Ask Why It Won’t Work, And Other Lessons This Founder Relies on While Building From 0 to 1
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Ask Why It Won’t Work, And Other Lessons This Founder Relies on While Building From 0 to 1

From all the ways a candidate might fail, to how a commonly-used framework might not be a good fit, to where a go-to-market strategy might fall apart, Rick Song shares the pre-mortem technique he relies on, as well as other company building lessons from Square and his startup, Persona.

Rick Song is slightly obsessed with one exercise these days: pre-mortems, or the act of thinking through why a particular strategy, product idea, or candidate might not work out down the line. This isn’t a typical focus area for founders. In our experience, they’re usually an optimistic bunch, the types who spend time dreaming up big ideas and figuring out how to run through the walls that may stand in their way — more the “move fast and break things” school of thought.

‘Why would a customer not want this?’ is often a far more interesting question than why they would. When you're working on a product idea, there's a thesis for why you believe you’re right and it's really easy to constantly confirmation bias yourself into believing it’s the optimal decision. But once you can also find the counterpoint, the scenario where you’re wrong, you can start teasing out when it would start to make sense — the point at which it will work.”


Song has had plenty of experience with making things work these last few years. Since co-founding Persona in 2018, the CEO has had his hands full with the intricacies of the 0 to 1 phase of company building.

Prior to starting Persona, Song spent five years at Square as an engineer and early team member at Square Capital. It was here where he first had the insight that led to starting a company. From fraud prevention in lending, to trust and safety with food delivery for Caviar, he gained exposure to the wide range of use cases in identity verification — and saw that one-size-fits-all solutions were falling short. With low- and no-code building blocks, Persona’s platform enables customers to craft a more tailored experience.

As investors in Persona’s seed round, the First Round team has had front-row seats to this early startup journey, and we’ve come to believe Song is one of the most thoughtful founders around. And as Song shared last week in TechCrunch, Persona is at a particularly interesting inflection point — they’ve raised a $50 million Series B and are looking to double their 50-person team this year to keep up with revenue that’s surged more than 10x and a customer base that’s grown to include some big logos like Square, Postmates, and Gusto.

In this exclusive interview, Song takes time to share what he’s learned on his company building journey so far, diving deep into how he brings the pre-mortem mindset to every aspect of running Persona.

Starting with recruiting, he shares the lessons he learned — and had to unlearn — from his time at Square. Next, we chatted about why Song believes it’s not about going down to first principles, but rather studying other companies to find unusual moves and experiment with different strategies and frameworks — of course, questioning why they might not fit your business along the way. From the strategy behind Persona’s multi-product approach — including a candid discussion about the risks — to why his engineers sell, Song shares a detailed look at his go-to-market thinking.

In our view, there’s a trove of insights in here for founders or those toying with the idea of starting a company one day, but there’s also plenty for engineering leaders and hiring managers as well. Let’s get to it.


Much of Song’s hiring philosophy stems from his days at Square. “One key piece of how Square scaled this was setting up an entire ladder of how to progress as an interviewer. They weren’t putting people on the critical path of determining whether someone would get an offer or not on Day 1,” he says.

“There was an entire training process for anyone to become an interviewer and it was very rigorous,” Song says. “Then you'd start off on the interview panels. And once you got your bearings and did a fair number of interviews, you'd become a phone screener, assessing the technical capabilities of candidates on the initial calls. Usually the more senior interviewers were the really good phone screeners. And then for the folks who were incredibly predictive as to whether someone will be successful or not within the organization, they became barometers — the people at the very end of the hiring process who helped determine whether to extend an offer.”

Below, Song delves into his top hiring takeaways from both from his time at Square and building out Persona’s early team.

Rick Song, co-founder and CEO of Persona

Lesson #1: Get granular on why a hire won’t work out.

It was from those barometers that Song picked up a critical hiring lesson. “The best hiring advice I received at Square was that when you're about to extend someone an offer, you're thinking to yourself, ‘There’s so many problems this person can help us solve, they’ll be amazing.’ And this almost certainly will be true. But it's actually far more helpful to think about all the ways in which this person may not work out for your organization — who on the team they might not interface well with, the types of projects they may not succeed in,” he says.

