Inside the 500 Accelerator is a weekly series by 500 founder Troy Sultan. Today, 10 weeks in, Troy presents “inspiring” takeaways from other Batch 16 founders. But it’s not all fluffy kittens and cotton candy… being a founder is tough, even with world-class support and mentorship. This week, the founders get real.  

Accelerators are like kitchens, not restaurants. They give you access to all the tools, ingredients and guidance needed to satisfy your hunger — but it’s up to you to mix things up, try new approaches and make use of what’s available. This is contrary to a restaurant where you show up, sit down and expect to have your hunger satisfied.

My team and I recently reflected on the first 10 weeks of 500, asking whether we’re happy with what we’ve gotten from the program so far. Should we make any changes to during the final 6-week stretch? Would we benefit from doing more or less of anything? A recalibration of sorts.

That made us wonder how other teams felt about their experience. Were they getting similar value? Were they struggling in the same ways? Were they being robbed of sleep by the same nightmares and finding motivation in the same dreams?

Accelerators don’t do the work for you — you get out of the experience what you put in, and because of that, every team has a slightly (or largely) different experience.

I sat down with five fellow B16 founding teams to understand how they’re feeling just 6 weeks from Demo Day. Read on to hear what they had to say.


Johnny Warstrom of Mentimeter 

They dig deep into our company but then again they don’t. They don’t care what we do as a product or service. They care about the peripheral: metrics, go-to-market, distribution channels, and they challenge us to try different things rather than getting into the weeds.

On moving a team of 7 from Sweden:

Coming here was a huge risk for us. There were many unknowns and the value we’d get was unclear. What we knew they’d take X%, it’s Y weeks long, and then there’s demo day. But the learning, speakers, mentor office hours, relationships and office banter have completely changed our perspective. We’ve grown a lot.

As for moving our whole team here vs. the just the founders, that was never a question. We‘re only 7 people. At this stage everyone needs a founder mentality. That’s how you create a self-managing company without having to steer in the details. The entire program is geared toward founders, their challenges, and headaches of building a company. We’re all getting that here. The whole team is getting advice as founders and that has tons of long-term value.

On advisors and 500 POCs:

They dig deep into our company but then again they don’t. They don’t care what we do as a product or service. They care about the peripheral: metrics, go-to-market, distribution channels, and they challenge us to try different things rather than getting into the weeds. I was afraid of strong opinions about how to run our business. I hate that kind of advice. They take a very mature and challenging approach to helping companies, which I love.

On expectations and fundraising:

We have 4 angels currently. They’d be happy with 3–5x return on their investment. If we raise more money, expectations skyrocket and we’ll need to deliver much more. We need to decide whether we want to go all in now, or build organically and maintain full say in our outcome. Most companies here are looking to fundraise, but there are also ones challenging that. The goal is to build a great company, which can come in different shapes and sizes. There are many routes to getting there.

Coming from Sweden, you get the impression that founders in the Valley are mindlessly going after investment. I’ve been pleasantly surprised that people seem to be thinking about it in a thoughtful way.

On personal challenges:

My biggest challenge for last year and a half has been knowing when to be firm in knowing what I know and pushing that through vs. when I should be open to have my view point challenged. And that goes for all stakeholders: cofounders, employees, investors, 500 advisors, etc. There’s a fine line between being confident and knowing your shit and being someone who doesn’t know where we’re heading or how we’ll be successful. That’s something I struggle with every day and it’s gets bigger as the company grows and our vision becomes more ambitious.


Justin Howell and Kirk Voltz of Rize

If there’s one thing I worry about for the long run, it’s whether we’re moving too slowly. Speed is probably the biggest thing that keeps me up at night.

On moving fast and avoiding perfection:

We’ve learned to deeply understand things can’t and shouldn’t be perfect. Perfect is the bane of learning.

What moving fast means is getting out there, getting comfortable with the fact that things will suck for a period of time. But that’s how you’ll learn fastest. We’re very good at being thoughtful which is one of our strengths and weaknesses. It makes it easy to move slower than we should.

