Inside the 500 Accelerator is a weekly series by 500 founder Troy Sultan. Now, 13 weeks in, Troy gets real and shares the hardest question that he — and many other founders — have had to face. 

“Dude, how’s it going?”

It’s quite literally the hardest question you can ask me.

A few years ago I wouldn’t have minded as much. I had a canned answer I got good at reciting. It told a story of things going great, because that was the path of least resistance. I’d keep it surface-level, short and always positive. Because no one asks questions when things are going good. And honestly, who the hell wants to hear about my problems?

I’ve been practicing vulnerability for the past year, challenging myself to step outside the closed, unemotional shell I’ve lived in for so long (my whole life, to be exact).

It’s working. I’ve grown more vulnerable at a material rate. I’m opening up with ease and connecting more deeply with friends and colleagues who’ve begun to understand what’s behind the confident persona I’ve spent a lifetime building up.

“Are you a super-human?”

No, but I’ve spent so much time wanting people to believe I was.

Last week I performed a solo on stage, for 15 minutes, in front of a sold out crowd of 80 people — one of the most vulnerable moments of my entire life. It was the result of months of challenging myself to dig up my deepest struggles, embarrassing tendencies, and memories I’ve chosen to keep buried for so damn long.

Ultimately, I was admitting to the world my single biggest insecurity:

I’m not perfect.

As a leader, it seems necessary to build a moat around your emotions, not letting anyone break beyond the surface to see what you’re really thinking or worrying about, because admitting that your shit isn’t entirely together is the moment everyone loses faith in you, right?

I believed this for so long. Yet, I couldn’t have been more wrong.

People are, well, people. And they understand you’re one of those too. While you need to both understand and believe in the future you‘re creating, you don’t always need to have the answers.

Being vulnerable enough to admit you’re not sure, and that you don’t have things entirely figured out but you’re doing everything you can— is a much more relatable stance, and one that levels you with those around you, allowing them empathize with your reality and connect with you on a much deeper level than before.

You become a human.

During these last few weeks, I’ve noticed my vulnerability showing up when someone queried with anything resembling “the question.”

Now, my answer varies depending on how I’m actually feeling that day or week. It’s a genuine summary of what’s on my mind at that moment. The sentiment may skew positive or negative, but it’s real. And the real answers aren’t always what you expect to hear.

Today I wonder whether my newfound vulnerability comes at the expense of confidence. These days, I’m waking up to a more real me — not just to those around me, but to myself. An honest, authentic me that’s missing it’s sense of irrational optimism and positivity (and maybe even naiveté). A me that’s facing the reality of the insanely high bar I’ve set for myself.

Part of me questions the self-fulfilling prophecy of telling everyone things are great. If I say it enough, will I start to believe it?

The challenging part for me is that things really are going great if I limit the context to what we’ve accomplished so far. I’m incredibly proud of myself and our team for where we are today vs. say, 6 months ago. But once my ambitions creep back into the frame and I consider what we’re after long-term, I question whether we’re moving fast enough; whether we’re building the right team, culture; whether we’re doing enough, period.

For now though, I’m enjoying it. I’m learning how I want to think. I know myself much better from the honesty. Just be warned — I might take you down a road less traveled if you happen to ask me how things are going. 😉

Oh, and some other stuff happened in the last 3 weeks as well:

  • Storytelling for Innovation w/ David Riemer
  • Batch 15 Demo Day Movie Night (this was fun)
  • Pitch prep w/ Andrea (check her out in Forbes!)
  • Fireside chat w/ Steli Efti, CEO of Close.io
  • VC Mingle
  • Late night pitch prep w/ Marvin
  • Fireside chat w/ Jason Van den Brand, CEO of Lenda
  • Fireside chat w/ Jessica Mah, CEO of InDinero
  • Pitch prep w/ Andrea
  • Late night pitch prep w/ Marvin (can you tell we care about pitching?)
  • Fireside chat w/ Ken Lin, CEO of CreditKarma
  • 10 Steps to Mastering the Art of Building a Consumer Unicorn w/ Jim Scheinman of Maven Ventures
  • Late night pitch prep w/ Marvin
  • Scaling From 0 to 300 Demos a Month w/ Greg Pietruszynski, CEO ofGrowbots
  • Fireside chat w/ Pivotal labs: Drunk User Testing
  • MOAR pitch prep w/ Andrea
  • Fireside chat w/ Hiten Shah, CEO of QuickSprout