“The first three months of any new hire is a honeymoon period that masks a lot of otherwise clear problems. Thinking really deeply about all these potential pitfalls can help set you up for success downstream and make sure that this individual is successful as well.”

Of course, every hiring manager weighs the pros and cons of candidates. But Song shares some practical advice on how to spend more time measuring the minuses. Here’s how he operationalizes this “why they might not work” mentality:

  • Write it down. “In the early days, I used to write a doc, jotting things down for myself as to who would this person work with and how would they do. These days as we’ve scaled, it’s more about coaching hiring managers to think deeply about this,” says Song.
  • Talk yourself out of it. “We ask managers to make a really strong pitch to themselves about why this person may not work out and just be heavily aware of the potential pitfalls.” There’s an important distinction here, though. “Externally to the rest of the hiring panel and the team, you should be the absolute champion for the candidate. But internally or in discussions with your own manager, you need to be thinking through what may not go so well,” he says.
  • Bias toward no if you’re on the fence. “Although saying no may feel harder, it's far better to be a little bit more pessimistic. Hiring is such a big deal when you're only 10 people — it's a 10% incremental difference in terms of the size of your team. That's enormous. So being a little bit more pessimistic can really save a lot of heartache in the early days.” This may seem obvious, but consider the strain that early-stage startups feel as they struggle to stand out in the hiring market. “It often feels so hard to hire folks. In the early days, there's so much difficulty in trying to convince anyone to join. We initially had a tendency to rush decisions and try to hire someone a little bit sooner than we actually needed them. But adjusting to be more cautious and bias toward no has paid off so much for us.”

This approach of course hinges on a crystal-clear understanding of what you’re looking for and a well-developed sense of what a candidate brings to the table. Here, Song shares his criteria:

  • How they’ll work with others: “This 11th hire has to work well with all of the first 10 people on the team. As companies scale, generally you have more pockets and groups — and problematic relationships can be a little bit more hidden away. But for the earliest stage, there’s no escaping it. Think critically about whether this individual will actually interact well with everyone else here,” says Song. “More specifically, I try to think a lot about how this candidate would interact with the top five people I expect them to work with on a daily basis. And what are core aspects of their working style? Is one person particularly process heavy, whereas the other is much more loose and adaptive? Are the communication styles fundamentally different? Does what they value differ greatly?”
  • The kind of projects they’d excel at: “If this person is more of a big idea type of thinker, could they handle particularly complex projects where there's a lot of nuances? Are they more social? Do they prefer a leading role versus a supporting role?”
  • The core motivations that drive them: “Who are they as an individual and what will really make them feel excited about being here every single day? We want to make sure that we can provide that, that this is a place they can be successful. But especially for non-technical roles, it can be really difficult to assess how a person will actually do the job,” says Song. “For most of my interviews, I actually ask very little about how they would solve a particular problem. When it comes to questions like “What was the hardest challenge you've ever faced?’ often a lot of candidates have canned answers. Instead, I focus on the incentives. What do they care about? What motivates them? What drives them? If it's an hour-long interview, I’ll spend 40 minutes diving very, very deep into what this person wants to do. What is their ideal day to day?”
I'm a big believer that if you can get to the root of someone's motivations, you can sort of work out how they would tackle many problems.

“For example, if someone's incredibly motivated by supporting others, you can usually get a good sense of how they’ll behave when there's a product launch or when a customer challenge arises,” says Song.

But uncovering motivations through interview questions isn’t easy. “I like to ask, ‘What do you want to do after this role?’ and ‘What are the most important things that you're looking for in your next role?’ For the latter, it’s common for candidates to focus a lot more on the size of the market and impact on the world. But for us at Persona, I’m heavily biased towards people. So if I don't hear that the number one thing that motivates them is people — the folks they work with, or the customers they support — I usually think that this probably isn't the best fit,” he says.

Even when Song does hear that shibboleth in a candidate’s answer, there are still deeper depths to explore. “When you say people are important in your next role, what do you mean by that? Does that mean day-to-day or long-term impact? Is it someone you can joke with or hang out with after work, or is it about being surrounded by people who are similarly motivated? Is it people who you admire versus people who you can learn from?” he says.

Lesson #2: Focus on setting the foundation and finding the glue.

