20 Entrepreneurship Lessons from World's Top Business Thinkers, CEOs and VCs

07/20/2016 11:03 am ET Updated Jul 21, 2017

Ray Wang, bestselling author and CEO and founder of Constellation Research, and I are greatly fortunate and have the privilege of speaking with some of the best and brightest business leaders and entrepreneurs on our weekly show called DisrupTV. Our guests include Fortune 1,000 CXOs, startup CEOs, venture capitalists, and technology and media thought leaders. Our goals is to identify business, leadership and innovation disruptive macro and micro trends and to give our audiences direct access to the most influential change agents in the world.

Here are 20 entrepreneurship lessons that we learned from some of our recent DisrupTV guests:

Anshu Sharma is Executive in Residence and Venture Partner at Storm Ventures where he is focused on building software companies that leverage the power of SaaS, mobile and cloud by working with closely with early stage entrepreneurs. His motto is "your company is an App now" - as he envisions industries ranging from healthcare to banking being redefined by everything as a service delivered on the supercomputer in our pockets.

1. Blogging is a very lonely experience, but worth doing. Sharma is most famous for writing a post about the 'Stack Fallacy' - a false belief that the higher you go up the technology stack, the easier it is to build solutions. Sharma notes that after running 250 blogs, it was this post that described why big companies fail to innovate that hugely propelled his thought leadership throughout the industry.

2. The future of apps should be better apps. Sharma invites companies and app developers to focus on improving the functionality and user experience of mobile apps. "We can fix the gaps in apps so that they become seamless and easy to use," said Sharma.

3. The most important startup key performance indicator is 'number of users'. It's never been a better time to be a SaaS company. If you really have real usage and adoption, then your company will grow and survive. What good companies obsesses about is number of user logins, customer objects, and usage. Strong VCs look at product demos and research real product usage trends. The user adoption curve will be far ahead of the product revenue curve.


Deb Mills-Scofield - Partner at Glengary Venture Capital, Business Innovation & Strategy Expert and Harvard Business Review blogger. Deb Mills-Scofield helps companies create and implement actionable, adaptable, measurable, and profitable innovation-based strategic plans. Deb has been doing this successfully for 25+ years with service, manufacturing, and high-technology companies from large global companies to early-stage. She has also done some carve-outs, start-ups and start-downs.

4. Doing well, and doing good, are not mutually exclusive, but mutually reinforcing. If you are not doing well, you don't the money to keep doing good. Is your company doing the work for the right reasons - can it create meaning and money, purpose and profit?

5. Customers want meaning, value and purpose for them. If you don't have your value proposition done, you don't need to worry about the business model. This means deliver value in the context and constraints of the customer, not what you would like it to be. This means understanding your customer's customer needs from their perspective.

6. Humble confidence is key to success. Humble companies ask for help and they give their employees the freedom to fail and try stuff. Companies that trust their employees will be more innovative. Business leaders must walk the talk and give their employees the freedom to experiment. According to Scofield, good leaders take all of the blame and none of the credit. Good leaders also promote and celebrate cross-collaboration across the lines-of-business.

7. The 'no shmucks' policy. The first thing that Scofield's VC firm looks for is matching the startup's domain expertise with firm's partners. The second is the people. No investing in jerks, no matter how good the idea or business model.

8. When you don't ask, the answer is no. Scofield encourages people to consider asking for help or well-deserved promotions or pay raises. She also encourages change agents to ask for forgiveness, not permission. Throughout her career, Scofield defined her work responsibilities and actively led her career direction.

Alex Osterwalder - Co-Founder of Strategyzer, Bestselling Author, and Thinkers50 2016 Most Influential Business Management Thinker. Dr. Osterwalder's twitter bio it reads: "Won't rest until executives and entrepreneurs operate like surgeons!" Strategyzer helps companies build better business models with practical tools to help businesses better understand their customers, design better value propositions and find the right business models. Osterwalder is also an international bestselling author with books translated in 40 languages and sold over million copies. In fact over 5 million people have downloaded the Business Model Canvas.

9. Why is it harder for larger companies to innovate? Organizational structures today are designed to execute a known and proven business models. But trying to do something differently, something outside of your execution engine, is hard. An ambidextrous culture - one that is focused on both execution and innovation - is required to minimize exposure to disruption. We are at a point that companies need to be redesigned. You cannot reinvent yourself by cutting costs - some companies are dying efficiently based on continuous cost cutting programs. Company reinventions require active board involvement and a dedicated business executive - a chief innovation officer.