It’s challenging as a FinTech company where moving fast and breaking things could be a complete company killer. We need to get comfortable living in the grey area. We can’t do everything perfect — we’re not a big company. If we don’t find that line and bump into it, we’re moving too slow.

On managing change:

The set of problems you face at each stage of the company is completely different. They’re equally hard, but different. It never gets easier. It’s one thing to understand this at an intellectual level but another thing entirely to go through it. Everything you thought you knew and you thought you were good at — you don’t, and you’re not.

Your job completely changes every few months. Where you’re spending time now will be miles away from where you’re spending your time in 6 months.

On managing psychology:

There’s more costs to FinTech from a regulatory and security perspective — just more costs to running the business and more time involved, yet you’re held to the same standards as everyone else.

These don’t necessarily keep me up at night but they’re top of mind. I know we’ll keep cranking no matter what and get it done. It’s a question of how long it takes and how hard it is to get to that point.

It’s hard to to avoid thinking about what might make our lives more difficult —  like the fundraising environment. That definitely won’t help things.

If there’s one thing I worry about for the long run, it’s whether we’re moving too slowly. Speed is probably the biggest thing that keeps me up at night. We’ve been at it for a year straight as we approach our beta release next month, and all the work we’ve done thus far was just to get to the starting point.

It’s about stamina. It’s a mental game more than anything else. I’m generally pretty good here, but sometimes I stop and say “Damn, I’m beat.” Then I have to find a way to recharge and get back to it. Sometimes you see a wall coming at you when you’re already tired and you just have to power through it.


Collin Gutman of WorkAmerica

Coming in, we knew there were more ways to tap into our customers — but we didn’t know exactly how, what or why. Now we know which marketing channels work and what to avoid, and how that affects our resource allocation, our growth, pitch, etc. We went from acquiring users 1 way to 4 ways — that’s a mindset shift for the team.

On decision making and leveraging the 500 partners:

Colin Gutman WorkAmerica CEOWe’re making big decisions to try new things which is uncomfortable, but concretely talking through the approach with people who have battle scars and experience that helps us validate. We have our own theories within our team but no way of knowing who’s right. And if no one’s objectively right, we need to know where to start and how to make these decisions. 500 has been hugely valuable as an arbitrator for us.

Coming in, we knew there were more ways to tap into our customers — but we didn’t know exactly how, what or why. Now we know which marketing channels work and what to avoid, and how that affects our resource allocation, our growth, pitch, etc. We went from acquiring users 1 way to 4 ways — that’s a mindset shift for the team. Now we have a pipeline of experiments and a process to run.

That said, I have to be my own sounding board. If you as CEO aren’t 100% committed to the direction you’re heading, the people you work with won’t be either. I spend time at night alone to hash this out so when I come into the office in the morning I’m concrete on the direction.

On what’s keeping him up at night:

What I’m worried about varies widely and changes quickly. We went from a local to national marketplace since joining 500. Before I was worried about going from 2 to 200 schools market by market, and now I’m worried about how to get all 200 at once.

I’m worried about growing revenue MoM. We’ve raised $2M to date, but I still question whether we’re a VC-backable business.

On fundraising:

Fundraising is funny because your ability to get it done may have nothing to do with the business itself. We’ve raised without substantial revenue traction, for example. A million other things go into it.

I’d guess most companies’ #2 goal coming into 500 was growth. I think the #1 goal was to raise money. The perception is that coming to 500 is a very effective way to raise a seed sound. I’m really curious to see how that plays out. How have goals changed? How much does 500 actually increase fundability?


Frank DeGeorge, Nick DeGeorge and Scott Hansbury of YouStake 

The blunt honestly of everyone here is also refreshing. Neither party has time for bullshit, and we love how apparent that is.

On managing time and picking spots:

We knew the time would go fast. At first we took a sponge approach and tried to attend everything but there’s just not enough time for all of us to do that. We had to define roles and ownership areas and develop a cadence.

The program calendar starts to lighten up as time goes by, which works well. We went crazy at the beginning. There was so much info to digest. We figured if we documented it well we can use it later. But we’ve had to pick our spots.

