Company stories

Why we're building twenty

twenty team

Four beliefs behind twenty’s design that we hope resonate with you—whether you’re just starting your twenties, wrestling with a quarter-life crisis, or looking back on this “defining decade.”

You can take a million different paths in your twenties.

  • Will you launch a startup or climb the corporate ladder?
  • Get married and have kids, or swear off dating apps till your thirties? 
  • Move to Mexico City? Go to grad school?
  • Become a doctor, a venture capitalist, a TikTok content creator or all the above?!

Back in college, you had a clear blueprint for success, but now, you’re on your own. You graduated from the “best four years of your life” and then entered a dark abyss. How do you carve a path that’s authentic to you and true to your instincts, values, and ambitions? How do you make the most of this “defining decade” and live without regret? There’s no right or wrong answer, so the best way to find clarity and conviction is through speaking with people who were just in your shoes.

That’s why we’re building twenty. Think of twenty as your trusted sounding board for navigating career and life crossroads. For figuring out what you really want and carving your own path, alongside a community that’s figuring it out, too.

Here are four beliefs behind twenty’s design that we hope resonate with you—whether you’re just starting your twenties, wrestling with a quarter-life crisis, or looking back on this “defining decade.”

College is failing to prepare us for the real world

At first, you might think of classic adulting 101 skills, like changing a tire or filing your taxes. But we believe the biggest gap between college and the real world is actually around mindset.

College teaches us that if we want to get straight As, we need to follow the rules, memorize facts, and give teachers the "right answer." However, these behaviors rarely help us in the real world, an ambiguous space that revolves around trust, relationships, communication, resilience and thinking on our feet.

When we graduate from college, we have to unlearn many student behaviors and shift to a new mindset and approach. We have to evolve from:

  • From giving the right answer 👉 to asking the right questions
  • From grades and report cards 👉 to defining our own metrics for success. 
  • From following academic calendars 👉 to deciding how to best spend our time and money.
  • From college dorms 👉 to deciding how and where to live on a budget.
  • From college majors 👉 to forging meaningful career paths.

If you’re still making this transition at 28 years old, you’re not alone. On that note...

Nobody has it all figured out

All of us are wrestling with something - personally, professionally, socially - that many others have been through before and can help us navigate. Nobody has all the answers in their twenties (or in any decade, for that matter!).

At twenty, we see the challenges faced by twenty-somethings falling into three broad categories:

  • Skills, like product management
  • Personal experiences, like being a queer woman in finance. 
  • Milestones, like buying your first home or getting into grad school. 

The tricky part is that the resources required to navigate each of these categories are scattered in a thousand different places. There’s no right or wrong answer as to how to navigate your twenties, but the best way to find clarity and conviction is through speaking with people who were just in your shoes. However, finding such a person is not easy.

twenty is the only platform to bring all of these categories into one place, with a special focus on providing access to 20-somethings to people who were just in your shoes.

Nothing compares to human interactions

At our core, we believe that live experiences, 1:1 conversations and human relationships have the greatest potential to transform our lives and careers. Sure, ChatGPT can aggregate helpful information in one place and show us which doors to knock on, but people actually open those doors, make hiring decisions, and turn personal insights into action.

While meeting people decades older (or younger) is always inspiring, the most actionable feedback comes from people who have just tackled the skill, experience or milestone that's next for you. That’s exactly who our twenty mentors are. Ambitious and successful operators, founders and investors who’ve been there, done that.

People are inherently altruistic

Finally, behind every human is a wide circle of support—mentors, friends, family members, teachers, managers, coaches, and teammates—who helped us get to where we are today. It's a natural human instinct to pass our learnings onto others. It's rewarding, meaningful and confidence-generating. We see this quality every single day in our mentors. Many of them say that their twenty mentorship sessions are the best part of their day.

This generosity of spirit extends beyond individual mentor-member relationships—it’s part of the entire twenty community. It’s showcased within the hundreds of people in our Slack community, our monthly events, the dozens of anonymous questions asked and answered on our portal, and more. Joining a community with altruism at its core can have a ripple effect on the rest of your professional and personal life, too.

Want to join twenty? Apply here and hear back within 3-5 days. We can’t wait to meet you!

Wanna dig deeper?

Join twenty today to connect with mentors who’re sharing their firsthand experience on this topic (and more)
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