6 Inspiring Business Lessons I Learned From Carly Strife and Seth Godin at ‘Small Biz, Big Things’

Last week, I joined some 250 entrepreneurs and small business owners at “Small Biz, Big Things” for a wonderful evening of learning and sharing with Barkbox co-founder Carly Strife and author/speaker Seth Godin. SmallBizTechnology’s own Ramon Ray kicked off the event, which was sponsored by Infusionsoft, by firing up the crowd. He assured us that we all share many of the same struggles, oscillating somewhere between barely surviving and thriving as a small business. He promised that the evening would yield answers to some of our most pressing questions about small business success, and it did!

Carly Strife, co-founder of Barkbox, spoke first, sharing with us the journey that brought her to her current position. Her career started at consultancy Deloitte where, despite being successful, the work simply was not personally rewarding. She surrounded herself with people whose passion she admired and those that shared a common vision for success. This landed her an opportunity at the start-up Uber, where she helped them become the market-dominating transportation app.

Although this was exactly the type of job she thought she had wanted, Ms. Strife made a very significant realization: “I simply wasn’t passionate about the taxi and transportation industry and this limited what I could contribute.” Armed with this self-awareness, she co-founded a new company, one that focused on her true love: her dogs. Since that day, New York-based Barkbox has become a phenomenal success, slated to achieve $25 million in revenue in its third year, and spinning off a number of equally successful companion companies.

The three main lessons I took away from Ms. Strife were:

  • If you want to do something, go do it. Despite being successful in two significant roles prior to founding Barkbox, Ms. Strife realized that something was missing and only she had the power to pursue it. Working on something that doesn’t fulfill you ultimately undermines your job satisfaction and limits your professional success. It’s scary to make a dramatic change, but the alternative should be scarier.
  • Pursue your passion. In addition to providing greater personal satisfaction by doing something enjoyable, a company (or individual) that is able to focus on a single passion-driven cause can operate with “laser like focus.” When you have such clarity of purpose things are either aligned or they are not. This avoids much ambiguity and costly distractions.
  • Don’t be afraid to try lots of things along the way. While currently analytics and ROI analysis of marketing campaigns play a much bigger role than in the start up days of Barkbox, things were not always so. Ms. Strife encourages entrepreneurs to try many different marketing approaches, not being afraid to see what sticks. If you dismiss too many ideas because they might not work, you will miss some surprising successes.

Celebrated author and speaker, Seth Godin, was up next. His broad business acumen spans permission marketing, sales, branding, customer acquisition and retention to name a few. Mr. Godin has an immense talent for cutting through the clutter and identifying common sense wisdom that most of us miss because we’re too “down in the weeds” of running a business.

I learned enough to fill several pages during this great evening, but my key takeaways from Mr. Godin were:

  • ”If you are selling to everyone, you are selling to no one.” In an economy that has replaced retail shelf scarcity with nearly limitless choice, it is important to properly identify your ideal customer and find more with similar traits. He suggests you sell to the “weird,” those on the fringe, as they are more likely to have problems to solve and to want to belong to a community of like-minded customers of a common brand. There’s also nothing wrong with not trying to sell everything and instead curating “only the best” (as defined by your unique customers’ needs).
  • ”The world’s job is not to hear the story you want to tell, but for you to tell the story the world is ready to hear.” Many entrepreneurs are convinced they have a good or service that will sell and end up disappointed. This often results from companies offering a square peg solution for a customer’s round hole problem. The best companies figure out what story their ideal customers are telling themselves about why they are customers, ensuring the company’s story (or offering) is perfectly in sync.
  • “Targeted spam is still spam.” If you’re spending time and money running marketing efforts that aren’t targeted, you are interrupting your audience. Response rates are typically very low and only huge brands with broad recognition and ability to achieve significant share of voice should attempt interrupt marketing. The rest should focus on permission-based and discovery marketing, providing a suitable offering to those already looking for one.


Mr. Godin left us with perhaps the most important insight of his career: almost all of his key successes were a direct result of, or followed some of his biggest failures and setbacks, reminding us that it’s okay to fail as long as we keep trying and learn from our mistakes. 

If you’d like to see more attendee comments from the event, you can check out the twitter feed  by searching for  #smallbizbigthings. 

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Mario Kroll

Mario is an entertainment industry veteran with extensive executive, managerial, entrepreneurial and hands-on success in marketing, advertising, public relations, social media, customer acquisition, business development, sales management, retail and digital distribution, publishing, general management and operations. Prior to joining the entertainment industry, he was a successful technology and business process improvement consultant for a number of leading financial, technology and consulting firms.

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