The Lonely Entrepreneur's Michael Dermer Shares 10 Pieces of Advice on the Startup Journey

If you turn to Google for advice on how to improve your entrepreneurial or leadership skills, you’ll likely end up overwhelmed by the pages and pages of results that come back. Another option is to listen and learn from people who’ve been in your shoes before. Michael Dermer, Labs mentor and founder and CEO of The Lonely Entrepreneur, hosted a Labs session on how to become the best entrepreneur and leader you can be based on his own experiences and insights. Here are 10 key takeaways to remember as you launch and grow your company.

1. Find playgrounds where no one else is playing

“When you bring something to market, focus on the path where your competition is not playing,” Dermer says. “It’s unlikely that you’ll develop something truly unique on a regular basis, but it is likely that you’ll find an ‘empty playground’ or a unique distribution channel where your idea will thrive. Look at competition and success from a different perspective. Take some of the time, effort, and resources normally devoted to your product, and direct them to finding the right ‘playground’—one where you can maneuver and gain visibility that cuts through the noise.”

2. Positioning is more important than product

“One of the most important aspects of marketing your company or product is its position in the market. It’s the best way to separate yourself from the competition, especially if you’re in a crowded space,” Dermer says. “I’ve seen far too many companies build their product or service and then leave the product’s positioning to the marketing department. People rarely pay attention to each of the features and functionalities, but strong positioning always stands out. In order to find sufficient demand in the market, a company not only needs to solve a real pain for target customers but it also needs to find an effective approach to communicate its product’s value. Product-market fit does not exist without message-customer fit. The right message needs to repeatedly reach the right customer in the right market to validate the startup’s existence.”

3. Don’t build a rocket when there are other rockets you could use

“Do we always have to build something from scratch? Could we have a different perspective? Could we see if building could be replaced with partnerships with those who have the capital and resources we lack? Think of this ‘strategic partner’ approach as just another way to bring your vision to life,” Dermer says. “Some entrepreneurs may view this as a ‘cop out’—that real entrepreneurism requires building from the ground up. Don’t think of it this way. This type of partnership is an entrepreneurial venture coming to life through a different path.”

“Companies will scrutinize your offering and its value to them and whether a strategic partnership is the right choice for both parties. Choosing this path will require you to hone your approach, your communication, and the details you highlight in order to specifically address the benefits of your idea to a prospective partner. Your strategic partnership doesn’t have to or may not involve your entire concept or every product, so be prepared to differentiate the scope of your vision and offering.”

4. Know what inning you’re in

“When an idea or product is unique, it’s new to the market. This may be what makes it sell, but it’s also what makes the market slow to comprehend and adopt your innovation,” Dermer says. “So one of the perspectives we must develop is the ability to clearly judge how ready the market is for your solution. In baseball terms, we have to know what inning we are in. Understanding what inning you’re in is critical to establishing the right pace for your company, setting expectations for your team and other constituents, and aligning capital and other resources.Be conservative. Take the opinion of your most skeptical employee, advisor, or investor. It’s better to set the expectation that your film will take two years to complete and deliver it early than to suggest it will be finished in eighteen months and have it take a full two years.”

5. Process is not a dirty word

“You must recognize and understand that process is an enabler that accelerates, not decelerates, your activity,” Dermer says. “You’re going slow so you can go fast. What if you had a sales presentation that could be used in a variety of customer meetings by changing just one slide? Or a clear structure for determining pricing that all your managers share? Or even if you’re running a solo business, having a process set up for shipping— labeling software, postage meter, scale, FedEx materials, and scheduled pick ups—is much more efficient than digging for supplies and running to the post office every time you need to ship your product. Process also allows you to be productive, efficient, and to focus on the substance of your business.”

6. An investment process is key to getting funding

“You have to make the investment process efficient by creating a standard process that can be used for all investment opportunities,” Dermer says. “While the process may vary slightly, your goal here is to control the process versus letting the process control you. This enables you to focus not on reinventing the wheel each time, but on honing your message so potential investors see the value of your business. The way you manage your investment process is also an indication of how you manage your business. A structured and organized process, with set tools, meetings and agendas, and clear messages, shows the type of discipline that investors value. When an investment process seems ad hoc, with days going by between asks and a scramble to put materials together, investors notice the lack of structure and discipline of the business. Don’t forget investors are always watching.”

7. You have to step up and be the CEO

“There’ll be plenty of times that you debate with yourself and others whether you’re qualified or even want to be the CEO of the company,” Dermer says. “Whether you’re eager for the position or pushed unwillingly to it, you must be the CEO during the entrepreneurial launch stage of your company. That requires doing many things like setting the priorities of the company and aligning the organization to those priorities, ensuring that the company is properly funded, inspiring people to stick to the vision, and clearly communicating with the various constituents of the company.”

“Being the CEO of an established company is hard enough, but being the CEO of a developing business is the ultimate baptism by fire. In most cases, you do it all without formal training. It takes most leaders their entire career to develop the skills of a good CEO. Is it fair to expect you to learn all the skills of a CEO when it takes most a lifetime? Of course not. But too bad—you have to learn those skills in a fraction of that time.”

8. Be humble and seek to learn

“One of the most important lessons I learned at my company was that it’s a blessing to acknowledge when you come across something you don’t know, not a curse,” Dermer says. “It’s critical that you understand, recognize, acknowledge, and embrace your flaws and the company’s shortcomings. Entrepreneurs are driven, intelligent, and confident. Not knowing something seems like a sign of weakness. It’s the opposite. Humility is a trait of strong leaders—the type of leaders employees want to work for and investors want to fund. One of the most important days in the history of my company was when I realized being a CEO was a skill that needed to be developed with the same perseverance, ferocity, and willingness to learn that athletes apply to their training. Once you embrace this as an opportunity, you won’t be wasting time criticizing yourself for a lack of knowledge. Instead, you’ll embrace the opportunity to learn and grow.”

9. Know where you need help

“Identifying where your skills can be supplemented or complemented can quickly accelerate your company’s growth. Once you recognize these areas, you can plan accordingly,” Dermer says. “Look for a variety of resources with experience that balances yours. Find support from specialists or those with extensive experience in an area you’re lacking. Their ease and efficiency will translate into your own effectiveness. Being candid with yourself and your constituents is not a weakness; it’s a strength. Leaders who recognize their deficiencies and encourage others to do the same gain respect, solve business issues more efficiently, and set the foundation for well-run companies. There’s also a good chance your day will be much more enjoyable.”

10. You can’t evaluate your life in the middle of the fight

“It's natural for people to start analyzing their lives and happiness when things don't go according to plan or when they’re under immense pressure,” Dermer says. “However, for the entrepreneur, that's everyday life. We tend to forget why we started on this journey in the first place. There must be time for you to reflect, think about the big picture and evaluate your personal goals. Not having this time to reflect can be damaging. The problem is, entrepreneurs often feel compelled to investigate their personal life only at the busiest, most inopportune moments in the middle of the business day. This is precisely the time not to do it. This is a subtle perspective shift but one that can have a real impact. Taking the time to check in with yourself is critical. But you can’t fight the fight and evaluate your life at the same time. Set a time for yourself every two weeks to check in and take stock of yourself. Put it on your calendar and never miss it.”

This post is based on content from a WeWork Labs programming session.

Interested in connecting directly with this mentor? Ask your Labs Manager for help.

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