, a new company in the data analytics space. While their prospects seemed bright, their timing could have been better — three days later, Lehman Brothers collapsed.

Their startup set out on a journey with just about everything working against it: inexperienced first-time founders, a crushing economic environment and a big bet on where the industry was heading. The path was twisty and full of challenges, but by 2016 the duo had amassed hundreds of customers and RJMetrics was scooped up by 

“But as exits go, it was more of a base hit than a home run,” says Moore. “The most valuable thing we took away from RJMetrics was the muscle of how to fight hard and the painful lessons that came from surviving a turbulent environment — only to later lose the long game. Take our old competitor 

 last summer for $2.6 billion. They ate our lunch, even though we had a four-year head start.” (For more of the nitty-gritty details on where things went south in their battle against Looker, check out Moore’s 

That’s a mistake Moore vowed not to make again. Equipped with a sharper vision and nearly a decade of experience, he and Stein spun off their second company, 

, using technology they retained in the RJMetrics acquisition. In just two years, they netted a far better outcome when they sold to Talend in 2018 (with only 30 employees and no outside funding). Now, Moore’s on his third venture — and he’s swinging for the fences. His current startup, 

, is a platform that aims to help companies build more valuable partnerships through data-driven collaboration. Buoyed by industry tailwinds and 

, he and his team seem to have plenty of runway ahead.

While First Round invested back in Crossbeam’s early days (and coincidentally, Looker’s as well), that’s not the reason why we were eager to talk to Moore here on the Review. With multiple startups under his belt, he’s a seasoned company builder — one who has cut his teeth as a first-time founder during some tumultuous times.

“With my first startup, we survived the 2008 downturn and got to an exit, which is more than many startups of that vintage can say. But I was so heads down focused on that ‘grinding it out’ mentality that I over-indexed on it when the time came time to push for growth — and we got lapped by the competition. 

There's a difference between building a company that survives and one that thrives, and it took me too long to adjust when it was time to switch gears

,” says Moore. “Now it seems like the pendulum is swinging back around again to a 

 mentality. Building a resilient company might be coming back in style, but this time I’m not taking my eye off of the upside that comes after.”

In this exclusive interview, Moore opens up about what he’s learned after more than 12 years in the founding trenches, from building in bear and bull markets to avoiding “meh” exits and tackling the fickle nature of product/market fit. Moore compares his experiences across multiple startups to cull together a collection of seven lessons — the ones he wishes someone had shared with him back when he was treading choppy waters as a first-time founder.

1. A strong long-term vision will help you weather intermittent storms.

To start, Moore stresses that no amount of agility can replace a strong company vision. “A good vision means you have strong first principles. The products can evolve. The team can change. The market could hit a downtown. But if you are relentless and consistent in your pursuit of a well-formed vision, you'll be able to weather most storms," he says. "The difference between having a crisp vision and muddling through without one will alter the trajectory of your company — I’ve been on both sides of that coin.”

RJMetrics was an example of the latter. “We could see an area of opportunity when we got started, but we didn’t actually have a clear vision for what we were trying to build and why it would succeed. We had one word — data — and the rest of our ‘vision’ could twist and turn based on the most recent thing we heard from a lead or customer. A strong vision could have been our backbone, but we just didn’t have it. That was no way to build a category-defining company,’” he says. “Because we weren’t steering with a solid strategy, we pursued all these product micro-optimizations and landed ourselves in a place where we created a company that creates 

Stitch was a different story. At his and Stein’s second company (the one that bagged a better exit), Moore says they had a vision from day one. “Our vision was fully baked when we stepped up to the plate. We said, yes, there's a problem space, but more than that, we have a very specific point of view on how the problem should be solved. It wasn’t just that people were feeling the pain of scattered data, but that we actually had a vision around a solution that would also fit into the market dynamics at the time, specifically how massively scalable data warehouses like Amazon Redshift, Google BigQuery, and Snowflake were coming onto the scene,” he says.

“Plain and simple, here’s the formula you need to nail down: 

Here's what we’re here to do, here’s why we'll be the best at doing this very specific thing, and here are the tailwinds that make now the right time to do it

. We’re seeing this now at my current startup, Crossbeam, too. We started this company with an extremely specific vision for what the world should look like when this data collaboration problem is solved in the best possible way, not with something generic like ‘Partnerships are a pain, let’s go figure that out.’”