On mentors and POC advice:

It’s surprising how how much they care but yet how little they’re interested in managing the details of your company. Everyone’s accessible but you need to know what you’re looking for and proactively find out who can help you.

It’s really easy for a company to come here and put their head down and not take advantage of everything they have access to. The blunt honestly of everyone here is also refreshing. Neither party has time for bullshit, and we love how apparent that is.

On challenges, pressure and what’s keeping him up at night: 

I’m always thinking about where I’ve failed in the past and making sure don’t repeat those mistakes. How do I keep us on the right path as a business?

There’s definitely a lot of pressure on the fundraise. We didn’t raise a lot of money before this, so in order to grow and utilize what we’ve learned here we have to raise money. But I’m more confident now than ever. I didn’t know our metrics before. If someone asked me CAC or how we’ll get new customers, I could talk to it at a high level but I couldn’t quantify it. Now I can talk to growth, churn, business model, vision, etc. with complete clarity. We’ve been forced to hash that out.


Charlie Mulligan and Samantha August of BrewPublik

Experimentation, smoke testing, and everything else we’ve learned — we’ve never done before. We’ve completely rethought how we’re approaching things. We regularly walk out of a partner meeting and think, “why the hell haven’t we been doing this?”

On challenges of having an east coast operation:

We’ve changed our approach as a company in many ways. We moved from NC to be here and have since opened our west coast market.

We knew it would be hard to manage our east coast operation from here, but it’s been harder than we imagined. It takes a toll on us, emotionally and physically. The day starts at 5am in Charlotte, NC where our other office is. My alarm goes off at 4am every day because it’s too shitty of a feeling to know I’m not in a position to support my employees if I’m asleep.

The camaraderie with people here helps a lot. We’ve built amazing friendships with people going through similar challenges. To know we’re not the only ones helps. We exert a lot of pressure on ourselves to succeed but when we’re struggling to meet growth #’s one week or traction is hit or miss, we don’t feel like our advisors are judging. They just want to help. That’s huge for us.

On progress: 

We pivoted our model 6 weeks in which the partners helped us validate. It’s been much easier to make decision with a sounding board of people who’ve done this before. That’s made a big difference.

Experimentation, smoke testing, and everything else we’ve learned — we’ve never done before. We’ve completely rethought how we’re approaching things. We regularly walk out of a partner meeting and think, “why the hell haven’t we been doing this?”


It was therapeutic to talk 1:1 with fellow founders facing similar challenges and psychological battles.

Overall, everyone had a positive outlook (as every founder should) about their momentum, prospects going into Demo Day, and the progress they’ve made over the last two months. Of course we have our complaints, but who doesn’t? It’s hard not to feel lucky waking up each day and getting to work on what you love. So here’s to all founders keeping that it’s as much about the journey as it is about the destination.

Content and happenings in the last 3 weeks:

  • You’ve Raised Money…Here’s how not to run out of it w/ Mike Sigal
  • Fireside Chat w/ Tiago Paiva, Founder/CEO of TalkDesk
  • Pitch Prep w/ Andrea Barrica
  • Poker night w/ YouStake
  • Mid-batch check-in and AMA w/ Marvin Liao
  • Fireside Chat w/ Jase Wilson, Founder/CEO of Neighborly
  • Startup survival guide on negotiation w/ Jay Mandal
  • More pitch prep w/ Andrea
  • PR Strategy and Data Storytelling w/ Chikodi Chima of Moonshot PR
  • Financial modeling workshop with Doug Scott of Ethic
  • Fireside chat w/ Gary Swart, Ex-CEO of oDesk / GP at Polaris Partners
  • Even more pitch prep w/ Andrea!

Thanks for reading! If you enjoyed, I’d love if you recommended below. You can continue to follow our journey on Medium or Twitter. And if your company can use more recruiting firepower, try spinning up a sourcing team with just a few clicks.

PS — Huge thanks to everyone who contributed their time and opened up about their experience to make this post possible.

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