizeable return. Many of his investments went to zero, but he learned from each one.

Some believe the path to success can be short. I disagree. I’ve yet to meet anyone successful who got there overnight. Years, if not decades, of hard work position people for eventual successful.

If you want to do something great, you must be committed and put in the work. There are no shortcuts in life. For those of you who aspire to be successful, settle in—it’s going to be a long ride!

I had a great conversation with another investor who’s had an interesting journey. He worked in corporate America learning hard skills out of undergrad. Then he joined a start-up as an early employee. His skills helped the start-up minimize painful learnings and release a superior product in less time. Equity was part of his compensation package. Eventually, he made his way to venture capital and learned how to invest in early-stage companies. The start-up he’d worked at years before went public, and his early equity turned into a significant financial windfall. He began doing personal angel investments, and now he’s planning to raise a fund to help founders in his area of expertise.  

He understands start-up life and entrepreneurship from various perspectives. Now he’s taking what he’s learned and the wealth he has amassed from his journey and using them to help more founders become successful.

People like this have a huge impact on start-up ecosystems. The combination of capital, operator knowledge, and relationships can be game-changing for early founders. I look forward to watching this investor transition to fund manager. I’m sure he and his team will move his space forward!

I was chatting with a close friend who needed to make a big decision. I listened as he talked through all the things going through his head. He listed the pros and cons of each path he was considering. Toward the end of the conversation, I realized he was afraid to make the wrong decision and his fear had paralyzed him.

As a founder, I learned that indecision could kill my company (a few times, it almost did). I didn’t want my company to die, so I learned to make decisions more quickly. I was still afraid they could be wrong. I got over this by telling myself that incorrect decisions were inevitable, and they weren’t mistakes, they were just painful lessons that improved future decision-making.

As I got more confident in my decision-making and leadership, I learned to distinguish between what my gut was telling me and what my brain was telling me. I realized that my gut usually gave me a quick answer on what I should do, and my brain rationalized why I should do something but it took more time. I eventually figured out that my gut was usually right and leveraged it more in my decision-making. I would listen to my gut to decide what I was going to do (and write it down). If I needed to have others execute the decision, I leveraged my brain to articulate the reasons for my decision. Otherwise, I’d just execute it myself and not worry about the why.

Making decisions is one of the biggest responsibilities of founders. You can’t avoid them or put them off. They must be made. Luckily, everyone can have their own decision-making style, and no one expects perfection. Whatever your approach, always strive to improve it, because the better you get at making decisions the more likely your company is to succeed.

I recently went shopping and encountered a surprising sales style. The salesperson was knowledgeable, but he didn’t seem to care if I bought the product I was interested in. He wasn’t pushy or even trying to close the deal. He merely suggested I test out the product. I did, and I was impressed. A few days later, I bought it. Afterward, I asked the salesperson why he was indifferent to my purchasing decision. He said the product is so great that it sells itself and that if I didn’t buy it, someone else would—he sees a constant flow of people who are ready to buy.

This company has done a great job of understanding the pains of their customer and creating a product that solves them magnificently. Potential customers test the product, immediately see the value it creates, and are ready to pay for that value. The salesperson is there to answer questions, but the product itself is doing all the selling.

Lots of early founders want to focus on sales and marketing after they launch their product. They believe that’s the key to growth. Both functions are important to any business. But in the early days, founders should be laser focused on their product as the key to growth. An amazingly good sales and marketing strategy is to make a product so wonderful that people easily understand the value it creates for them. Happy customers spread the word to others. When those folks try it, they’ll love it and buy it, and they’ll spread the word.

If you’re an early founder concerned about sales and market, ask yourself: Is your product good enough to market and sell itself?

I’ve been following the recent news about Nikola Corp. founder and former chairman Trevor Milton. He’s been charged with misleading investors. I have no views on his guilt or innocence, but his situation reminded me of conversations I’ve had with founders.

Many early founders are optimistic about their companies. To survive, they have to be. The chips are stacked against them. If founders focus on the million things that could go wrong, it’s hard to motivate teams to run through walls. So, many of them see the glass as half full and focus on what could go right. I like this approach. It’s what teams need to do the impossible.

But . . . though optimism is great, there’s a line that founders shouldn’t cross. They should be clear about what has happened versus what they’re planning for. Saying you’ve hired a rock star CTO is different than saying a CTO will come on board shortly when you conclude final negotiations. One’s a done deal. The other’s an expectation. Founders can get themselves in hot water if they position something as having already been concluded when it hasn’t. Even if it’s highly likely it will happen soon. Maybe it won’t. Maybe Murphy’s Law will kick in. Or maybe the founder’s view of what’s “highly likely” is skewed by his rose-colored glasses.

Founders should be optimistic but also clear with all stakeholders. Optimism without transparency will erode trust over time. If a team doesn’t trust its leader, it’s doomed.

