PMC 2025: The Spirit of Massachusetts, the Best of America, & Collaboration on Steroids!

By Craig Hall Underwood, August 22, 2025

On Sunday morning, August 3rd, at 3:45 a.m., I stood in the pre-dawn glow watching hundreds of volunteers serve breakfast to thousands of riders before the final leg of the Pan-Mass Challenge (PMC). I had an epiphany. This scene — and the entire weekend’s event, where I completed my 11th PMC riding 170 miles from Wellesley to Bourne on Saturday and then on to Provincetown — revealed something powerful: The PMC embodies the Spirit of Massachusetts and the very Best of America, at a time when we desperately need both.

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CHU Recommends: The Experimentation Machine, by Jeff Bussgang

 

I am fortunate to have known Jeff Bussgang for over 25 years and can honestly say that he is the perfect person to have written this book (and perfect is not a word I use often!).

Jeff studied AI in the late 80’s as a computer science student at Harvard (And before you call BS on that statement, realize that the term Artificial Intelligence was coined by in 1955 by computer pioneer John McCarthy!); was a very early stage “joiner” at Open Markets, an internet commerce infrastructure leader in the early Web 1.0 days; the Co-Founder UPromise; and currently serves as a Co-Founder and Partner at Flybridge Venture Capital and a Senior Lecturer/ Professor at Harvard Business School, where he formerly was an (maybe the first?) Entrepreneur in Residence.  Flybridge is currently investing a fund 100% dedicated to AI start-ups and HBS now requires all students to use AI in most, if not all, classes.   Jeff is also one of the nicest (not a word often associated with VC’s),charitable and by far the most connected person I know.  Despite how incredibly busy he is, Jeff somehow always seems available to take my call!

Leaders far more qualified than I have written glowing reviews of The Experimentation Machine, including:

Eric Ries, author of The Lean Startup: “A Perfect Guide for AI-era founders

and Reid Hoffman, Co-Founder of LinkedIn and Inflection AI “A valuable, empowering read for entrepreneurs everywhere.”

I would take Hoffman’s praise a step further and recommend The Experimentation Machine as an important read, not only for AI Founders, but also for AI startup joiners/ followers and the general public, as it has become clear to me that everyone will either be affected by AI or benefit from using it.  In addition to learning a lot about AI and how “10X” founders are using AI to create next-generation businesses, you will learn about building a business plan, finding a profitable product market fit, and valuing early-stage enterprises.

If you want to immediately add some “AI Intellectual Capital,”  I recommend first reading Bussgang’s Appendix A “Prompt Tips and Examples,”  which contains a mini-course in prompt engineering, and D “AI Apps Unwrapped,”  which contains a list of dozens of AI tools by usage category (e.g. “General Assistance,” “Get Creative,” and “Have Fun.”).

I have recommended this book to hundreds of friends, followers, clients, and colleagues and am confident that you will benefit from reading (or listening to the audiobook in Jeff’s own – not his AI – voice).  My only suggestion for Jeff is to create a companion PDF for the audiobook, which could easily be done by using the PowerPoint slides he shared at the recent HBS book launch reception for The Experimentation Machine.

CHU

Net/ Summary:

If it feels like AI came out of nowhere, is suddenly everywhere, and you somehow missed the bus—you’re right about the first two, and dead wrong about the third. While AI adoption has skyrocketed—faster than any technology in modern history—actual usage still varies widely by industry, age, and education. I’ve recently taken a deep dive into AI’s capabilities, and I’m here to tell you: it’s not too late to catch up. You can start using these powerful tools today.

The best way to learn AI is to use it. Tools like ChatGPT, Microsoft Copilot, and my favorite, Google Gemini, offer free versions and premium options (around $20/month) with expanded capabilities. The key is not to treat them like Google search boxes, but like smart collaborators.

Give AI context. Tell it who you are (e.g., “a nonprofit strategist”), how you’ll use the output (e.g., “to draft a fundraising plan”), and what tone you prefer (e.g., “professional but conversational”). Upload background documents and relevant data. Ask it to help you brainstorm, reword emails, rewrite resumes, analyze data, or even generate cartoons from photos.

Don’t know where to begin? Try:

  • Editing a recent cover letter and resume (include the job description in your uploads)
  • Rewriting an important email in a friendlier tone
  • Summarizing a report
  • Asking how AI could help with a work or personal challenge

I highly recommend reading the books The AI Driven Leader, by Geoff Woods and The Experimentation Machine, by my friend Jeff Bussgang.  It you want to jump start your learning from these books, consider reading Wood’s last Chapter 14 “”Go from 0 to 1: The Simple Path to Deliver Value with AI” and the Appendix “Prompt Library”   and Bussgang’s Appendix A “Prompt Tips and Examples” and D “AI Apps Unwrapped”  which contains a list of dozens of AI tools by usage category (e.g. “General Assistance,” “Get Creative,” and “Have Fun.” ) first.  There are also dozens of online courses on how to effectively and efficiently use AI, including Google’s AI Prompt Engineering Course on Coursera or – if you are as impatient as I – first watch the YouTube video “Google’s 9 Hour AI Prompt engineering Course in 20 Minutes.