What are we going to do? What is our unique vision behind it? That’s an existential, table-stakes prerequisite to building a resilient venture-scale company. Even with the best team in the best market, you’ll hit a ceiling without these ingredients.

2. Product/market fit doesn’t mean you’re in the clear.

Getting to product/market fit quickly is often seen as a panacea for startups, but Moore has learned it's not enough to simply find it — you have to keep it too. “

You can’t survive a downturn by shutting your eyes and grasping onto your product/market fit for dear life. Shifts in the market make it even more important to be at the wheel and keep your eyes on the road

This was the trap Moore encountered at RJMetrics. “

Often people talk about product/market fit as if it’s a video game level you unlock and then it’s smooth sailing from there

. That’s a mistake too many founders — myself included — have made. When we started RJMetrics in 2008, I’d say we were ahead of the market. SaaS was still barely a thing, and no one was doing what we were doing. We iterated for four years, onboarding early adopters and building a nice little bootstrapped business,” says Moore. 

“And then all of a sudden, the market caught up to where our product was. And that's when we had a crazy product/market fit period. From 2011 to 2013, we couldn’t keep up. The leads were falling off the desk. We couldn’t hire reps fast enough. It was almost unexplainable. We exploded in growth and size, so it seemed like everything was on track. But during that period, we barely changed the product. We became inflexible. The market was moving, but our product wasn’t. So by 2015 or 2016, the market had moved out ahead of us, except we didn’t see it. We kept executing — and got left behind.”

Product/market fit isn’t a diploma you hang on your company’s wall. It’s a moving target that you constantly have to monitor. Take it from me — you can find it, only to watch it slip through your fingers.

Product/market fit is the gap between the product that you built and where the market is at any given time.

 Picture a chart with time on the X-axis and progress on the Y-axis. Your product and the market are two separate lines with different slopes that move over time. At RJMetrics, they intersected at this beautiful moment, which enabled us to build a lot of value. But then we lost it. If you go long enough without changing the slope of your product to keep up with the market, they will just drift further and further away.”

3. Looking for your biggest competitive threats? Follow signals, not noise.

While understanding your competitive landscape is important, Moore’s come to learn it’s not nearly as crucial as double-checking your company’s path and course-correcting if you fear you’re adrift. 

The best way to build resilience is to stress test your own assumptions constantly

This might be a surprising takeaway — after all, given the history, you could forgive Moore for being extra wary of competitors these days. But in his view, RJMetrics didn’t get lapped by Looker because they weren’t paying enough attention to their competitive landscape — they were paying 

, we didn’t even consider them to be our competition. But fast forward six years, and my co-founder and I are scratching our heads about 

“We spent so much time spinning our wheels looking at noisy CEOs and big incumbents. We always had our eyes peeled for that next Y Combinator upstart that would come along and threaten our market position. But in the end our biggest competition came from a group of modest, hard-working operators whose experience gave them a sharper vision,” he says. “For all the young iconoclasts on Twitter, there is an equal number of quiet experts who pose more credible threats. Those were the founders who ended up taking home the gold medals in our industry while we settled for bronze,” says Moore.

The reason they ended up on that lower podium? “We got so heads down in executing on what we thought was a good idea in 2008 that in the course of those next eight years, the ground shifted underneath our feet. This entirely new way to approach the problem came forward,” he says. “I was worried about companies like GoodData and Domo, the ones who were basically doing the same thing we were. What we failed to realize is that Looker was serving the same audience on the same value proposition, with a more appealing product approach. 

We built the proverbial ‘faster horse’ while they were busy inventing the automobile

I don't worry about competition, I worry about my own vision being wrong, which creates an opportunity for competition to succeed. If anything, I think we spent too much energy thinking about the noise everyone else was making and not enough thinking about our own place in the real market.

“To get more tactical, I found it’s helpful to harness that nervous energy and channel it toward something more productive,” he says. “For example, later on in RJMetrics’ timeline, we started asking ourselves a simple question: 

What's the new product that would terrify the most us if it were launched tomorrow?

