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SAAS NORTH NOW Blog

How To Cultivate Resilience As A Founder (From An Exited Founder Turned VC)

Neil Grunberg, Co-Founder & Managing Partner, Storytime Capital

SAAS NORTH NOW #60

Hello to Canada’s SaaS Community,

Resilience is an often-talked about term in the startup world, but definitions may vary. For Neil Grunberg, a 3x startup operator turned VC, resilience has a specific set of ingredients. Speaking with SAAS NORTH, Neil shared his recipe for getting through every kind of experience as a founder.

Key takeaways:

  • Problems like needing to hire happen across all startups, but the impact to each company is unique.
  • To get through the difficult times when it seems like there is no answer, founders need to cultivate resilience.
  • Resilience is a function of asking questions, managing relationships, and dusting off when things go bad.

Dave Tyldesley

Co-Founder/Producer, SAAS NORTH Conference Editor, SAAS NORTH NOW

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Every day in a startup can feel like a punch in the gut. That’s not a feature or a bug, but simply reality. Which means there’s no way around it—only through. And the way you get through is being as resilient as possible.

As a 3x-operator-turned-VC with his firm Storytime Capital, Neil Grunberg has experience with resilience, both in his own work and seeing how the best founders in his portfolio work through trying times. Speaking with SAAS NORTH, Neil shared the ingredients his experience says are most critical for building founder resilience.

All problems look the same when you’re stuck

While there are some similarities in growing companies—hiring, go-to-market, sales, and product evolution among them—Neil said every company faces those challenges in unique ways based on its history, founding team capabilities, and market conditions. “The fingerprint of each company is so different,” said Neil. “It’s not cookie cutter A to B to C.”

To illustrate this point, Neil shared examples of three different companies in the Storytime Capital portfolio that are facing what looks like the same issue: talent growth after raising capital.

Understanding mechanics: The first company is ready to hire some amazing people, but isn’t sure about the mechanics of hiring, compensation, titles, or employee options. With that in mind, the solution Neil and the team proposed was to bring on competent legal and HR counsel to talk through option pools (and other details), so the founder could make informed decisions.

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Building now for growth later: The second company has a firm grasp on what the organization needs to accomplish in a few years, but isn’t sure the kind of talent necessary today to make that happen. With this kind of challenge, the next step was to design an ideal org chart for the future state—identifying the types of people necessary to keep that success going—then working backwards to figure out what roles need to be hired now to either grow into or manage that ideal org chart in the future.

Individual contributor versus executive: The third company faced yet another different version of the talent challenge. Neil said the company had some great initial traction and wanted to hire a senior leader to manage it. But the issue was the company’s go-to-market plan was not 100% clear. As a result, said Neil, hiring a senior leader might not go well—instead, they needed to figure out what they needed rather than making a big hire too soon. The solution, for instance, would be more like hiring some specialist individual contributors or freelancers to run some tests on different approaches first. From there, the right senior leader could be brought on to scale whatever the experiment uncovered to be the path forward.

The ingredients of resilience

If you find your startup in one of the three scenarios above, then you have a good suggested path forward. But what about if you aren’t sure what your real problem is? Sure, you’ve got “growth challenges,” like any other startup, but what’s the nuance in your situation?

Finding that out, said Neil, requires resilience. And for Neil, resilience starts with asking questions.

“They all have different nuances based off of just the DNA of the company,” said Neil. “But in all cases, the founders are doing an incredible job at asking questions which then flushed out the problem they were actually facing.”

Simply asking questions randomly isn’t enough. The types of questions that lead to true founder resilience come from a few different factors.

Don’t stick your head in the sand: As a founder, you can’t pretend a problem doesn’t exist. However, this is also good news—if you have an urge to ignore something,”that’s probably the thing you need the most help with.”

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Manage relationships with communication: Whether customers or investors, people want to see how you engage with them before committing. This is something Neil has seen as an operator at AlayaCare and as a VC. For example, Neil met Kaylee Astle at SAAS NORTH and was intrigued by her startup Blanka, a private label makeup manufacturer. However, he was particularly wow’ed by Blanka’s regular (private) investor updates. He got Kaylee’s updates for six months before starting diligence on the company, but cited that communication as one of the key reasons he ultimately chose to invest in the company.

“The responsiveness and the way someone interacts with the venture fund is a direct indication to how they are as a leader, how they are as a manager, how they are as a customer advocate, etcetera,” said Neil. “I don’t know of a venture fund that would invest without having measured that aspect.”

Dust off when things go bad: Even with amazing self-awareness and intuition, things can go poorly. The key is to take what you can from the experience and learn from—but not let it stop you from continuing to act.

“It’s being able to say, okay, that was not what we wanted,” said Neil. This was not how this turned out. This deal failed. Whatever. Then saying, okay, let’s figure out how we bounce back from this versus going into a vicious death cycle because you’ve had a bad bounce.”

Every day brings a potential new challenge for a founder. Success might be attributable in part to luck, but in Neil’s experience, it’s more so to the intelligence to follow tailwinds, the resilience to bear headwinds, and the self-awareness and honesty to identify what kind of wind you’re facing.

