Square One: Conversations with the Best in Business

This week we're talking concepts! It was awesome having Shaan Puri, Former CEO of Bebo on the podcast to chat through a number of them. Shaan and I go way back - we went to Duke together; since then we've formed a tight knit friendship as we've both gone through a number of different startup experiences as investors and operators. After selling his latest company to Twitch, Shaan set out on a host of projects: a podcast that has 2M+ downloads, a $3M rolling fund to invest in startups, an online course and a few other ventures.  In this conversation, we dug into a bunch of concepts and frameworks both Shaan and I have learned over the years. A few of my favorites included: (1) how to pack 4 years of experience in 1, (2) knowing when to shut a project down, (3) the challenges in a business as a function of the CEO's psychology, (4) a 5 part framework for change, (5) how to get "unstuck" and (6) a 2x2 for startup ideas. This one was a blast; Shaan's an idea machine.  Visit his personal site at www.shaanpuri.com to learn more about his projects / ventures. 

This week it was awesome to dive deep into the future of e-commerce and shipping in India with Saahil Goel, Founder and CEO of Shiprocket. Shiprocket is the fastest growing e-commerce solution in India today; COVID has accelerated the business significantly and Shiprocket is shipping over 3 million packages a month now. This conversation was particularly interesting because it was targeted on the Indian market - a low trust consumer economy filled with micro transactions fulfilled by cash. Saahil gave a thoughtful perspective on how to increase transaction trust and why bringing transparency to checkout is the key unlock for mom and pop businesses in India. We touched on a number of interesting concepts: (1) first and foremost - the steps of an e-commerce transaction, (2) focusing on trust in the transaction, (3) building out an ecosystem of partners / integrations and taking a Shopify approach, (4) why post checkout is where loyalty begins for SMBs and (5) building a hyper growth company in India.

This week it was awesome to dive deep into the future of e-commerce with Michael Mayer, Founder and CEO of Bottomless. Bottomless is an intelligent subscription - instead of getting shipments on a set schedule, you get shipments based on usage. This is a fundamental unlock/new insight: Michael believes that our current e-commerce infrastructure models Internet 1.0. Bottomless is the next wave of how we take offline information, online into an organized intelligent schema and subsequently use information technology to move up the s-curve of innovation in this space. In this conversation we dove into a bunch of interesting concepts: (1) why 50% of a company is baked in from the founding moment, (2) how information consumption and focused dissatisfaction is the recipe for original insights, (3) why the unlock in grocery 2.0 is solving an information problem, (4) the characteristics of products that are good candidates for automatic reordering and the byproducts for privacy when a company like Bottomless succeeds at scale.

Since the pandemic, over 100,000 students have skipped filling out financial aid and lower cost local institutions are seeing significant enrollment decline. This is exactly why we need 2.0 institutions that are working towards incentive alignment in education. This week, I dove deep into this topic with Ruben Harris, Founder and CEO of Career Karma. Career Karma simply put is Tripadvisor for your career - it's a managed marketplace focused on connecting high potential individuals with the right skills accelerators to help them harness their potential. In this conversation we talked about a number of topics: (1) unbundling higher education, (2) why Ruben is bearish on resumes and credentialing, (3) how the job market today mirrors the free agency process in sports, (4) how to unlock organic distribution - CK pumps over 700 pieces of unique content in addition to user generated content every month, (5) his early DMs with Balaji Srinivasan (former CTO, Coinbase) on how to break into tech / ultimately building a product for himself and (6) the recent Harvard Business School Case Study on CK.  We rounded out the conversation with Ruben's entrepreneurship motto and what drives him to build CK. 

This week it was a pleasure to have one of the best and most thoughtful operators in the country join us - Kat Cole, COO and President of North America for Focus Brands. Focus Brands - while unknown to many consumers as a parent company - owns companies that are mainstay language in most American households - Cinnabon, Auntie Anne's, Moe's, Jamba Juice and more. In this conversation we explored two big themes: operating and brand building. We spent the first half unpacking operating principles: (1) how to change mindsets, (2) how to evaluate compelling opportunities, (3) solving for being right vs. being curious, (4) curiosity and humility as the foundation for courage and confidence, (5) possibility vs. positivity filters and unpacked each through examples. In the second half we dove into all things brand - namely, how to build, differentiate and sustain brand. We rounded out the conversation with Kat’s sources of learning and ground truth motto she lives by. This was one of the most knowledge packed conversations we have had and it was fun to have Kat on the show.

