Four years ago, Ryan Breslow was on the cover of Forbes magazine after his $11 billion (€9.6 billion) fintech start-up, Bolt Financial, made him one of the world’s youngest billionaires.
Bolt’s value has since crashed and the 30-something Breslow is now shedding staff with a vigour that is bracing even for Silicon Valley.
“We had an HR team, and that HR team was creating problems that didn’t exist, and those problems disappeared when I let them go,” he told a recent Fortune conference in Atlanta.
Also, he said, his smaller, more junior workforce was doing a much better job than the “big credentialled pedigreed professionals” he was saddled with before.
No matter what you think of HR and overpaid loafers, I think we can agree Breslow is the sort of boss best avoided.
Alas, it is impossible to dodge people who make working life miserable.
My attention was drawn to one of the most egregious specimens this week after Harvard Business Review published an analysis of the perils facing the kiss-up-kick-down colleague.
That phrase did not actually appear in the article, which was technically about the widely proffered advice to aspiring leaders to “network up” and use helpful senior “sponsors” to oil one’s ascent.
But its message still applies: overemphasising relationships at the top can endear you to top bosses but annoy everyone else so much that it limits long-term progress. This is true.
Being nice to everyone is far smarter than a lot of ambitious wannabes ever realise.
Abject crawling can even irk some bosses, or at least bemuse them. As a distinguished contact of mine used to tell me about one of his more fawning offsiders: “I’m not sure how good he is, but he never stops telling me how amazing I am.”
Even so, I am afraid one of the most infuriating aspects of the toadying sycophant is they keep succeeding.
Time and again, I hear friends and relatives in all types of industries despairing of moderately talented bootlickers who rise remorselessly through the ranks while bullying juniors with abandon.
A variant of the species is the middle manager who kisses up and down, but kicks out sideways at peers they deem a threat. I have seen these people in action, and being around them is no fun.
The maddening thing about this behaviour is it is obvious to anyone working closely with these people, yet invisible to everyone else.
Too rare are the public outings of the kind that design guru Stephen Bayley delivered this year when he wrote of his time working with Peter Mandelson on London’s Millennium Dome project.
He was “inclined to kiss up and kick down”, Bayley said of the disgraced peer. “Serpentine too.”
[ Why job interviews are increasingly becoming AI testsOpens in new window ]
Good employers know how debilitating the kiss-up-kick-down manager can be. It’s one reason for the dreaded 360-degree performance review, an often time-consuming drain that can be gamed by office politics pros.
But these assessments can still help. Likewise, approachable bosses who spend time roaming the floor and chatting with staff are apt to find out more about their managers than those who lock themselves away in remote offices.
No solution is foolproof. I am told one of the few upsides of working with a dedicated kiss-up kick-downer, who horrifically becomes one’s boss, is that it inspires a level of bonding more profound than a dozen team-building away days.
Ultimately though, I fear the problem will always be with us.
That’s why it pays to think of all those who are celebrated for being precisely the reverse, such as Walter Jones, the North Carolina Republican congressman who died in 2019.
He was, one Washington observer wrote, the “polar opposite” of the many DC residents whose formula for advancement was to flatter the powerful and kick down at the powerless.
Jack Bogle, founder of the Vanguard asset management giant, died the same year as Jones. “While some leaders kick down and kiss up, Jack did just the opposite,” wrote one of his earliest employees. “He expressed deep interest and concern about his people. He was always joking. He had a bunch of kids, and when he came downtown to work, we were his kids.”
That’s a good way to be remembered and a helpful thing for an office kiss-up never to forget.
- Copyright The Financial Times Limited 2026
