Owner of Drip Sells to Leadpages Without Losing Sight of his Principles

Owner of Drip Sells to Leadpages Without Losing Sight of his Principles

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My guest today is Rob Walling. Rob is a serial entrepreneur that built one of the most successful ecommerce marketing platforms on the market, maybe you’ve heard of it… Drip. We discuss Rob’s early entry into the world of business and how he became a giant in the tech space. He lives by 3 main principles that have guided him on his entrepreneurial journey. He shares why these principles are so important to him and how he came to the conclusion he needed them. Let Rob’s insights help you take a closer look at your own principles and what drives you!

You will learn about:

  • Rob’s early years selling goods to his classmates and what he learned from it.
  • How Rob found his way into the world of coding and software development.
  • How DotnetInvoice started it all.
  • The system Rob developed to keep his companies and his profits growing.
  • The 3 principles Rob looks for in any business endeavor.
  • How Rob found purpose in his work.
  • The purchase of HitTail and how it changed things for Rob.
  • Why Google was a driving force to sell HitTail.
  • Drip’s origin story.
  • The best advice Rob has ever gotten.
  • The decision process for selling Drip.
  • Separating business from emotion and how Rob kept his mind on his goals.
  • Rob’s advice to the listeners.

Today’s guest shows us just how important knowing yourself really is in terms of business success and happiness. Rob Walling has built and sold two successful businesses while sticking to his principles and ensuring he’s getting the dollars he needs to live the life he truly wants. Through hard work, education and self-knowledge (including acknowledging your limitations!), you can achieve the freedom you need when the time comes to exit your business.

Principle Is Principle

It might seem like common sense to say that money matters, and rightly so. However, Rob’s own principles of freedom, purpose, and relationships have enabled him to achieve his business and life goals. Living by his principles got him the principle he needed to back his investments, build his companies and live the life after business he wanted.

Rob learned the value of money at a young age, and discovered his entrepreneurial spirit in eighth grade. He was opportunistic — he saw a market niche he could exploit and went to town. He became a salesman at his school. He would purchase items, marked them up and sell them to his peers. Many entrepreneurs start out in a very similar manner: they have a need that is not being fulfilled and they find a way to fulfill it.

He wanted to be able to help out at home and have the financial freedom to buy the things he wanted. This motivation carried him into his next adventure, and his first big success, by showing him that you can make money if you have the right market niche and the drive to capitalize on it.

Find Your Niche

Rob went out and tried and failed at multiple small businesses after college, but nothing really gained traction until he went back to his roots: he found software that fit a niche market in online invoicing to purchase and grow. He saw the opportunity to do something in a field he understood and was able to get into it without having a ton of capital behind him — he had neither family money to draw from nor an investor funding him.

His main goal here was freedom. He wanted to earn enough money to get by each month without slaving away at something he didn’t enjoy. And, courtesy of his previous experiences, he knew he wasn’t built to work for someone else. Enter the next phase of an entrepreneur’s development: the need to be in control and work for yourself. This is a key component to Rob’s principle of purpose. To live a purpose-filled life, he needed to be in control of what he was doing, where he was going and how he was going to get there.

It’s All About the Journey

Finding your purpose is a journey all on its own. Never mind the hundreds of other little journeys you take alongside it. Most of us haven’t yet discovered what our purpose is, but guess what? That’s part of it, too. You need to try and fail, sometimes repeatedly, to truly figure out what makes you tick.

Rob is very insightful and pays attention to his mental and emotional needs. He takes courses and reads about personality types so he better understands himself and how he functions, both as a business man and on a more personal level. This generates a greater understanding of the types of things that he will enjoy doing in his life and what he will derive satisfaction and fulfillment from.

If you’re unsure what your purpose is, it’s time to start working on it. Read, or listen to audio books, designed to expand your understanding of yourself, your business and your lifestyle. Find out what makes you tick and work to uncover as much information as you can about that so you can better enable yourself to capitalize on those things. With great purpose comes great satisfaction, and it makes the transition out of business a lot easier.

Relish in Your Relations

You may find this has already been happening to you, but if you haven’t, you need to start focusing on developing relationships so you can develop yourself. Having purposeful (to draw on our terms) and genuine relationships in your life build the world around you. This pertains to your business life and your personal life, because neither one can be done alone.

In business, you will have tons of relationships. From the front-line worker to an angel investor, you are bound to develop and need to cultivate specific relationships to be successful. In your personal life, it is rare that we run through life without someone (or someones) by our side to help push us through those particularly difficult emotional and mental hurdles life so lovingly places in our path. Oftentimes for us entrepreneurs, these individuals cross over between our business and personal lives and are able to provide us with key insights and advice.

Getting Principle for Your Principles

Eventually, however, we all need to exit our business. Rob had wonderfully successful exits from both of his biggest businesses by sticking to his principles. He built the financial aspect up enough that not only was he earning enough monthly to live a good life, but he also was able to exit the business without a large concern for his financial well-being after the sale. He ensured he was working in things that kept his interest and spurred him for personal and professional growth, but also made sure that he had a large amount of self-knowledge to have purpose outside of his business so that upon exit he didn’t suddenly crash and burn. And, Rob built relationships within his business that generated lots of buy-in and motivation from his staff, but he also looked after his relationships in his personal life (both friends and family) so that he had amazing people to turn to when he was finished with his businesses to keep his life full and interesting.

Rob recognized the need for professional assistance during the sale process and brought in a trusted lawyer and a really good broker to help him get the type of deal he needed to feel okay with selling his company. As a serial entrepreneur, Rob had less attachment to his business than someone who focused only on one business (their baby) from day one; however, this process is emotional for anyone and Rob is the first to admit that the one thing he didn’t do very well during the sale process was take a step back and relax. He allowed himself to get too tied into what was going on with the sale and stressing himself out with worry and anxiety over making the right choices and ensuring he was getting the right results from the sale.

His best advice here is to trust in your team and learn to calm yourself down during the process because —if you’ve built the quality relationship you need to in order to ensure you have the right people working with and for you — you can potentially damage yourself, your business or your relationships from your unusual and stress-motivated behavior.

So the question he wants you to consider today is: What are your principles?

And the follow-up to that is: Are you living by your principles to ensure maximum success in life, business and life after business?


  1. Rob stuck to his principles whenever he had to make a decision. He was self-aware enough to search his own wants and thoughts and find what he needed. Rob’s principles are freedom, purpose, and relationships. It’s great to see him living his truth.
  2. Rob is a master long-term planner. Nothing he did was done flippantly or hastily. He always researched his next move and carefully made the right choice for him and his business.
  3. Selling a business is stressful. Rob did a remarkable job explaining the turmoil and struggle that comes with the negotiating process. He also made a good argument for having a top-notch financial team at your disposal.

Links and Resources

Rob’s Website and Blog
Rob on LinkedIn
Start Small, Stay Small
Startups For the Rest of Us Podcast
Zen Founder Podcast

About Rob:

Rob is a serial startup founder, angel investor, and author. He has sold a few companies, wrote a bestselling book, been interviewed in the Wall Street Journal, Forbes and Inc., received a Wikipedia page, and reached hundreds of thousands of people through hundreds of interviews, talks, books and articles.