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Summary/ Net: 1. Keep smart, fight Russian disinformation and propaganda, and share with others. 2. Contribute to Operation Support the Front Lines in Free Ukraine. 3. Patronize Ukrainian artists and businesses. 4. Help Ukrainian refugees. 5. Write elected officials and candidates.

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5 “NO REGRETS” ACTIONS YOU CAN TAKE RIGHT NOW TO HELP UKRAINE

Originally Published March 7, 2022 Last Updated March 9, 2022

This is a photo of Yaroslav Mudriy [for critical security concerns, his real name cannot be revealed at this time], with his niece Mariya and sister-in-law Olena taken in the strikingly beautiful 1600+ years old city of Kyiv when I visited them in 2006. Yaroslav and his brother Oleksa Dovbush [same security concerns] moved to Ukraine 31 and 30 years ago, respectively, and both became successful U.S. investors and entrepreneurs.  In addition to Mariya (who is currently a first-year student on scholarship at a prominent university in the U.S), Oleksa  & Olena have a 7-year old boy named Romchyk.

Like others in the Western World, I have watched with horror as the news and updates of Putin’s attack on the people of Ukraine unfold.  The good news is that Yaroslav, Oleska and their families are relatively safe as of this writing. (please see the post script below for Yaroslav’s moving account of his harrowing escape from Kyiv at 4 am on the morning of Saturday, February 26th and his 22.5 hour journey to a safe city in Western Ukraine)

I know many are asking, “What can I do to help?”

My article 4 T-Shirts in the Entrepreneurs Closet described the t-shirt slogans of my start-up Sports Loyalty International (SLI).  Our favorite was “No Regrets,” and its meaning was pretty simple:

 Our small team of entrepreneurs committed to each other to never say the words “would have, should have, could have” the morning after losing a sale.  Having a No Regrets mindset means doing your very best, seizing every opportunity, and “leaving it all on the canvas,” to use a boxing metaphor. 

As I struggled to find actions I could take to help Ukraine, I decided to apply the “NO REGRETS” philosophy to help Yaroslav and his fellow Ukrainians. I know I cannot control the outcome of this terrible crisis, but there are at least a few things I can do to try and help right now.   Here are 5 actions we can all take to support Ukraine:

  1. Contribute to organizations providing humanitarian support for Ukrainians still in the country and over 2 million who are now refugees in neighboring countries. Here are two of many opportunities:

  1. Sign The Petition for an International Tribunal to hold Putin accountable for war crimes. A coalition of civil society organizations, including the Ukrainian World Congress, the largest association uniting Ukrainian diaspora worldwide, the Free Ukraine Resistance Movement, and others, have launched a global petition calling for an international tribunal to Putin for the war crimes that are being and have been committed. The petition aims to collect 10 million signatures from across the world to send a strong message of support to all of the Ukrainians on the ground and add still needed pressure on our governments to start the legal proceedings at the ICC.

  1. Write President Biden, your Congressional Representatives and your Governor  asking the US and all states to stop importing Russian oil, increasing the production of US sources of energy and divesting/ stop doing business with all Russian based companies . For those of you concerned about both the economic and environmental impacts of US actions to boycott Russian oil and increase production of US (and other countries’) oil and gas, please read this excellent Washington Post articleHow to Beat Putin, For Real”  by Fareed Zakaria that refutes both of these arguments.

Write President Biden here.  Write your Members of Congress here.  Write your Governor here.

 

  1. Support the dozens of companies who have stopped doing business with and in Russia and stop patronizing the few companies still doing business there. Write their CEOs demanding they join those not profiting from trade with Russia.

 

5. Pray for Ukraine and that Western leaders are taking actions to stop Putin that we are not aware of. For those of us who pray, please pray for the safety of Ukrainians, for the end of this crisis, and that actions are being taken by our leaders confidentially. Although I am not qualified to have an opinion on this, it has been maddeningly frustrating to watch President Zelensky’s pleas for the US and other Western Nation’s air support, including planes and the declaration of a no-fly zone (which 74% of American’s support).  I take some comfort in the hope that our leaders are indeed engaged in actions to defeat Putin’s attack that we are not aware of.  Remember that on May 1, 2011, while President Obama was telling jokes at the annual Washington Correspondent’s Dinner – the raid on Osama bin Laden’s compound was already underway. (please note that this is not meant to suggest that the US or any NATO country are planning an assassination of Putin)

One final action – please share this with others and – for the extroverts among us – download this sign, print a few copies, and ask the local businesses you patronize to post it in their establishments.