10. Business models are like yogurt - they all have an expiration date. Companies have to invest time and energy to combat against learning decay. Companies also have to invest in best-in-class tools and technologies to stay relevant. Acceptance and usage of business model tools began in the startups and then emerged in industries that had accelerated business model expiration. Today, chief technology officers (CTOs) and chief marketing officers (CMOs) are leading business model innovation programs within larger corporations.

11. Innovation is not expensive. Technology R&D is expensive (technology decision is about can we do it?). Innovation answers a different question: 'should we do it?' Innovation is not expensive in the early stages but it does get expensive when it is time to scale. Companies need to recruit and empower a chief innovation officer (CIO) or corporate entrepreneur in order to survive. 52% of the Fortune 500 companies have disappeared since the year 2000.

12. Today, most companies use PowerPoint and Excel to manage their company's strategy. Businesses need to utilize more sophisticated tools to manage strategy. Innovators need to maintain a long-term vision but also be able to manage their tactical and operational assignments with tools that help improve execution velocity and business outcomes by leveraging systems, methods and structures.

13. Business is not about making money, business is about creating value for customers. Money is simply a metric to measure success. If you create value for customers with a great business model, then the money will come on its own.

Clara Shih is CEO and founder of Hearsay Social, whose predictive analytics technology helps salespeople reach out to clients at the right time with the right message. Shih is the author of New York Times-featured best-seller, The Facebook Era and her new book The Social Business Imperative. Shih has been named one of Fortune's "Most Powerful Women Entrepreneurs," Fast Company's "Most Influential People in Technology," BusinessWeek's "Top Young Entrepreneurs," and both Fortune's and Ad Age's "40 Under 40." Shih was also named a "Young Global Leader" by World Economic Forum, Shih is a member of the Starbucks board of directors and previously served in a variety of technical, product, and marketing roles at Google, Microsoft, and Salesforce.com.

14. Social and digital is a board room issue. Most companies have not seen wholesale transformation results from their social networking activities because they have delegated this work to interns and junior staff. This is a huge mistake. Social and digital have become too strategic and important to completely delegate. CEOs, board of directors and senior management have to personally take responsibility to both understand and apply and determine the strategy for digital to go beyond marketing and communications. They must incorporate a digital strategy into their core business model.

15. The constantly connected customer is disruptive traditional businesses. The always connected customer is more loyal to companies that are always engaged and frequently engaged. The smartphone and mobile and social revolution has created a digital divide for companies that have yet developed a business model that enables them to be always-on and always connected.

16. Business leaders must better understand the impact and experience of social networking. CEOs must understand how their customers and employees experience the world. Even if the CEO does not have a social presence, they must understand emerging social technologies and engagement models. Shih's new book 'The Social Business Imperative' very strongly articulates the importance of business leaders understanding the constantly connected, mobile and social stakeholders - customers, employees and partners.

Seth Godin is the author of eighteen international bestsellers that have been translated into over 35 languages, and have changed the way people think about marketing and work. For a long time, Unleashing the Ideavirus was the most popular ebook ever published, and Purple Cow is the bestselling marketing book of the decade.

17. We live in a permission economy. So how does a business lead in the permission economy. Permission is the privilege of talking to people who want to talk to you, and not because it's important to you. It is about being missed if you don't show up. Are you doing something worth following? If you're not, then you're not leading.

18. The world is changing. What does it mean to live in a world that is changing? The key element to being a CIO or a CMO is to be a chief learning officer (CLO). To be an artisan - not a craftsman, because a craftsman does the something again and again - is to learn to do it different the next time, to do it better the next time. To be an artisan, you have to be willing to listen and learn. What it means to learn is to fail

Gary Veynerchuk is the CEO of @vaynermedia and bestselling author of Crush IT, The Thank You Economy, Jab Jab, Jab Right Hook and #AskGaryVee. Gary also currently hosts The #AskGaryVee Show, a way of providing as much value as possible by taking questions about social media, entrepreneurship, startups, and family businesses and giving his answers based on a lifetime of building successful, multi-million dollar companies. Gary is also one of the best follows on Twitter at @garyvee.

19. Your word is bond. Your honor is everything.

20. Be patient and invest in your future. Try to live your life in a way that you actually realize that you'll be around in five years. Do the right thing, for the right reasons, and most importantly be patient.

Ray and I have completed 25 shows and interviewed over 80 guests on DisrupTV. We hope you can join us every Friday at 11AM PT/2PM ET to learn more from the best and brightest business, leadership and innovation leaders in the world. You can follow us on Twitter at @DisrupTVShow.