One of my biggest takeaways from my time in corporate America was that every company has issues. I was doing consulting work, which basically meant my team helped companies solve problems they couldn’t solve on their own. I was fortunate enough to count some of the biggest Fortune 500 companies as clients. I’m talking iconic brands in Super Bowl commercials. From the outside looking in, I thought these companies had it all figured out and were well-oiled machines (kudos to their marketing departments). In reality, I usually found a large and constantly evolving organization that had a serious problem in a core area —one that wasn’t materially impacting revenue yet but that could derail the company if left unaddressed.

When I talk with early founders now, I try to remind them that every company has weaknesses. It’s normal. The great founders I know are aware of the problems in their companies and working to address them. It’s a never-ending cycle. They communicate their issues to others and seek help to resolve them. (When people have a clear understanding of what you need help with, they’re more likely to help you.)

If you’re a founder and feel you must present your company as perfect, I suggest you think again. Perfection doesn’t exist in business. Being open with others about your issues could be the key to resolving them!

When I was working in corporate America, I knew I wanted to become an entrepreneur full-time. And I knew I needed flexibility and capital to make that dream a reality. I avoided long-term obligations and saved as much of my salary as possible. Then all my friends started buying houses, and I began suffering a bit from FOMO. So, I went out and bought a home too. It required me to put down a large sum of capital and locked me into a long-term financial obligation.

I didn’t know anything about raising money from investors, so I funded my company with customer revenue and my savings. My entrepreneurial journey was full of ups and downs, and often I regretted not having the capital I’d put into a home to invest in the company. I enjoyed having a place I could call my own, but I owed the bank a lot of money. And it made sure to remind me of that every month. Seeing that loan balance on my monthly statement definitely affected how I made decisions.

In the end it all worked out, and I was able to grow the company to over eight figures in revenue. Looking back, though, I realize that I didn’t act in alignment with my goal. The decision to buy a home didn’t better position me for entrepreneurship. It did the opposite. I had less capital to put toward my company and a long-term obligation that reduced my risk tolerance.

My goal was different than my friends’ goals. So, my actions should have been different too. I’m very thankful for the journey I had and wouldn’t change a thing. But I did learn from it and begin thinking about my actions and goals differently. I now look at any major action I’m contemplating and ask myself if it will get me closer to or further away from my goal. If it doesn’t move me closer, I don’t proceed.

If you’re a founder considering a material action, ask yourself: Does this align with my goals? That question can prevent you from doing things you’ll regret and give you the confidence to take high-risk actions.

Speaking with a founder today reminded me of my days as a founder. He and his team have a great product and they’re focused on producing as many of them as possible to get them in the hands of customers. It’s early days for them, and naturally they don’t know everything. They’re still trying to find product–market fit.

I remember a time I had a bright idea at CCAW: let’s add a ton of new distribution centers all at once. We literally flipped a switch one day and added over a dozen massive warehouses to our distribution footprint. What could go wrong? Um . . . huge problems kept orders from being in customers’ hands when they expected them. Working through the various reasons this happened was painful and stressful for our team.

I later realized that we had trained our valuable energy on the wrong thing: growing our distribution footprint and revenue. We didn’t have product–market fit yet, so we should have been listening to our existing customers, not executing a land grab to get new ones. We missed out on valuable customer insight during a critical phase of our startup journey. The company still scaled and was successful, but I believe that missed insight was the difference between eight figures in revenue (which we achieved) and nine (which we did not).

Focusing on the right thing at the right time is critical for early-stage companies—there’s only so much bandwidth to go around. If I could do it all over again, I’d work on understanding my customer’s problems before adding operational complexity to acquire more customers.

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With more companies working remotely, I’ve been hearing more founders searching for ways to keep their teams connected on a deeper level. Some of them are putting more thought into their retreat planning. Retreats are usually meetings outside the office where everyone gets together to bond and discuss the business. Some last one day; others are multiday. Many include team-building activities to allow team members to overcome a challenge together.

I’m a big fan of retreats and attended two a year before the pandemic. Most were for two to four days and attended by other entrepreneurs. Without a doubt, these have been some of the most transformative and enlightening experiences I’ve ever had. I’ve always left more focused and excited about what lies ahead.

Retreats were helpful before the pandemic, but I think they will be a critical tool for leaders going forward. Can’t wait to see all the creative ways people find to get teams to bond.

As a founder, sometimes it’s easy to get caught up in seeing things your way. You see an opportunity and a path to pursuing it. You’re locked in and focused. Founders often miss that their way isn’t the only way or always the best way. As the old saying goes, there’s more than one way to skin a cat.

Founders should be locked in on a destination but not necessarily a path. They should be searching for the best path to get to the desired destination. Sometimes that path will be something they thought of, and sometimes it will come from others. That’s one reason I’m a big fan of founders sharing their ideas with other people. Sharing invites feedback, some of which will be valuable insights.

If you’re a founder going after a great opportunity, consider taking time to solicit feedback. You never know, you might just uncover the yellow brick road to your Emerald City.