“Those are the real things that are the marks of winners in my mind,” said Neil. “Even if we at Storytime Capital pass on an investment, I can tell you, nine times out of ten, if a founder has all of those characteristics—even if the market might not be perfect, even if the problem might not be perfect—they’re going to find their way.”

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Hello to Canada’s SaaS Community,

Resilience is an often-talked about term in the startup world, but definitions may vary. For Neil Grunberg, a 3x startup operator turned VC, resilience has a specific set of ingredients. Speaking with SAAS NORTH, Neil shared his recipe for getting through every kind of experience as a founder.

Key takeaways:

  • Problems like needing to hire happen across all startups, but the impact to each company is unique.
  • To get through the difficult times when it seems like there is no answer, founders need to cultivate resilience.
  • Resilience is a function of asking questions, managing relationships, and dusting off when things go bad.

Every day in a startup can feel like a punch in the gut. That’s not a feature or a bug, but simply reality. Which means there’s no way around it—only through. And the way you get through is being as resilient as possible.

As a 3x-operator-turned-VC with his firm Storytime Capital, Neil Grunberg has experience with resilience, both in his own work and seeing how the best founders in his portfolio work through trying times. Speaking with SAAS NORTH, Neil shared the ingredients his experience says are most critical for building founder resilience.

All problems look the same when you’re stuck

While there are some similarities in growing companies—hiring, go-to-market, sales, and product evolution among them—Neil said every company faces those challenges in unique ways based on its history, founding team capabilities, and market conditions. “The fingerprint of each company is so different,” said Neil. “It's not cookie cutter A to B to C.”

To illustrate this point, Neil shared examples of three different companies in the Storytime Capital portfolio that are facing what looks like the same issue: talent growth after raising capital.

Understanding mechanics: The first company is ready to hire some amazing people, but isn’t sure about the mechanics of hiring, compensation, titles, or employee options. With that in mind, the solution Neil and the team proposed was to bring on competent legal and HR counsel to talk through option pools (and other details), so the founder could make informed decisions.

Building now for growth later: The second company has a firm grasp on what the organization needs to accomplish in a few years, but isn’t sure the kind of talent necessary today to make that happen. With this kind of challenge, the next step was to design an ideal org chart for the future state—identifying the types of people necessary to keep that success going—then working backwards to figure out what roles need to be hired now to either grow into or manage that ideal org chart in the future.

Individual contributor versus executive: The third company faced yet another different version of the talent challenge. Neil said the company had some great initial traction and wanted to hire a senior leader to manage it. But the issue was the company’s go-to-market plan was not 100% clear. As a result, said Neil, hiring a senior leader might not go well—instead, they needed to figure out what they needed rather than making a big hire too soon. The solution, for instance, would be more like hiring some specialist individual contributors or freelancers to run some tests on different approaches first. From there, the right senior leader could be brought on to scale whatever the experiment uncovered to be the path forward.

The ingredients of resilience

If you find your startup in one of the three scenarios above, then you have a good suggested path forward. But what about if you aren’t sure what your real problem is? Sure, you’ve got “growth challenges,” like any other startup, but what’s the nuance in your situation?

Finding that out, said Neil, requires resilience. And for Neil, resilience starts with asking questions.

“They all have different nuances based off of just the DNA of the company,” said Neil. “But in all cases, the founders are doing an incredible job at asking questions which then flushed out the problem they were actually facing.”

Simply asking questions randomly isn’t enough. The types of questions that lead to true founder resilience come from a few different factors.

Don’t stick your head in the sand: As a founder, you can’t pretend a problem doesn’t exist. However, this is also good news—if you have an urge to ignore something,”that’s probably the thing you need the most help with.”

Manage relationships with communication: Whether customers or investors, people want to see how you engage with them before committing. This is something Neil has seen as an operator at AlayaCare and as a VC. For example, Neil met Kaylee Astle at SAAS NORTH and was intrigued by her startup Blanka, a private label makeup manufacturer. However, he was particularly wow’ed by Blanka’s regular (private) investor updates. He got Kaylee’s updates for six months before starting diligence on the company, but cited that communication as one of the key reasons he ultimately chose to invest in the company.

“The responsiveness and the way someone interacts with the venture fund is a direct indication to how they are as a leader, how they are as a manager, how they are as a customer advocate, etcetera,” said Neil. “I don't know of a venture fund that would invest without having measured that aspect.”

Dust off when things go bad: Even with amazing self-awareness and intuition, things can go poorly. The key is to take what you can from the experience and learn from—but not let it stop you from continuing to act.

“It’s being able to say, okay, that was not what we wanted,” said Neil. This was not how this turned out. This deal failed. Whatever. Then saying, okay, let's figure out how we bounce back from this versus going into a vicious death cycle because you've had a bad bounce.”

Every day brings a potential new challenge for a founder. Success might be attributable in part to luck, but in Neil’s experience, it’s more so to the intelligence to follow tailwinds, the resilience to bear headwinds, and the self-awareness and honesty to identify what kind of wind you’re facing.

“Those are the real things that are the marks of winners in my mind,” said Neil. “Even if we at Storytime Capital pass on an investment, I can tell you, nine times out of ten, if a founder has all of those characteristics—even if the market might not be perfect, even if the problem might not be perfect—they're going to find their way.”