Over the last 6 months, without question, one of the most nuanced geopolitical relationships has made it to the forefront of mainstream media. This week we answer the question - what in the world is going on with the US and China. The tech community has taken a very strong perspective on US-China relations and there are a number of complex intertwined issues to unpack. Jacob Helberg is one of the most respected and thoughtful policy experts on this topic. Jacob currently serves as a Senior Advisor at the Stanford University Cyber Policy Center and is an Adjunct Fellow at the Center for Strategic and International Studies (CSIS) where he is writing a forthcoming book on U.S. foreign policy and national security, technology policy and China. Previously Jacob served as a Senior Policy Advisor at Google.  In this conversation we unpacked: (1) whether the US and China are in a Cold War, (2) the TikTok Ban and implications for future Executive Orders, (3) whether US-China relations are fracturing the global internet and (4) the plausibility of re-shoring supply chains.

Tik Tok is one of the most phenomenal consumer stories of all time. Seemingly coming out of nowhere, Tik Tok has made an absolute splash in US culture over the past year. But the start of TikTok has a more deep rooted story in the way consumer social products have been evolving over the past decade. In this conversation, I chatted with Turner Novak, General Partner at Gelt VC on all things consumer social. Turner is one of my favorite sources of knowledge on what’s going on in consumer today - he has a deep perspective on international social products and how they translate in the US. In this conversation, we dove deep into the history of consumer social, how TikTok differentiates from other products from a front and back end perspective, what he thinks about Facebook Reels, the impending/potential TikTok-MSFT merger and what are future business models that are byproducts of social he’s excited to see.

Since the start of COVID-19, we have made unprecedented advances in e-commerce. Coined the “great retail acceleration”, US E-Commerce Penetration (as a % of retail sales) grew from 5.5% to 16% from 2009 to 2019. Within 8 weeks post Apr 2020, it grew from 16% to 27%. We have experienced 10 years of e-commerce growth in the last 8 weeks alone. When we think of e-commerce, we often talk about the frontend; both Shopify and Amazon are public tech darlings in the market right now and with good reason. But what we often don’t talk about is the unsexy backend - delivery of e-commerce. It’s why I was so excited to chat with Laura Behrens Wu, Founder and CEO of Shippo. Simply put, Shippo has created the best multicarrier software layer for e-commerce businesses to help streamline the fulfillment process. Laura has raised $60M+ from some of the best investors in the world on the backs of continual explosive growth pre-COVID and post-COVID. We touched on a number of topics in this discussion and Laura intricately explained the nuances of how to think about shipping in a time of explosive growth and operationally how she is leading her business during COVID.

Management principles are some of the easiest topics to discuss, but some of the most challenging to put into practice. The best managers and leaders have an art in making problems so interesting and their solutions so constructive, that everyone wants to get to work and deal with them. This week I was excited to have one of tech’s best thinkers on management principles come on the show. Alex MacCaw, CEO of Clearbit, has recently put out a book titled The Manager’s Handbook - in it he takes his experience as one of the first employees at Twitter, first 20 at Stripe and now leading Clearbit - a company that has raised ~$20M - and translating it to distinct principles and tactics. We discussed a host of concepts in this discussion: (1) how to manage yourself, (2) personal systems of action, (3) failure points, (4) ICs vs. managers, (5) mental and physical health, and (6) leading through COVID. Here’s the link to Manager’s Handbook: https://themanagershandbook.com/?ref=producthunt

The Founders we have had on the show have collectively raised over $1B in venture capital. I’ve heard which investors they enjoy working with, which are most helpful, which are not so helpful but the consistent piece of feedback I have heard is the desire for a more diverse cap table and a more operator centric focus. It’s why I was so excited to chat with Mallun Yen, Founder and GP of Operator Collective this week. Operator Collective was founded on the belief that venture capital concentrated among a homogenous group doesn’t represent where the tech industry is now or where it’s going. Operator Collective has created a new access point for operators from diverse backgrounds; the $50M fund has over 100 LPs, of which 90% are women and 40% are POC. The LP base is filled with many of the best operators in the world having representation from the C-suites of tech’s fastest growth businesses (Stripe, Zoom, Pagerduty, TaskRabbit, Salesforce and more). It was so fun to chat with Mallun. She truly opened my eyes with her thoughtfulness. Around the 50 min mark, after we ended the official podcast, Mallun and I continued the conversation for a few hours. Neither of us knew it was recorded, but I’m so glad it was - we decided to share excerpts from our conversation to continue to add perspective to how we can drive for a more inclusive tech industry. This was one of my favorite episodes I’ve done to date.