It helps to have an understanding of the pitfalls you’re likely to encounter when hiring, and these lessons were hard won, Song says. “When hires haven't worked out, it usually stemmed from us not understanding the role itself nearly well enough, especially for the first person in a specific role we weren’t that familiar with,” he says.

“Early on, we had a tendency to hire much more for potential. But requirements of the company often outscaled that potential, which meant that the individual had to grow far faster than they may have even been able to, and in a way that frankly may be toxic towards their own growth trajectory. It was key to spend more time on understanding that role and doing it ourselves for a while to figure out 1) what level seniority we need to hire for and 2) whether we needed to hire someone who already understands this role deeply.”

Song offers up an example: “For our first business hire, we brought in Christie Kim, who had a lot of experience leading people and had been at a variety of startups — she knew what she was doing, which was important because she was setting the direction for sales, marketing, customer success, and much more. Whereas on the engineering side, both my co-founder Charles and myself came from engineering backgrounds, so we could really tackle a lot of the foundational pieces and bring in some less experienced folks who could grow with us.”

Part of this comes down to understanding whether it’s a two-way door decision. “On the product side, we were still trying to understand what our product is and oftentimes the mistakes that you make are much less costly. Design is also easier to mold and redesign in the early days, and we’re a B2B SaaS company so it wasn’t an absolute pillar initially. Of course, this has evolved and changed, so we’ve started hiring more and more senior folks in these areas as we’ve scaled.”

If you're trying to hire someone to lay the foundation in a function, you can't really bet on potential no matter how much they have — because everyone else will be building off the exact same foundation.

Another frequent pitfall? Missing the mark when assessing the candidate’s motivations. “When it doesn’t work out, I always look back and try to think about what I missed in terms of what this person cared about or wanted to learn. And I think we've had a couple of cases where we felt an immense alignment in terms of core things like people and culture, but we didn't effectively highlight what joining a startup for the first-time requires. There’s an immense amount of pressure, and work-life balance can be very hard to achieve, especially in crunch periods. Painting a picture of what that looks like is important,” he says.

But that’s not to say that Song’s in the “don’t hire anyone from FAANG” camp.“The vast majority of folks here at Persona actually have no startup experience and largely come from big companies. I often joke that we're an entire company of people who have never done startups, but are all trying to learn together at the same time — and I don't know whether that will be a disaster or not,” he laughs. “Hopefully it’s clear that it’s a very friendly learning environment for all of us.”

This runs counter to common wisdom that candidates from top tech companies tend to flounder on a smaller stage with fewer resources. “There are a lot of founders out there who don't have experiences at a larger company, so it can be a bit of a black box in terms of assessing an incredibly specialized candidate and figuring out if they will actually adapt to a startup,” he says. While there are risks, Song sees clear advantages.

“One, you generally have a sense of what this function looks like at scale. Because startups grow unbelievably quickly, knowing what the end result looks like and being able to plan backwards is impactful. If you've only been at startups, you've seen how it works at a smaller operation, but the scaled up portion may be far more challenging and the pace of startup growth makes it very easy to level out.”

The key is finding the big company candidates who have scrappiness in spades. “We're looking for the people who have been the ‘glue’ — the ones who plug all the holes, are maybe a bit less recognized but constantly make it work and tackle problems that no one else was really dealing with,” says Song.

To unearth these hidden gems, ask more about the larger architecture to see how they interfaced with different functions or problem areas. “The utility player type engineers can go so deep on so many different topics of the entire company,” he says. References are also a great place to mine for insights. “If you ever hear things like, ‘If you asked this person anything about the company, they knew how it worked,’ or ‘They will literally run through walls to get something done,’ or ‘They will work with anyone,’ that’s a great sign this candidate could be amazing in a startup setting.”

Candidates who filled the gaps and served as the “glue” at big companies both know what the future looks like and have the scrappy spirit that makes for a great startup hire.

Lesson #3: Think of hiring as a segmentation exercise.

“One mistake we made in the earliest days was that we tried to create an entire track for interviewing. When it was just my co-founder Charles, myself, and maybe two other people, we prematurely created an entire interview loop, with phone screens, interview problems and onsite interviews, perhaps to make it seem a lot more mature than it actually was,” says Song. “But coming from a large company like Square, often when candidates apply, there's a very high probability that they'll join you. You're an established company. They intentionally came in. And when you're a small startup, it's very different.”

