Business Transformation
Ryan Robinson is an entrepreneur and online educator who has been featured on Forbes, Entrepreneur, Inc., and more. He teaches his readers how to start and grow a profitable side business on We recently sat down with Ryan to hear about his successes and failures, and to learn about the skills needed to succeed as an entrepreneur.

Tell us a little bit about your entrepreneurial experience. Why did you decide to start a blog?

I started my blog with a simple hypothesis: I thought I could use my experiences of both the successes and failures of starting a business to help others avoid some of the most painful mistakes I’ve made as an entrepreneur. One of my first blog posts on how to start a business while working full-time was actually a minimum viable product for testing the potential of creating an online course on the subject of teaching others how to launch a side business. After it quickly picked up momentum in a few online forums for entrepreneurs, I began building an email subscriber base and continued to write in epic detail about my various different experiences as an entrepreneur. That progression has continued with monthly posts.

I now write for over 200,000 monthly readers and nearly 25,000 people get my weekly email updates. I attribute much of the success with my blog to my skill and drive to find and tap into new communities of people who could benefit from my content, and to repeatedly get in front of that audience. That’s why I’ve worked my ass off to secure contributor relationships with Forbes, Entrepreneur, and several other major online publications.

As an entrepreneur, what was the most difficult skill that you had to learn?

How to effectively manage opportunities. What we decide to create and spend our time on is incredibly important in business. It’s tempting to waste time tweaking your logo, designing business cards, optimizing landing pages, obsessing over copy, and so on. However, these activities often aren’t yielding the highest return on time spent. They’re not bringing us measurably closer to achieving our dreams.

As I’ve started to experience a level of success and authority within my industry, the number of opportunities that come my way has skyrocketed. This has made it much more difficult to continue building upon my success because there are now a constant flow of distractions like podcast interviews, guest posts, offering quotes for articles, and giving advice. These distractions are disguised as ego-boosting, audience-building opportunities that actually just hinder me from creating and delivering my best work. While these types of activities certainly provide some benefit (and make me feel good), they don’t really help me advance the goals that are most important in the short-term. So, I’ve built a serious opportunity management system that I now use to evaluate all internal and external opportunities for how I could spend my time. The sooner you give yourself permission and establish clear criteria to determine what you should be spending your time on, the more effective you’ll be at eliminating distractions and using all of your energy to drive yourself forward toward your most important goals.

You talk about your road to sustaining a profitable business and some of the obstacles you had to overcome

Could you tell us about such an instance and what you learned?

My biggest “holy s**t!” moment as an entrepreneur was the day I admitted to myself that I’d have to throw in the towel on a business and move back in with my parents. It happened just a year or so after I graduated from college from Chapman University down in southern California. My best friend Matt and I started a business together, and we both left our day jobs shortly thereafter. While the business almost immediately brought in revenue and was nearly profitable, we realized that it wasn’t profitable enough and it wasn’t going to grow quickly enough to support two full-time incomes. We had quit our day jobs about six months too early, and now we had to deal with the consequences of that decision. For both of us, that meant moving back to our hometowns on opposite sides of the country and focusing on scaling the business while we had lower costs of living at home.

That kicked off what would become one of the most difficult times of my life. My hometown is located in the rural central valley of California and has a larger population of cows than it does people. My only real contacts there were family, since the high school I had gone to was also out of the area. One week I was living with my best friends just a block from the sand at Newport Beach, and the next minute I was 300 miles away from my network of people.

It took us significantly longer than we thought it would to grow the business; and after another 6 months, we still weren’t able to reach a point where it could support both of our lifestyles. So I made the decision to remove myself from the company. Matt and I worked out a long-term buyout plan to slowly transition me out of the company without bankrupting it, and we kept me on as a paid consultant and I moved to San Francisco to run marketing for an online education startup. I promised myself that I’d never again leave my day job without having a dependable substantial income, enough to at least cover my living expenses while running a side business. Just this summer, I finally took my freelance business full-time and nearly doubled my income. It took me almost two years to recover from the effects of quitting my day job too soon, which is why I’ve dedicated myself to teaching others how to start and grow their own side businesses, too.

If someone were to say to you, “I’d like to start my own business, but I’m afraid that I might fail,” what would be your response?

