What Would It Take?

by | May 26, 2022

Brett Hagler serves as CEO and Co-Founder of New Story, an organization pioneering solutions to end global homelessness. He’s passionate about speaking on leadership, creating a team culture of innovation, helping other social entrepreneurs, and partnering with companies to give their team members the opportunity to make a direct life-changing impact. He is a friend of Workmatters, and we are so grateful and excited to have him speak on the main stage at our 2022 Workmatters Conference in September.

Bold ideas attract bold people.

It’s a mantra I’ve lived by throughout my entrepreneurial career and one that has helped my team and I grow New Story from one home built to thousands

It’s proved to be true time and time again: The bolder the idea, the bolder resources you’ll attract. One of the most prominent examples of this is SpaceX and Tesla. These projects have attracted some of the boldest people in the world to bring them to life because the vision of these projects is just that: bold.

This mantra can be applied to any endeavor. If you have a bold idea for a startup, you will attract bold investors. If you’re bold in your growth strategies for your nonprofit, you will attract bold donors and bold team members. If you have bold standards for your new service-based business, you will attract customers who are tired of the status quo.

So how do you come up with bold ideas that will attract bold people? At New Story, our strategy is to think big, break it down, and then execute.

Think Big

One of the best ways to think big is to pose the question: “What would it take to______?”

In the past, we’ve filled in the blank with ideas like, “house 1M people, go from $10M/yr to $100M/yr in five years, recruit extraordinary talent, and decrease the cost of housing by 30%.”

The level of boldness will vary from individual to individual and company to company, but you can always make the choice to go bolder—and I love how posing the question, “what would it take to…,” pushes you to do that.

Break it Down

At New Story, once we have a bold idea we want to chase, we then break down the idea into smaller, achievable goals so that we have something tangible to start working on. This is huge because more likely than not, when you’re chasing a bold idea, you’re going to come up against some massive challenges.

But when you break down a bold idea into achievable goals or steps, you see that it’s possible… you see what it would take, and you’re prepared to face challenges when they arise.

And all of those things set you up to execute with passion and persistence.


When it comes to executing on your bold ideas, it’s important to approach each step of the journey with three things:

  • Humility: Boldness must be balanced with humility. This may sound contradictory, but that’s how leadership goes. Inspirational, bold leaders set a vision and then obsessively learn from a humble posture and shamelessly seek help.
  • Sincerity: Boldness must be genuine. This isn’t a hack. You have to truly believe it’s possible, otherwise you’ll have a hard time convincing anyone else that it’s possible.
  • Follow-through: Boldness requires you to keep your promises. Talk is cheap. If there’s no follow-through on what you said you were going to do, you’ll lose support and momentum—fast. Make sure you’re ready to give it your all to make the vision happen.

Someone who’s helped countless entrepreneurs execute on their big ideas (including me and my team of Co-founders) is Paul Graham, Co-founder of Y Combinator. In one his blog posts, he wrote:

“And fortunately ambition seems to be quite malleable; there’s a lot you can do to increase it. Most people don’t know how ambitious to be, especially when they’re young…They don’t know what’s hard, or what they’re capable of. And this problem is exacerbated by having few peers. Ambitious people are rare, so if everyone is mixed together randomly, as they tend to be early in people’s lives, then the ambitious ones won’t have many ambitious peers. When you take people like this and put them together with other ambitious people, they bloom like dying plants given water. Probably most ambitious people are starved for the sort of encouragement they’d get from ambitious peers, whatever their age.” 

So, how can you apply the “what would it take to” question to your own team?

You might ask: What would it take to double our revenue in 2022? Increase our talent density? Land the dream partner?

You can even use this question to think big about your career trajectory. What would it take to go from where you are today to a bolder vision of where you want to be in three years?

Thinking big like this will force you to make changes and set a new standard for yourself and your business. You’ll differentiate yourself (and/or your company) and that alone will attract bold people to your mission. Because like Paul Graham said, boldness is rare.

Photo of Brett Hagler

Brett Hagler

Brett serves as the CEO and Co-Founder of New Story, an organization pioneering solutions to end global homelessness. Brett is a Y Combinator graduate, cancer survivor, recognized on Forbes’ 30 Under 30 list, and New Story was named among Fast Company’s “Most Innovative Companies in the World” four times in the last five years.