Startup hiring isn't just about sussing out whether this person's qualified, but actually remembering that every single interview is also a sell.

“If you're trying to attract top talent, a ‘First, let me make sure that you're good enough’ approach creates a weird power dynamic that makes it incredibly hard to hire. You really have to start with a much more back-and-forth approach,” says Song. “Keep the early conversations casual, and make sure the relationship is more of a horizontal-like camaraderie dynamic where you look at the individuals as equal — because for these first 10 hires, it really will be more like that.”

To foster this atmosphere in interviews, Song and his co-founder focused on turning them into conversations where candidates could teach them what they do. “Given that we were so early, we didn't know how half these functions worked. Showing that vulnerability of the things that you aren’t particularly good at as a founder is important,” he says.

Vulnerability also plays a critical role in another aspect of Persona’s recruiting philosophy. “I try to think about hiring almost as an exercise of segmentation. Today it seems as if every single startup out there is talking about hiring for mission, or how they’re going to become the largest company in the world. As a result, this ‘You're riding on a rocketship’ segment of recruiting messaging is incredibly crowded. So we’ve taken almost the complete inverse approach. I often say to candidates something along the lines of:

  • We're not trying to change the world, we're just hoping to make it slightly better. And hopefully if we succeed, people never think about their personal information being lost or mishandled ever again. It's essentially removing a burden for a lot of people. Whether it's a rocket ship or not, I can't promise you that. I don't know where Persona will be in 10 years — if we are huge, that'd be absolutely amazing, and if we're still alive, frankly, that would also still be amazing. We're just trying to take it step by step, and make sure that this is a great place day-to-day for everyone here. As a founder, all I really try to index for is that 10 years down the line, if we were to suddenly go out and say, ‘Hey, there's going to be a reunion,’ we would all really look forward to seeing each other. And if that were true, I would think I've done a great job.

“And a lot of this hopefully runs a bit counter to traditional startup hiring messaging. In practice, it’s been really helpful for us, not just from standing out in the market and winning candidates over but also in reinforcing a culture of humility, a culture of really wanting to work with other folks and a culture of caring a lot more about the day-to-day experience,” says Song.

Find out what’s uniquely attractive about your company. It doesn't have to be what's traditionally attractive — there will always be a segment of the market that is under-tapped.
Rick Song with Persona co-founder and CTO, Charles Yeh


With a team assembled and a product that’s starting to take shape, the next frontier is fleshing out the strategies that will get it into the hands of customers, help the business run like a well-oiled machine, and set the scene for the company’s next play.

We’ve recently written about how a startup’s first systems tend to be overlooked, and Song highlights another neglected area: whether a popular framework or strategy is actually the right fit for your startup.

At an early-stage startup, you'll be just bombarded with advice. You'll hear that X company did Y and it was so successful, or this strategy works so unbelievably well, whether that be OKRs or frameworks for product decisioning, like jobs-to-be-done. All of this advice is correct — given the right context,” he says.

“What's much more interesting than figuring out how to execute this framework perfectly is discovering when it does not work and finding that saddle point,” says Song. This concept originally comes from game theory. “It’s the specific spot in which the decision shifts, where you were going to bet and now you’re going to fold.”

As individuals, we focus way too much on one decision versus another, but not nearly enough on the meta question of the context that would cause that decision to change.

A few variations of this framing to get your gears turning:

  • Where's the decision point where suddenly something went from not working to working?
  • What are all the criteria that have to be true to flip your decision?
  • What’s the situation in which this strategy wouldn’t be effective?
  • How do we figure out the context in which this situation would be true?

