Revenue Builders · 8 Oct 2026 · From the week of 5 October
Why Risk Takers Build the Most with Doug Holladay, Author of Rethinking Success
In brief
Doug Holladay, founder and CEO of PathNorth, a Georgetown MBA professor and author of Rethinking Success, returns to the show with hosts John McMahon and John Kaplan to discuss chapters 6 and 7 of his book. The conversation covers the scoreboard people play by without choosing it, the why behind success, how adversity shapes achievement, and how leaders can stay present with suffering. McMahon links a study of valedictorians and the Challenger Sale risk-taker profile to enterprise sellers. The central argument is that people should examine their own why and embrace risk and setbacks before a crisis forces them to.
For founders
- Examine the why behind the scoreboard you are playing by before a crisis forces the question; one of the hosts offered the hypothesis that the earlier people realise this, the better their lives go, and Doug agreed it is a great point.
- Consider planning backward from a chosen end age, as in the Die Broke approach of spending and gifting now rather than living as if you will never die.
- John McMahon's personal practice is to sit for 15 to 20 minutes each morning asking which version of himself is present that day.
- Doug argues that a list of only successes is a narrative, and that showing a record of rejections, as in Johannes Haushofer's CV of Failures, reveals the real path.
- Doug says many people are told to live their passion, but he suggests separating what you must do from what satisfies you and pursuing both, noting that if you are lucky they intersect, though that is not guaranteed.
For revenue leaders
- In the Challenger Sale research as McMahon described it, the risk-taker profile overwhelmingly dominated top performance in complex enterprise software sales, where deals can take nine months to a year.
- Relationship builders who aim to please clients were described as falling behind; Doug added that pushing a client somewhere uncomfortable works only when the client trusts you enough to go there.
- After losing a major client, Doug suggests having each person write two questions for ten minutes before discussing answers, so quieter team members contribute.
- PathNorth runs salons of 35 to 40 people where the questions matter more than the speaker, and Doug says the experience, uncomfortable at first, was predicated on trust.
- One of the hosts suggests that the best leaders recognise suffering in their sellers and others and stay present with it rather than trying to fix it.
What was said 15, most useful first
In a study of 81 high school valedictorians followed for 14 years, students who played it safe by conforming and chasing grades and test scores rarely became standouts in their fields.
John McMahon summarised the Lives of Promise study by Karen Arnold, which followed valedictorians for 14 years after graduation. Per his account, valedictorians were typically playing it safe, conforming to expectations and prioritising high grades and test scores over passionate, specialised pursuits. He said real-world success more often comes from deep specialisation and risk-taking than from broad compliance.
“waar ze 81 hoge schoolvaledictorien trakken voor 14 jaar na de gradatie”
In the Challenger Sale research, the risk-taker profile overwhelmingly dominated top performance in complex enterprise software sales, where a deal can take nine months to a year.
McMahon described five seller groups from The Challenger Sale: relationship builder, hard worker, lone wolf, reactive problem solver and risk-taker. The risk-taker won because they were willing to assertively push back on clients and disrupt conventional thinking. The generalist was least likely to succeed, and relationship builders became the ultimate people-pleasers.
“the risk-taker wins overwhelmingly dominated top performance especially in complex enterprise software sales areas”
PathNorth runs salons of 35 to 40 people where the questions matter more than the speaker, and the conversation becomes uncomfortable before it builds connection.
Doug says PathNorth gathers 35 to 40 people for dinner at someone's home or a club, with a speaker who is secondary to the questions. At a San Francisco salon hosted at the home of the chairman and CEO of Kimpton Group, the question was what your children would say is most important to you. He said it was uncomfortable at first, but within 30 minutes some people were crying and others felt connected for the first time, and that all of it depended on trust.
“It is not about the speaker. It's about the questions.”
After losing a major client, have each person write two questions for ten minutes before discussing answers, because the usual meeting lets the most talkative people set the direction.
Doug's example is a leader with ten direct reports who has just lost their biggest client. In the usual meeting the two people who talk most come up with ideas and the group ends up where it started. Instead, he has everyone take ten minutes to write two questions that would give insight into how the client was lost and how to win them back. He says the quiet person who never speaks contributes, the conversation widens, and the outcomes will be better.
“Let's all take ten minutes Write down 2 questions”
Leaders often chase a scoreboard they never chose, and the measurable how is easy to replace while the why is rarely examined until a setback forces it.
Doug Holladay contrasts the how, meaning everything measurable and easy to replace, with the why, which leaders almost never discuss. He says the how keeps working until it stops, and then the leader has to ask what their why is. The host who raised the scoreboard question offered the hypothesis that the earlier people realise this, the better their lives go, and Doug agreed.
“Ik contrasteel de verschil tussen de hoe en de waarom.”
