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1/28/23 – The Itinerant Weekly – #33

 Welcome back, polymaths! 

Here’s your dose of brain food.


How startups can land a second meeting with a corporate partner; new tool for identifying business opportunities; tech earnings slump – finally; smaller VC funds generally have stronger returns; even startups with material runway likely won’t grow in to their valuations; investors eye cross-border boutique hotel investments; healthcare venture ecosystem is being impacted by the tech market correction – just like everyone else; U.S. Government established the Office of the Special Envoy for Critical and Emerging Technologies; a deep dive into the so-called ‘largest con in the world’; and the reality of psychology and how we’re programmed to deceive ourselves.

Stay curious this week.

Let’s go!




As always, please give me feedback. Which area this week was your favorite? Which did you like the least? What do you want more or less of in general? Please let me know.

Email me, leave a comment, tweet / cast / or clout @BenErsing and put #TheItinerant at the end so I can find it.

The Itinerant Weekly is available on Diamond,, Medium and now


Article [5 min] – How Startups Can Land a Second Meeting with a Corporate Partner

#Entrepreneurship #Partnerships #CorporateInnovation #HBR

  • A good performance during that first interaction is essential. There are usually no second chances. But how can start-ups gain that critical second meeting? (1) Have clear, yet flexible goals. (2) Address existing problems and needs. (3) Address ease of integration and collaboration. (4) Present use cases and new value propositions. (5) Assemble the right team and have them present in the meeting

Product/Tool [n/a] – Subreddit Stats - statistics for every subreddit

#Entrepreneurship #SideHustling #Ideation

  • If you’re a founder, aspiring founder, or intentional tinkerer and side-hustler, check out this tool which tracks subreddit topic interest over time. Potentially helpful if you’re looking for consumer product opportunities.


Article [2 min] – Microsoft (MSFT) Kicks Off Tech Earnings Set for Biggest Slump Since 2016

#MacroEconomics #Recession

  • While Wall Street analysts have been cutting earnings projections for months (leading to the market price correction), corporate tech earnings forecasts finally begin to adjust as widespread layoffs heat up. Just three months ago Wall Street expected flat earnings (i.e., no growth/decline), and sentiment has dropped quickly. Tech valuations are still far from cheap despite last year’s 33% tumble in the Nasdaq 100. The gauge is priced at about 21 times profits projected over the next 12 months, compared with an average of 20.5 for the past decade, and further estimate cuts would only make it look more expensive.


Article [4 min] – Micro-VC — Smaller is better, but the math is still really hard

#VentureCapital #FundStrategy #AlternativeInvestments

  • Smaller funds have better returns, mostly because they’re easier to deploy and require less overhead to manage. Still – its not easy.

Article [2 min] –  Even startups with lots of runway probably can't grow into those sky-high valuations

#VentureCapital #AlternativeInvestments

  • If you’ve made any personal start-up investments in the last 12-24 months, there’s a good chance you’ll experience a so-called ‘down-round’ in the coming quarters. Many will come back to you as an investor at a previous, higher valuation first, hoping you’ll pull the trigger and dish out more cash. Every situation is unique, but be thoughtful and do some quick math first to assess whether you think they’ll be able to grow into the valuation ever, or if a down round is likely inevitable. If its likely inevitable, you may want to wait and invest later, at a lower valuation – if you still strongly believe in the business fundamentals and long term potential.     


Article [5 min] – First-time Buyers Account for 16% of Global Hotel Investment Volume in 2022 According to JLL

#GlobalRealEstate #AlternativeInvestments #Global #BoutiqueHotels

  • Despite global economic volatility, labor shortages and supply chain disruptions, the global lodging industry was largely boosted by leisure demand and notable international tourism events. An estimated 700 million tourists traveled during the first three quarters of 2022, an increase of 133% compared to the same period in 2021. More and more first-time-buyers are investing in cross-border boutique hotels. If you and your family enjoy global travel, and you want a pied-a-terre or two but don’t want to own 100% of a house that will just sit there when you’re not using it, one option you could consider (that I’ve been digging into for a while) is to be a minority investor in a boutique hotel. Careful selection is required as the industry can be opaque and there are many bad actors, but if selected correctly, my early findings suggest it can make financial and personal sense in some cases.  


Article [5 min] –  Tech slump is testing even healthcare, the most resilient of sectors

#GlobalHealth&Wellness #HealthcareEconomics #Startups

  • Most digital health and device companies aren't expecting revenue pressure. The same goes for pharmaceuticals with FDA-approved drugs. "Healthcare spend is mostly fixed," as one investor told me this week. The objective for these companies has always been to capture a bigger slice of the enormous "fixed" pie, which in 2021 accounted for over 18% of US GDP. Nevertheless buzzwords like "margin expansion" and "path to profitability" were the phrases du jour heard from established public and VC-backed companies alike…. It turns out that no matter how resilient healthcare businesses may be to the economy's cycles, they're still subject to market valuations. And those valuations got out of hand for tech-enabled companies during the tail end of the boom cycle…  a good deal of consolidation ahead in part because there are now "too many" solutions on the market, and employers are reluctant to add more offerings as they look to manage their costs.


Article [3 min] – US Establishes the Office of the Special Envoy for Critical and Emerging Technology

#TransformativeTechnologies  #USGovernment

  • U.S. Department of State opens the Office of the Special Envoy for Critical and Emerging Technology. It will provide a center of expertise and energy to focus on emerging technologies that will transform our societies, economies, and security—including biotechnology, advanced computing, artificial intelligence, and quantum information technologies. Secretary Blinken established the office as part of the wider modernization agenda because the constellation of critical and emerging technologies reshaping the world is now an integral part of the conduct of U.S. foreign policy and diplomacy.

Article [30 min] –  How The World’s 3rd Richest Man Is Pulling The Largest Con In Corporate History

#Entertainment #Fraud #Con #AdaniGroup

  • This makes the FTX scandal look like child’s play…Findings of a 2-year investigation present evidence that the INR 17.8 trillion (U.S. $218 billion) Indian conglomerate Adani Group has engaged in a brazen stock manipulation and accounting fraud scheme over the course of decades. If it is quite remarkable – and certainly entertaining to read. Someone is going to make a movie


Article [5 min] – 10 Things You Don't Know about Yourself

#PersonalGrowth #Psychology

  • You probably do not understand yourself as well as you think you do. (1) Your Perspective on yourself is distorted. (2) your true motives are often a complete mystery to you. (3) outward appearances tell people a lot about you. (4) gaining distance from yourself can help you know yourself better. (5) we too often think we are better at something than we are. (6) people who tear themselves down experience setbacks more frequently…