Song takes us through two popular frameworks as examples:

  • OKRs: “This made a ton of sense for Google, but that's because they were an incredibly metrics-driven company, where you could measure a millisecond in render time difference and translate that directly into company value. But if you're an early-stage startup and you're trying to figure out how to launch, that may not make a lot of sense — your metrics may not be very clear yet.”
  • JTBD: “This has been incredibly en vogue in Silicon Valley these days. If you understand your customer base, it makes a ton of sense. But if you’re super early as a startup and you think, ‘I know what the customer looks like,’ you're probably lying to yourself,” he says. “In my opinion, it’s actually important to hedge and try to target different customer segments to see where the market pulls you. Otherwise you risk making your product overly centralized in the demographic that might not make a lot of sense for your business.”
No framework is perfect. Don’t just pick the latest trend off the shelf. The question is not so much, “How do we make this work at our company?” but rather “When does this not work?”

Below, Song shares more about how early-stage startups can approach thinking outside the box, the companies that have inspired Persona’s strategy, and of course, how to figure out where it all might go south.

Lesson #4: Study other companies to source your inspiration.

“Culture can be a huge indicator of the business strategy and growth trajectory that you'll take. When you look in the Bay Area, I think 99% of companies out here are effectively cultural descendants of Google. When I was at Square, there were so many things that we did where our defense — implicitly or explicitly — would be, ‘Well, this is how they did at Google,’” he says.

And it’s not just on the engineering side. “It’s everything from using OKRs to offering free food to structuring company benefits. Of course, Google is one of the most successful companies of all time. But this has enormous ramifications in terms of how your company will grow, the types of products that it's going to build and the kind of business model it will follow,” says Song.

“This Google-esque strategy can be amazing for building mono-product companies, but if you look at a lot of startups out here, there aren't many that’ve really been able to succeed beyond that — most have a flagship product with some sort of upsell type of motion to other types of products. But if you look outside the Valley, you’ll see companies with many different entry points into their business, and I think one key piece of this is because the cultures are really divergent.”

There's an incredible wealth of knowledge from other companies that didn't descend from the Google philosophy, but founders need to set aside the time to seek it out. “There's an enormous amount of value in exploring these alternative business models that aren’t well-trodden paths,” he says. Song shares a few that he’s been personally focused on learning from while building Persona:


What he likes: “It’s a very multi-faceted platform and an incredibly complex system with so many different entry points and almost micro businesses. Tobi talks a lot about how systems-based thinking is a huge part of everything that they do, that it's not so much about, ‘Oh, if we do this, then this will happen,’ but rather ‘If we do this, how is the entire system as a whole impacted?’” says Song.

What he’s trying out: “The leap from causal-based thinking to systems-based thinking is very large. That's a really hard thing to build in culturally. As humans, we're often more wired to think about things procedurally. X causes Y causal things is just easier for us to work through. And as a result, we tend to think a lot more about the execution of something rather than the concept of it, or how the entire system works together,” he says. “Lately we’re trying to think a lot more not just about the execution of a given framework, but rather how it plays in conjunction with all of the other kinds of frameworks, processes, and ways we make decisions at Persona.”

These days it’s less and less about what’s the right decision right now, and more about systems-based thinking.

Where it might not work:

You have to make peace with the tradeoffs and the unknowns — or otherwise risk a serious case of heartburn. “You start seeing this push and pull of how you have to modify the entire equation of the company to still make this entire formula work out. What are the trade-offs I'm making? What would the evolution of this company look like two years down the line where we've really focused on this, but now we've become a bit weaker in this area?” says Song. “And any trade-offs that you make will actually emerge two years down the line.”

Just like engineering, when you build a company there are so many trade-offs that you have to make. There isn't a perfect formula.


What he likes: There are plenty of unconventional moves in Atalssian’s story — read our recent interview with former president Jay Simons for a more detailed accounting. Here’s what stands out to Song: “They built in Australia, they have dozens of products like Bitbucket, Bamboo, and Statuspage, all of which can be used independently of each other, and all of which are entry points into the entire Atlassian ecosystem. They launched a second product, Confluence, in just their second year, building their go-to-market and product innovation muscles early,” he says.

What he’s trying out: “The inspiration here for us is where can we start spinning up second product lines? We have an initial product that seems to have found some traction and we're already trying to explore alternative products that would hopefully find their entire own entry points into the market,” says Song. “We’re trying to take a much more deliberate approach of constantly testing theories and re-evaluating if we are setting up a foundation for something that could eventually be large and gradually building our way towards finding that growth curve.”