Please send me ideas you have for supporting Ukraine to craig@underwoodpartners.com.

Slava Ukraini!

 

PS Here is Yaroslav’s account of his escape from Kyiv and his reasons for staying in his beloved adopted country Ukraine (written in the third person):

On Thursday Feb. 24 — as Kyiv was slammed by Putin’s deadly missile strikes, aerial bombardment, and long-rage artillery shelling — Oleksa and Romchyk left Kyiv by car.  Olena, with four cherished rescued cats, implemented another evasive prepared-plan. Yaroslav’s wife Nataliya actually had left Kyiv by car — along with four beloved rescue dogs and three rescue cats (and meticulously prepared survival equipment & supplies) — a few days before the massive invasion to a smaller city to help her terminally-ill 87 year old Father.

Yaroslav — along with his best-buddy rescue cat Ma’rco — made a firm commitment to stay in Kyiv — even in the event of a Russian invasion.  In fact, for two weeks he was solo-building an improvised “bomb shelter” in a guest bedroom (where Craig, Yaroslav’s best friend at Oxford slept during his week-long visit to Ukraine in 2006).  But, soon after the Russian massive invasion began at 5:16 AM Kyiv-time on Feb. 24, 2022, numerous well-armed, hyper-fit, confident, and cheerful soldiers began to assume combat positions in this 1916 architecturally/historically important building.  Yaroslav on several occasions gave them bags of food from his ample stocks.  (Most residents/neighbors left the building by Thursday afternoon…)

At 2:00 AM Kyiv-time on Saturday Feb. 26, the Ukrainian commander told Yaroslav: “Please leave immediately.  When asked “why?”, he answered: “Because we know, that they know, that we are here.”  Yaroslav left on foot at 4:00 AM with Ma’rco in cat-carrier in his left hand, a heavy backpack, and a bag full of irreplaceable original documents in his right hand.  As he made his 1st step onto the sidewalk, a ferocious firefight began (replete with machine guns, RPGs, and mortars) several hundred yards away behind the facade of one of Ukraine’s finest and oldest universities.

After a few kilometers of walking, and battered by abnormal physical activity for many days and no sleep for 70+ hours, Yaroslav had to stop.  Thankfully, Oleksa arranged for a good American Friend whom he met in the early 1990s, to come and pick Yaroslav up at 7:30 AM — just after Martial Law curfew had ended.  Yaroslav was kindly driven some 15 kilometers to the ring-road, where after a mere 8 minutes he hitched a ride that would take him, 19 hours and 600 kilometers later, away from embattled Kyiv!

Oleksa is adamantly determined to remain in Ukraine.  But, should the situation radically deteriorate, he will –for the sake of Romchyk – evacuate to Poland or Slovakia.  No matter what, Yaroslav is NOT going to leave Ukraine (and 2 months of daily calls/e-mails from the U.S. State Department to “evacuate immediately” simply fell on deaf ears…).

Summary: We drove over 3,000 miles last week from Boston to Atlanta, Jonesboro, Ellenwood, McDonough, Riverdale, Montgomery, Griffin, Lagrange, Oxford and Covington, Georgia and back home.  We travelled south to work door-to-door canvassing to help the Reverend Raphael Warnock and Jon Ossoff win their runoff races to represent Georgia in the US Senate.  The bulk of our time was invested in “curing” rejected ballots – mail-in ballots that had been rejected because the voter didn’t include the requisite ID or the Board of Elections reviewer decided that their signature did not match the one on file.

We realized that voter suppression was not only real, but much more insidious and painful than imagined.  Warnock and Ossoff won because their campaigns and the efforts of the Georgia Democratic Party were far superior to those of the Republicans, and because Stacey Abrams and her 2018 gubernatorial campaign manager Lauren Groh-Wargo provided the strategy and the intellectual, implementational and inspirational leadership to win the Georgia races and  flip the US Senate.  We also experienced the highs and lows of Wednesday, January 6th.  We woke to see data convincing us that both Warnock and Ossoff would win, were moved and inspired by the words and Memorial of Dr. King next to the  Ebenezer Baptist Church and then watched the horrific events unfold at our Nations Capitol throughout the afternoon and evening. As heartbreaking as those images and acts were, we remain optimistic about our future given both the impact of the leadership and work we saw in Georgia and the words of Dr. King who reminds us that “the moral arc of the universe bends slowly, but it bends in the direction of justice.”

 “We came to Georgia to do GOTV work, we were blessed to have the opportunity to do civil rights work.”

The 5 Observations from 8 Days on the Front Lines in Georgia

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