What’s actually slowing this PC down?
Pick the symptom - the matching free tool is one click away.
Rich Barton’s “swing for the fences” philosophy is a case for pursuing ambitious goals when the possible payoff is unusually large—not a claim that every risky bet is wise. In a 2011 interview, the Zillow co-founder argued that big goals can inspire people to do more, provided an organization allows room to miss, learn and try again. His later comments and Zillow’s retreat from its iBuying venture add an important qualification: the risk he endorsed was tempered, and a bold bet can carry real costs.
What did Rich Barton mean by “swing for the fences”?
At a GeekWire event in Seattle in October 2011, Barton answered a question about startup ambition with a baseball analogy. He argued that taking a shot at an exceptional outcome need not require more effort than settling for a smaller one:
“Look, you have an at bat, and it takes just as much energy to swing for the fences as it does to bunt. OK. So, why bunt? Why bunt? Why not swing for the fences? I would argue that it is just as likely that you will succeed if you swing for the fences as if you bunt, and the outcome will be much more magical.”
The line expresses Barton’s argument, not a proven rule about the odds of ambitious versus conservative plans. The interview does not establish that high-risk strategies are generally just as likely to succeed as low-risk ones. The point is about the appeal of aiming high when the potential outcome could be transformative.
Free tools Windows power users keep installed
One-click scans. No signup required.
#1 Best Overall
Why does the philosophy depend on workplace culture?
Barton’s idea is not only about an individual’s appetite for risk. He also praised organizations that encourage people to pursue ambitious ideas and do not automatically punish them for a miss. Describing Microsoft’s culture, he said:
“The great thing about Microsoft then, and now, is that it encouraged dreamers and people like me and people like us to take big swings. And, if you missed, not actually fire you and punish you for it.”
That distinction matters: if one failed attempt ends someone’s career, people have a strong reason to avoid uncertain projects, even when the potential upside is substantial. Barton’s view is that high expectations can draw out strong performance, while tolerance for a miss gives people space to attempt ambitious work. It is an argument for informed experimentation, not for ignoring consequences or protecting every unsuccessful idea indefinitely.
What role do failure and persistence play?
Barton has connected risk-taking with learning from setbacks. A 2016 GeekWire report on his writing described his view that taking risks teaches people to work around obstacles and that failure can inform a stronger next effort.
Rank #3
- we like to ship out right away
In a 2020 Zillow-published conversation with Netflix co-CEO Ted Sarandos, Barton put the emphasis on learning and continuing:
“I would say that to all the great small business people out there, it’s okay to fail. Dreamers and innovators absolutely fail. The key is to learn from the failures and to have the tenacity and courage to continue to move forward.”
Failure, in this account, is useful only if it produces learning and better decisions. Persistence does not mean repeating a failing plan unchanged; it means carrying lessons forward while continuing to work toward worthwhile goals.
What does “tempered” risk-taking mean?
In a company account of a 2020 CNN Business interview, Barton described himself as “very comfortable with risk that is tempered,” which he associated with courage. That qualification helps distinguish his philosophy from simply choosing the most uncertain option. A big swing still needs judgment: leaders must consider the possible upside, how much uncertainty they are accepting, whether they can absorb a miss and what evidence would prompt them to change course.
Recommended Free Tools
Best Value
- If you want to build a better future, you must believe in secrets.
- The great secret of our time is that there are still uncharted frontiers to explore and new inventions to create. In Zero to One, legendary entrepreneur and investor Peter Thiel shows how we can find singular ways to create those new things.
What does Zillow’s iBuying retreat show—and not show?
A November 2021 GeekWire retrospective linked Barton’s language about big swings to Zillow’s iBuying venture, which involved buying and reselling homes. Zillow announced that it would wind down Zillow Offers. The episode shows that an ambitious bet can fail and have material consequences, including criticism of the strategy and effects on employees and investors. It also underscores the importance of accountability and responding when a bet is not working.
The retrospective is a 2021 account, not a current report on Zillow’s business or finances. It does not establish that every bold strategy is destined to fail—or that Barton’s philosophy guarantees success. The company’s earlier entrepreneurial record and its acquisition of Trulia provide context for its willingness to make major bets, but they do not prove that a “big swing” approach works in every organization.
How to apply the idea without treating risk as a virtue
For a leader, founder or employee weighing an ambitious project, Barton’s argument is most useful as a prompt for disciplined questions—not as a blanket instruction to take bigger risks:
- What is the potential outcome? Be specific about what makes the goal worth pursuing rather than assuming that ambition alone makes a project valuable.
- What is uncertain? Identify the assumptions the plan depends on; do not treat an untested probability claim as fact.
- Can the organization absorb a miss? Consider the people, resources and other commitments that could be affected if the attempt fails.
- Will people be able to learn? A culture tolerant of failure should still expect honest evaluation and useful lessons.
- What would trigger a change in course? Agree on how leaders will respond if evidence shows that the plan is not working.
Barton’s baseball metaphor is a memorable defense of ambition, but its useful lesson is conditional: aim high when the potential outcome warrants it, make room for informed attempts, learn from misses and remain accountable for what those attempts cost.
The Tool Desk
Outbyte Driver Updater FREEFix the driver behind crashes, sound loss and screen glitchesFind Drivers →Outbyte PC Repair FREERepair Windows errors before they cause bigger problemsFix Now →Quick Recap
Product prices and availability are accurate as of the date/time indicated and are subject to change. Any price and availability information displayed on Amazon at the time of purchase will apply.