 Our answer was something that could connect the dots between all these new cloud data warehouses that were taking over the market and the emerging tools like Looker that provided a better user experience for analytics. That product would be the missing link in a value chain that would completely disintermediate RJMetrics. Rather than wait for it to show up and finish the job that Looker had started, a small team at RJMetrics built it as a hackathon project. That product ultimately became Stitch, which we successfully spun out and built into a substantial standalone company after RJMetrics was acquired.”

Resilient founders don’t ask “Which competitor are we scared of?” Instead, it's “What fully-formed company would be an existential threat to us, whether it exists or not? And if it doesn’t exist, why aren’t we building it?”

4. Resiliency starts at the top — and it's not something founders can outsource.

While navigating the rough waters of finding a vision, external conditions and product/market fit at RJMetrics, Moore leaned on what he thought was sage startup wisdom: Don’t go it alone. He turned his attention to hiring executives to help round out the leadership team.

“We burned through two VPs of Sales before we figured out that it was product issues — not sales fortitude or go-to-market execution — that was holding us back. So we set our sights on finding the perfect VP of Product to solve our product woes. After months and months of recruiting, onboarding, and testing, it turned out the problems with the product were rooted in the vision of the company,” he says. “We were right back at square one. I wish we’d spent all that lost recruiting energy working on the fundamentals of our vision so those awesome people could have had a better product to build and sell.”

There's a difference between delegating and absolving yourself of responsibility. Don’t let that new, fresh-faced exec be a crutch that causes you to ignore your responsibilities as a founder and CEO.

“As the founder or CEO, you can’t slap on blinders for key aspects of the business. 

You’re in really, really dangerous territory if you assume that anyone is going to show up and magically fix your functional problems

. When you pin your hopes on someone coming in to fix it, what you’re doing is absolving your responsibility to help crack that problem and removing all your institutional knowledge as a CEO. That’s a huge mistake.”

For example, if you’re a technical founder 

, don’t just wash your hands of this function because you hired someone with experience. “Even if you have no clue how to execute a marketing campaign, you don't know all the acronyms of online ad buying, and you don't know what looks good, you’re not off the hook. You still need to build expectations around what they will deliver, a culture that inspires them and the credibility to hold them accountable. You can’t do all that from a distance, especially with a small team,” says Moore.

It’s impossible to outsource the hardest parts of being a founder. Investors and senior hires are not a dumping ground for your tough decisions. No one’s coming to save you.

built all of his companies outside of Silicon Valley

, you might expect him to be firmly in the remote work camp. But that hasn’t always been the case. “My first job was in finance where facetime is everything. That was ingrained in my work habits, so I spent the early part of my career as a founder demanding everyone be in the office,” says Moore. “

But I’ve also had the experience of taking out a multi-year lease on an office space that outlasted our company

 So over time, my mentality changed drastically.”

Moore notes that the cloud-based tools of 2020 are light years ahead of where they were when he started his first company. “The conventional wisdom as recently as five years ago was that you’re either all-remote, all-office, or you’re doomed. That’s changing along with a new generation of collaboration tools and mentality shift among modern workers. Crossbeam is a ‘remote-friendly’ hybrid that keeps office space available for local employees but also has a large remote workforce,” he says.

With unpredictable global events like the outbreak of COVID-19, the trend toward remote-friendly and remote-first workplaces will only continue, Moore says. “It adds to your company’s resilience — whether that’s an economic downtown, office space troubles or an intense travel schedule. When we switched offices early in our journey at Crossbeam, we asked everyone to work from home for a week and faced minimal disruption. Or when we we sent our team to conferences all over the world, we knew the work will still get done because they had that remote-friendly working habits already. Physical location doesn’t cause a gap in efficiency for anyone, and that’s by design.”

The key to making this work all year round is to go all-in, even if some of your team members return to showing up to an office. Here’s a peek at Moore’s remote-friendly playbook, designed to scale, but applicable for teams as small as two:

• Zoom links are required for every meeting by default, and there can be no assumption that your attendees will be there in person, even if they are regularly in the same office as you. Showing up virtually does not require an apology or explanation.

