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Let me teach you the best of what I know! My blog posts contain the best insights and lessons-learned from my years as a corporate strategist and product management leader in the high tech software industry as well as what I’ve learned in the past three years of starting and running my executive coaching business.

25 Tools I Use To Run A Prosperous Online Coaching Business

What’s great about being a online business owner nowadays is that fantastic software and hardware tools can make life easier, automate tasks and improve the client experience. While I list all the essential tools I use in my business below, don’t let the list overwhelm you! If you are just getting started as a coach, pick a few tools to adopt at first. Add more as you grow and scale your business. That’s what I did!

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What I’ve Learned in Two Years of Entrepreneurship


This article marks the second full year of my being a business owner. Before that, I worked in the corporate world for my entire adult life.

I always considered myself a business savvy person. I read the Wall Street Journal and dreamed of working on Wall Street from the time I was in 5th grade (strange, I know!). I ended up, luckily, not on Wall St., but instead working in the world of High Tech. My roles had businessy titles like Financial Analyst, Business Development Analyst, Product Manager, Principal Product Planner, Director of Business Planning and the like. I worked on acquisitions, product planning, innovation and strategy projects. I used to think that I knew how businesses worked and how to build products customers would enjoy.

I figured that when it came time to do my own thing, I'd have a pretty easy time of it. After all, with no one else to slow me down, I should be able to run wild with my ideas and make them happen! Right? I always imaged that running my business would easier than working for a big company. It could be simple, and I would get to call all the shots. I couldn't have been more wrong!

Running a business, even as a solo-preneur or freelancer, is hard. It doesn't matter if you were a rainmaker at a large company there is nothing that compares with the challenges of doing your own thing.

In spite of all these problems, millions of people in the USA alone venture to run their businesses. What is it that draws people to something that is so difficult? The benefits - the lure of freedom and autonomy - as well as the chance to create something that is only in your mind's eye, is very tempting.

Two years ago I took my leap from corporate worker to entrepreneur. Actually, before that, I took the leap to being a world traveler....then leaped to start my business. I expected small challenges along the way, but nothing major. What actually happened was completely different than my expectations.

Now, looking back, I'm glad I didn't know how much effort it would take to get where I am today (which is still not sunshine and unicorns). Yet, I'm glad I did it. I wouldn't trade the experience for anything. I've become a stronger and more capable human being along the way. I'm also far more empathetic to the struggles of people who are trying create something from scratch.

Here are the essential lessons I've learned in the past two years.

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Being An Authentic Entrepreneur

Being An Authentic Entrepreneur

Up until January 2015, I was either a child, a student, an employee or a traveler.

Zeroing in on the times when I was earning a paycheck, I always relied on someone else setting the rules of engagement, defining how work was to be done and gratefully accepted the paycheck (and bonuses, and stock grants) I would be handed every now and then.

My list of jobs has included: lifeguard at my high school, hawking my class notes to other students for $20 a class (legally!), working in the accounting department of a global airline (in midtown Manhattan), setting up offshore funds for uber-wealthy people at Merrill Lynch and finally, for almost 14 years: strategizing, creating and dreaming up the future in a variety of product planning, product management and marketing roles at Microsoft.

In all of the above cases, someone else handed me a paycheck. Then, I left it all behind and backpacked the world with my wife for over a year, during which time I had zero income.

Since 2015, things have been different. I’ve been doing my own thing. I thought I would fit right into the masses of entrepreneurs out there. What I’ve discovered is very different.

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