I fail multiple times a week within my business. If you’re not taking (calculated) risks, failing, and pushing yourself to grow and learn, you’re going to live a life that’ll leave you wondering what could’ve been if you’d have just taken those chances or risks. Take a brutally honest look at where you’re at in your life right now. If you were to risk failure and choose to start your own business, let’s say you lose all of your savings over the course of a year. How difficult would it be to get back to where you are now? Sure it’d suck, but if you’re willing to hustle hard, restrict your lifestyle down to just the bare essentials, get a job that pays well, and do whatever you can to rebuild your savings, I guarantee you could do it very quickly. I frequently ask myself this question, because the answer is always that it wouldn’t be that difficult to get back to where I am right now today.

I’d way rather fail at giving 100% of my effort to building something I care deeply about than to look back with regret wondering what could’ve happened in a year or two. We tend to build up the fear of failure and let it hold us back from trying things that could potentially change the course of our lives for the better. Yes, failure can cripple you for a brief moment, but you will bounce back. And you’ll get back into the game with a new level of experience, relationships and most of all skills that’ll help you seriously kick ass the next time around.

For someone who wants to build a new business while keeping their day job, what might they expect? What changes will they have to deal with in their lives?

You’ll need to make short-term sacrifices, but they’ll help you create the lifestyle you want in the long-term. The biggest challenge most people have with starting (and sticking to) a side business is freeing up meaningful blocks of time and committing to working on the business when they say they will. If you want to make quick progress, you really need to free up at least 15 to 20 hours of time to dedicate to your business each week. That time has to come from somewhere, so we go through a few detailed activities that help students re-prioritize what’s most important in their lives at this juncture. We’ll loosen some non-essential responsibilities, remove others, and cut back on the time we spend watching tv and hanging out with friends in the short term so that we can achieve our long-term goals. It’s easier to hit snooze on your alarm at 4:30am than it is to get out of bed and start working on your business before anyone else is awake. In my course, students train themselves to set realistic expectations, create a system of incentives that rewards them for holding their side business commitments, and helps them reach their goals.

As you point out, there are business ideas and there are profitable business ideas. How can someone tell if their idea is profitable?

To really prove whether or not your business concept has potential, you have to determine the most absolute basic way you can provide value to your target customers. Don’t rush to spend money, develop a product, or build a website to promote your solutions. To create a business, you need to provide value and help people solve a problem. It doesn’t cost any money to provide value. Take the problem you want to solve and create a very manual, minimalist solution that is free (or inexpensive) to implement while being replicable and reliable. Once you can call yourself an expert at solving this specific problem for a group of people you’re motivated to help, you can move forward and start to productize your solution so that you can scale your impact without needing to be directly involved with each person.

Here’s an example: If your friends frequently come to you for dating advice or turn to you for great cooking recipes on a regular basis (and you enjoy doing it), that’s a huge clue as to what type of business you should consider starting. However, don’t immediately rush out to develop a dating course or write a cookbook and expect to become successful. Start small by individually helping people whose problems you can solve. Build your experience and learn what people’s biggest challenges are within your niche. Then you can move up to creating a low-cost blog to start reaching a wider audience outside of just friends and family. Keep focusing on providing value, building your rapport, and keeping close track of what you’re learning as you progress. Only then, once you’ve proven that there is indeed a specific need that you can (and want to) solve, should you invest in scaling to a larger audience. What’s more is that this can all be done in a matter of days, weeks, or months based on your level of expertise, strategic relationships, and amount of time you have to dedicate to your business.

Is it important to develop leadership skills even if you are a solo entrepreneur?

Absolutely. Regardless of what type of business you’re starting, your clients and customers are going to look to you for leadership with the problem they’ve hired you to solve or have bought from you.

How have your leadership skills helped you get to where you are today?

My first really immersive experience building my leadership skills was during college when I became the president of my fraternity. The most impactful lesson that’s stuck with me throughout the years has been the importance of remaining calm during a crisis. Having wild, unpredictable reactions never helps anybody. That experience has taught me to not be reactionary within my business, to always force myself to evaluate situations with as much objectivity as possible, and to not be afraid to ask the people I work with for their opinions on how to approach complex scenarios.

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