• Make your remote team members first-class citizens. If a benefit, perk or experience is created for your in-office team members, find a way to create parity for those who aren’t in person. That means mailing items given to your in-office team to remote workers — or if you cover lunch for your in-office team, send your remote team a gift card or stipend for food delivery.

• If your leadership team has a tendency to work in company offices, make it a point to have them attend some meetings virtually anyway, especially for big company events like All Hands meetings. "We’ve taken meetings in different conference rooms or worked from home for part of the day to make this happen," says Moore. "This helps them build empathy for the remote experience and develop the sense of inclusion for remote team members."

• Find the places where shoulder taps and overheard conversations are a convenient crutch, and make them obsolete. “This means you need clearly-measured and communicated goals (we use OKRs), repositories for company history and curiosities (we use a #founder-ama channel in Slack), and 'where you need it, when you need it' repositories for key shared knowledge (we love fellow Philly company 

6. Assemble your wishlist of would-be acquirers — and start building authentic relationships ASAP.

“It’s a founder trope to say ‘we didn’t start this company just to sell it’ — and we used to say that a lot,” says Moore. “But we drank so much of that Kool-Aid that we found ourselves scrambling when selling became our best option. 

We failed to cultivate relationships with potential buyers from day one,

 so when a high-pressure offer came in, we didn’t have the time or the network to spin up a competitive process fast enough. We may have left some serious value on the table as a result,” he says.

“My co-founder Jake Stein nailed this at our next company, Stitch. He cultivated relationships with the CEOs and heads of corp dev at all of our target acquirers from day one. When we found ourselves in a similar situation with that business, he spun up a fast and efficient process that gave us conviction that we were choosing the right deal for our company and our team,” says Moore. “Now, I’m using Jake’s playbook again at Crossbeam.”

“You don’t kick things off by saying, ‘Hey, you might buy me one day.’ You cultivate them by genuinely looking for synergies between what you're doing and what these other companies are doing. That might be a product integration, it might be go-to-market partnerships. It might just be information sharing. But those relationships require a genuine — not manufactured — motive to take hold. They don’t come together overnight.”

7. Turn self-care into a strength to bounce back from failure.

A disappointing exit or a series of tough scrapes can cast a long shadow on your next play. “When you get beat, when your strategies aren’t working, when you have to do layoffs, when you announce a modest acquisition — it’s easy to hang your head,” says Moore. “It’s not exactly confidence-inspiring to see your first venture go somewhat quietly into the night. After the modest RJMetrics outcome, I was questioning whether I could ever raise money again. What was I going to say? ‘Hey, I’m the guy who pounded his chest before, trust me this time?’ It also gets personal, fast. You think, ‘Have I wasted these years of my life?’ or ‘Is my career as an entrepreneur over?’”

As a first-time founder, it’s easy to believe that the only return on investment you get from your startup is the proceeds from your exit. “Turns out the experience was the real payoff,” says Moore. “It wasn’t until I was building my second company that I realized the upside of falling on my face so many times at the first one.”

. (He’s personally come to rely on exercise and 

.) “Don’t underplay that aspect, it’s truly a big deal,” he says. “

Sometimes the company's operational failures are actually outputs of the founder succumbing to decision fatigue. Or becoming overly paranoid or personally stressed. Or not having the energy to build the support system that they need to succeed

When it comes to bouncing back from failure, there are many factors outside of your control. But all founders are in control of being honest with themselves about what they need to operate at their fullest capacity — and that includes when (and how) to recharge.

Personal maintenance is the safety net that catches you as you’re weathering failure. It’s not just how you protect yourself when things go poorly, it’s how you focus your superpowers when things are going right.

TYING IT ALL TOGETHER: THE FOUNDER’S CHECKLIST

This last lesson is particularly top of mind for Moore these days. “I’m trying to stay conscious of how I’m susceptible to these same forces in a different way now. I’m pedal-to-the-floor with Crossbeam, but I don’t have blinders on about what it means to be building a company in the turbulence of 2020. Business fundamentals are as important as ever, and legitimate product/market fit is still the most important input to making those fundamentals scale,” he says. “That long shadow of my previous experience is still there. I'm also a little older now. I have more gray hair and I've got a beautiful daughter at home who deserves a dad who is present and reliable, so I don’t have time or energy to waste,” he says.

