Pattern Matching, Venture, Investment, Future of Works, and Change - with Guest Villi Iltchev - 178

Managing Director and Partner, Two Sigma Ventures - Villi Iltchev This week Villi Itchev joins Mike to discuss diversity in experience, investment, entrepreneurship, remote work, and lessons learned.  Villi has a multi-fadeted background to include: investment banking with Merrill Lynch, mergers and acquisition with Salesforce, an executive with Lifelock, and head of strategy with Box.  Questions Discussed How does Villi's background influence his approach to investment and research? How have his experiences rounded out his thinking? How does venture continue to innovate and transform? Why is it a great time to be a founder? What are some common misconceptions around investment? How will venture continue to evolve? What options are there for various types of investment? Why do we get drawn into the idea that we need to take on funding to build out to scale, or I'm less than? How will the future of remote work impact organization growth & culture? What inspired Villi's post on ARR being a vanity metric? How do you see the landscape of technology & software evolving over the next 15 years? Key Takeaways Massive transportation within venture.  The competitive nature of venture is commoditizing the asset class.  A data oriented approach is required. The ones that are standing still (just like any industry) are being marginalized  It's a great time to be a founder - it takes little investment to get started and you can make a lot of progress on your own prior to raising capital. There are an abundance of capital sources with different risk profiles. Best way to get started is family & friends. After you make progress start to look at traditional Angel & Seed financing - be honest with yourself about the type of company you are building. There are plenty of opportunities to build companies. There is nothing shameful in building something that will not grow at venture scale. Think about how Mailchimp started - small ambition, focused solution to an email template problem, that grew into something greater than expected. Start building, start playing, start dreaming - see where it takes you - chase your dream. It's a lot easier to get inspired when you interact with people who have a common interest - leverage your communities, networks, and the resources that are available. Shortage of talent, high demand for technology globally, will lead to a shift in remote work, and create opportunities for growth - the world is becoming smaller. Remote work will allow technology to spread much further. Bookings over ARR - a question you can ask - is your ACV (annual contract value) growing or declining?   Performance is measured by bookings growth. The last 20 years - we put success on the shoulders of the customer. We transferred costs. This shifted to the vendor being responsible for success, as payments shifted to overtime vs upfront. Cloud & SaaS changed the landscape of adoption Next 20 years - the software will make us better at our jobs. What does the next salesforce look like?  It will be about making the end-user better, within each core application. The intelligence will amplify capabilities. Show Links @villi on twitter [email protected] Villi on ARR vs Bookings Thank You  Please send listener questions and feedback to [email protected] or contact us directly on twitter, facebook or LinkedIn. This podcast is brought to you by Catalyst Sale - you can learn more about Catalyst Sale, and the products and services we provide via the following links. Growth Acceleration - Plateau Breakthrough Product Market Fit Demystify Sales - the course