Where it might not work:

Unsurprisingly, Song applies the pre-mortem technique to his own startup. “One of the greatest fears here is that we lose focus and stretch ourselves too thin. We might fail if we can't execute at the pace that we need to. Or if this idea of synergy between our different products isn't necessarily just sticky as we thought. Or if this culture is actually non-scalable and caps out at a hundred people,” he says.

But startups are a game of chance, of course — nothing’s guaranteed. “We have effectively traded market risk for execution risk. This decision to pursue a multi-product approach started with wanting to build a VC-backable business. For myself, I didn't feel this immense confidence that this idea and the market we’re in will suddenly become absolutely enormous. But I felt if we could create a culture where we can keep building new product lines and constantly launch new businesses, then it would be possible,” says Song.  “At the very least, I feel a little bit more comfortable with that trade because the market risk one just gave me way too much anxiety.”

This mindset was also more motivating on a personal level. “It felt like this strategy would create a culture that’s much larger than myself. It wasn't like ‘Rick has a brilliant idea and then this company went off and fulfilled it,’ but rather it became a company where many folks have amazing ideas.”

My dream is that one day I walk in and I'm absolutely surprised by the things that we're working on and feel as if there was no way I could have ever come up with any of this.


What he likes: “Microsoft has one of the most diversified revenue streams in the world. From Azure to Office, from individuals to enterprise, they’ve absolutely perfected what it means to build a platform where every product has its own go-to-market strategy. It's amazing how deeply coupled product and business are at Microsoft,” he says.

What he’s trying out: “How can we have people really focused on go-to-market from the earliest days? We have smaller teams of about five people, maybe three engineers, one designer, and one product manager. And everyone’s job is to think about go-to-market,” says Song. “And it isn't just about upselling existing customers. It's about cold emailing people and trying to figure out whether this new product resonates with them without trying to sell them our verification product.”

As you spin up a second product, relentlessly emphasize go-to-market and spreading the knowledge of how to actually sell — don’t just hire an AE for that team and ask them to figure it out.

This isn’t the typical playbook in many startup orgs, but Song is a firm believer that everyone has to embody this go-to-market mindset. “Right now, I imagine that every single person on the team is incredibly tired of me telling them how important it is to understand go-to-market regardless of your role,” Song laughs. “That means engineers cold-emailing people, having some of the most uncomfortable conversations of their lives in the same way that Charles and I did when we were starting the company. It means having PMs think very hard about pricing, about what actually resonates.”

Where it might not work:

“Microsoft has clearly found a way to consistently execute on new product lines and sell them into existing customers. So you have to ask, why are other companies not able to replicate what they’ve done? What has not worked for others that has to work for Microsoft?” says Song.

“For me, product and go-to-market have to be in lock-step to make sure the value proposition of what you're building has immense potential. But while at the early stages of a startup, product and business are literally joined by the hip, as the company scales, these two functions start to divide more and more — whereas at Microsoft, they clearly seem to be much more embedded,” he says. Another area this approach can go off the rails? “Think about prioritization problems and having your roadmap be overly dictated by sales or customer success.”

Lesson #5: Focus less on first principles, and more on how it all fits together.

Of course, borrowing inspiration from unorthodox models and trying new strategies on for size can go too far — taking every aspect of company building down to the studs of first principles would slow your progress considerably.

For Song, it’s less about reimagining everything yourself, but more about finding successful strategies that are overlooked. “We're not trying to reinvent the wheel and find an entirely brand new strategy or cultural building approach that no one else has ever thought of. Microsoft has been figuring this out over the last 40 years, the folks at Atlassian for more than a decade,” he says.

“If you're building an NBA team, it's not about finding five All-Stars, but rather five synergistic players who can really play off each other,” says Song. “The same applies to building a business. It's about finding different pieces, not trying to figure out the perfect thing that this great company did. Instead, try to think more holistically about how all of these parts interact and experiment with how this cultural value or how this operational strategy will play out within your startup.”

I think the one thing that we've consistently found true when it comes to building a business is that almost anything can work. It's more about how all the pieces are put together than trying to find the best piece for everything.

This article is a lightly-edited summary of Rick Song's appearance on our new podcast, "In Depth." If you haven't listened to our show yet, be sure to check it out here. Cover photo via Unsplash / Miikka Luotio.