That’s not to say that repeat founders don't make mistakes anymore, it's that you get to make a whole different class of mistakes

 — including the risk of living in the past. If I had to summarize what’s different now with Crossbeam, it’s that I have more confidence in the basics. More than a decade of muscle memory makes a subset of my day-to-day decisions a bit less fatiguing, leaving more mental energy for looking ahead to uncharted territory.”

To distill all of the work it took to get there, here’s a quick checklist of the resilient founder lessons Moore’s picked up over the years:

• Sharpen your specific product vision instead of tackling general problem spaces. Be able to answer these questions: What specific thing is your company here to do? Why will you be the best at it? What tailwinds are at your back?

• Remember that hitting product/market fit doesn’t mean you're golden. Keep careful tabs on the changing slopes of the market and where your product is — or isn’t — meeting it.

• Take note that your biggest competitors can come from surprising sources. Focus on your place in the market to make sure you’re not creating an opportunity for others to succeed — and ask why you’re not building the competitive product that’s keeping you up at night.

• Learn the difference between delegating and absolving as you bring on executive hires. Don’t try to outsource the tough calls and foundational problems to new blood.

• Be cautious when it comes to long leases and try to broaden your thinking on remote work.

• Cultivate genuine relationships with potential buyers on day one to reduce the risk of FOMO when negotiating a sale on a tight timeline.

• Weather the storms of failure with a strong support system and set of self-care strategies. The most important thing is to not go away unless it’s on your own terms.

B.Moore2.jpg

Bob Moore's first brush with life as a founder started in 2008—three days before Lehman Brothers collapsed. Since he cut his teeth as a first-time founder in turbulent times, he's gone on to build two other companies. Here, Moore shares the lessons he's learned along the way, from weathering bear markets and losing out to the competition, to finding (and falling out of) product/market fit.

This Founder Built Startups in 2008, 2016 and 2018. Here’s What He’s Learned About Resiliency

 has gone on a lot of dates in the past year. No, not that kind. We’re talking about co-founder dating.

, Lin’s seen founding teams in action — and knew what she was looking for as she set out to build a company of her own. “I always wanted to team up with someone. My experiences as a product leader were strongest when I was partnering closely with an engineering leader,” says Lin. “When I left to start a company, there were a few spaces I was interested in, but I didn’t have a specific startup idea so I set my sights on finding a strong co-founder to work with.”

But she quickly found that was easier said than done. “Most of the co-founder stories I’d heard fell in this bucket of former co-workers pairing up to go after an idea. But it’s not that simple. You have to both want to do a startup — requiring similar levels of high-risk tolerance — and be available at the same time, which depends on life and financial circumstances. And once you step outside of that pool, it gets harder to meet someone,” says Lin. “I knew I didn’t want my search to be random or unfocused, so I honed my process and took my time. 

I ended up ‘dating’ six different potential co-founders over the course of a year

. Just like real-life dating, sometimes it seemed like I was going to end up alone. Eventually, I met 

 and everything clicked. Now we’re working on a new stealth company together.”

As the next generation of company builders takes shape and new founder mafias spin out of places like Stripe, it stands to reason that more co-founder stories won’t fit the traditional mold, and will instead look a lot more like Lin’s. And judging from 

, and all the “first dates” filling up coffee shops in SOMA, the carefully designed hunt for a co-founder is already afoot.

While the Review has covered co-founder considerations before, from 

getting vulnerable about painful “divorces”

, we’ve never seen a process like Lin’s. It’s a detailed, step-by-step playbook for thinking through all the potential pitfalls that can ruin even the best of co-founder relationships.

In this exclusive interview, Lin presents that rigorous approach in full, from how she found potential partners and handled early conversations to how they ideated and prototyped together to narrow in on a more specific idea. Whether you’re a proven founder working on your next play or a wannabe entrepreneur waiting in the wings, her process can add a dose of rigor to your own search for a co-founder. 

 — with 50 questions spanning across six categories — that she and other fellow founders have collaborated on to probe compatibility more deeply.  We’ll highlight a handful of impactful questions here in this article, tacking on Lin’s marginalia: her reflections on why these questions stood out, the sticking points you need to watch for, and how you’ll know when you’ve found “the one.”