The best leaders recognise suffering in others and stay present with it rather than trying to fix it, and sharing their own suffering gives people a different view of how long it will last.
One of the hosts draws on the concept of sitting shiva from his father's background, which means being there for another person in their suffering. He says the most authentic leaders share their own suffering in the moment of pain, which gives a different perspective on how long the struggle will last. He describes this as a huge leadership attribute, and Doug agreed.
“I think the greatest leaders I've ever been around are the ones who can recognize suffering”
A financial planner had wealthy clients pick an age they would die and plan backward, spending and gifting now, because clients who never calculated their end date never felt they had enough.
Doug recalled Die Broke by Stephen Pollan and Mark Levine, in which a New York planner asks clients to choose a death age, such as 95, and then works backward. The plan involves spending the money, thanking the people who helped them, and giving to their children while they can enjoy it. Doug said the planner felt most wealthy people never addressed this because they lived in fantasy land about dying.
“they never calculated that we were going to die.”
McMahon sits for 15 to 20 minutes each morning asking which version of himself is present that day, since an earlier self such as a ten-year-old can still drive his reactions.
McMahon says he sits every day for 15 or 20 minutes and asks himself who is there. Sometimes it is a scared ten-year-old, and he and John Kaplan joke about an edgy 13 or 15-year-old version. He says at 63 he can still feel as if events from age ten are happening, and the practice is to recognise which self is showing up before the day unfolds.
“Ik zit elke dag voor 15 of 20 minuten en ik vraag me zelf, wie hier is?”
Johannes Haushofer's CV of Failures lists rejected PhD programmes, unreceived grants and lost interviews, showing that a list of only successes is a narrative rather than a full record.
Doug describes a Princeton professor with a Harvard PhD who published a resume of failures. It lists the PhD programmes he was rejected from, the grants he did not get and the interviews that did not lead to offers. Doug says people need to know that a golden list of achievements does not show the whole path.
“Hij heeft gewoon een failure achter de andere.”
A 1962 study of 400 eminent people found that about 75% grew up in very hard circumstances, which Doug describes as the engine that made them great.
Doug cites the 1962 Cradles of Eminence study by Victor and Mildred Goertzel, which looked at 400 eminent people of the 20th century, including Henry Ford and Louis Armstrong. He says about 75% grew up in utter poverty, hopelessness or a non-nurturing environment, and that this adversity was the very engine that birthed their greatness. He names Howard Schultz and LeBron James as modern examples.
“Het interessantste was dat 75 % van die mensen in een heel moeilijk omgeving gingen.”
Parents who shield children from every hardship may be removing the adversity that builds capability, as shown by a camp where a counselor's report about bruises triggered a two-week investigation.
Doug argues that modern society builds guardrails so children cannot figure out life, so parents protect them from the very hardships that build drive. He describes a family whose kids were allowed to take risks and got cuts and bruises at a camp. A 15-year-old counselor reported possible child abuse, which launched a two-week investigation into the family's life.
“This launched a two week investigation into their life”
Doug splits life into two circles, the things you must do to meet obligations and the things that satisfy you, and suggests pursuing both rather than assuming passion alone will pay.
Doug says people are told to live their passion, but a 20-year-old asking how to support themselves needs a way to start. He draws two circles, one for what you have to do, such as paying rent, and one for what you know satisfies you. He says you can try both, and that if you are lucky they intersect and you get paid for what you love, though it is not guaranteed.
“Ik heb twee cirkels opgemaakt. Een is de dingen die je moet doen.”
Schools reward compliance and resume-building, so students who take risks and build things are not celebrated, which Doug calls a tragedy.
Doug recalls a billionaire classmate who said the others got great grades while he was a C-minus student and a risk-taker who built companies. He argues that kids in high-risk neighbourhoods who build drug empires may have an entrepreneurial drive without an outlet, and that schools should celebrate entrepreneurship, risk-taking and trying things.
“so we don't reward that and i think it's a tragedy”
A palliative nurse who heard many deathbed stories found the top regret was living the life others expected, and the second was not taking more risks.
Doug cites an Australian palliative nurse who he says had probably listened to around 3,000 stories of people at the end of their lives. The most common regret was living the life others expected rather than the one they wanted. The second was wishing they had taken more risks.
“Rather than live the life They should've lived they lived the life that others expected of them”
People cannot move on from their family narrative until they face the truth of the world that shaped them, and that doing so takes bravery.
Doug says many people hold a fanciful view of their family and buy into a narrative because they fear that talking about it is disloyal. He says the work requires bravery and that people perpetuate the lie until they face the truth. He frames it as something to do for oneself and for one's children, so the story does not repeat.
“until you can face the truth of the world that shaped you, you can't move on”