But we've also included the full set (below, in a designed PDF template so you can grab and go, and further down in a Google Doc, in case you'd like to edit and add your own questions).

Want to jump straight into the set of 50 questions to ask a potential co-founder? 

50 Questions for Co-Founders.pdf

BEFORE YOU GET STARTED: COMMON ADVICE WITH SOME CAVEATS

The search for a co-founder often conjures up comparisons to dating. It’s become a well-worn metaphor because from fights to marriage to divorce, parallels abound.

“Finding a co-founder can feel like a more intense version of dating. One key difference though is that most people have at least some experience with real-life dating. And there’s certainly tons of self-help books for tips as well as apps that make it easier to meet people. But when it comes to figuring out how to find a co-founder, it’s hard to know where to begin,” says Lin.

 two of the most common causes of startup failures are not finding product/market fit and co-founder issues

. The former is top of mind for every budding entrepreneur, but I don’t think people consider the latter as much when they’re crafting their pitches," she says. "We just finished our fundraising process and I can’t tell you how many seasoned investors told us about how a co-founder situation blew up one of their companies. But even so, there’s not much guidance out there on how to pick the right co-founder.”

One reason for that lack of guidance is that it’s hard to get too prescriptive — after all, folks are approaching the co-founder search and company building process from different places. You could be:

• Looking for a co-founder and neither of you have an idea yet.

• Searching for a business or technical co-founder to help you execute on an idea you’ve been working on.

• Pairing up with someone you already know to find an idea.

“The advice on how to tailor your search depends on what you’re looking for. If you already have a vision for your startup in mind, then you might want to skip straight into getting to know your potential co-founder on a deeper level. If you’re going to work with someone you already know, you may want to spend extra time making sure you’re aligned on how you want to build the company,” says Lin. 

People get hung up on having either a solid company idea or a specific co-founder in place from the start, but I don’t think you need either right away

. See the white space as an opportunity to try working together and a chance to explore interesting ideas at the same time.”

When it comes to starting a company, you can figure out the right space to go after and find the right person to tackle it with in parallel. Don’t compromise on either.

Lin came to this realization after seeing the hidden dangers in pairing up quickly with an old friend. “I’ve seen new co-founders get further down the company building path and suddenly realize that, ‘Oh, we didn't ever talk about this,’ or, ‘I didn't realize that we have such opposing views on this topic,’” she says. “It's kind of like moving in with someone for the first time and realizing that they leave their socks on the floor or they don’t share your approach to finances. They have all these habits big and small that suggest you may not be such a great match after all.”

Here, Lin recommends a few additional broad takeaways to keep in mind before kicking off your search:

Take your time — but realize the clock is ticking.

In Lin’s view, one of the biggest mistakes people tend to make is not giving the process time to unfold. “You don’t want to rush into a pairing or stop your search prematurely,” she says. “

 once gave me some advice that was clarifying: 

It’s common practice to take three to six months to hire an executive, so why wouldn't you take the same amount of care to find a co-founder?

 Because that person is probably going to be around even longer. You’ll potentially work together for a decade or more.”

All too often, people jump into company building opportunities and don’t spend the time testing the depths of the co-founder relationship — which makes for shotgun marriages that carry more risk.

However, there is an important caveat to consider. “People only have a certain amount of financial runway they can survive on while they’re exploring a company. Some people can only go three months, while others could last three years. As you start to run out of resources, it can feel like a very accelerated, which is why you can end up with some shotgun marriages,” she says.

Opposites attract — but don’t dismiss overlap.

“People who are very similar in their strengths can lead to weaker co-founding situations. You want someone who shares similar values, but in terms of interests or characteristics, it’s often better if you’re different — there’s a reason they say opposites attract,” says Lin. “As a small example, my co-founder Joel and I don't share a lot of personal tastes in music and other areas that are more subjective, but we’re so aligned on how we think about company building.”

We naturally flock to folks with similar experiences, tastes, and skills, but entrepreneurs overlook founding team diversity at their own peril — it’s a huge source of strength.

However, this advice doesn’t always map onto previous experiences quite so neatly. “You can’t just glance at a resume and pass on all the ones that are too similar to yours,” says Lin. “Sometimes two people with the same background want very different things when it comes to building a startup. If they’re both PMs, one might want to focus on product, while the other person may want to stretch and get into the business side. It's highly dependent on what they 

 to do, not just what they've done before — you have to talk about it to find out.”

With that high-level advice to set the scene, let’s dig into Lin’s process — and why she recommends following one in the first place. “You need to be really intentional about how you spend your time together,” she says. “In my experience a ‘Let’s see what happens’ approach with meandering conversations and unstructured brainstorming is not as effective.”

Still, a positive outcome is anything but guaranteed and progress is often hard to sense. “

Building a startup feels like you’re standing at the start of a maze and you don’t know where the path is going to lead you

,” says Lin. “It can be frustrating because you have no idea if jamming really hard for a week will get you any closer to your goal. You don’t know if it's a dead-end. You need to put one foot in front of the other — you have to keep moving.”

And she’s found that you can cover more ground faster than you might think. “You can get a lot of data on what it would be like to be someone’s co-founder in a few weeks. I don't think that these steps are strictly linear — there's no waterfall chart that perfectly illustrates the stages as you move through them. But generally speaking, 

here’s the process I followed in a nutshell

 from your network of entrepreneurial communities.

Identify overlap through initial conversations.

 Have a few coffee chats to cover some basic topics such as: 

What’s your story? What sectors or industries do you have experience in? What areas are you interested in building a startup in? 

 with brainstorming and lightweight prototyping. The goal is to both make progress toward an idea and gain collaboration experience to see what it would be like to work together.

 separately and schedule three to four working sessions to go over your respective answers.

 or part ways. Know when to pull the trigger — and when to stop and start anew with someone else.

“The shortest round I had ended after just a couple of those initial coffee chats. It was somebody who seemed great on paper, but we didn’t mesh in real life,” says Lin. “In contrast, I spent four months working with my current co-founder to validate that we were on the right track before we committed.”

In the sections that follow, Lin gets granular on each of those high-level steps, filling in tactical advice and drawing on stories from her own co-founder search experiences.

STEP 1: FIND POTENTIAL CO-FOUNDERS TO FILL YOUR PIPELINE

“‘Where do I find people?’ is one of the biggest questions I get when people ask me for advice. There isn’t a ‘Tinder for co-founders’ app that everyone is on. Sourcing is hard,” says Lin. “There were times in my process where I flipped back to working on an idea on my own because I didn’t have another potential co-founder lined up.”

Lin typically courted a mix of folks that she had either known for a long time, gotten introduced by a mutual friend, or just recently met at an event. “One person was a classmate from college whom I hadn't spoken with in a while. Some were folks that I’d met through the broader entrepreneurial communities I’m a part of, like 

“I tried to engineer serendipity — I wasn't heads down hoping for someone to cross my path. I told all my friends and closer connections that I was looking for co-founders and asked for recommendations and intros. I think you have to get out of your comfort zone and try to 

,” says Lin. “More tactically, joining entrepreneurial communities and attending events are great ways to broaden your pool. There are even some early-stage investors who help facilitate some of those interactions. The long and the short of it is that you have to be open to opportunity.”

The only opportunity that should give you pause is a chance to work with a particularly close friend. “I wouldn't go as far as saying, ‘Don't go fish in that pond,’ but you need to go into it eyes wide open,” says Lin. “

 literally wrote the book on this — in 

, he explored what kind of founders are more successful than others. His research found that social connections are likely to be stable in the first six months — the honeymoon period — but become riskier over time. And even if it works out smoothly, doing a startup together will surely affect your friendship, so you have to be prepared for that.”

STEP 2: IDENTIFY AREAS OF OVERLAP TO SURFACE A QUICK NO

After finding a potential lead, schedule a few coffee chats or calls to uncover common ground — or a lack thereof. “This stage is very exploratory. Nothing’s set in stone. You’re looking for signals that it makes sense to move forward and invest more of your time,” says Lin.

 of alignment in this step. “Actively look for counterfactuals, the places where you say ‘Oh, I actually don't think we're aligned on this point.’ I had a great initial chat with one person, but we found that one of us wanted to bootstrap our company while the other wanted to raise as much money as possible. It probably wasn’t a fit, so we didn’t need to keep spinning our wheels,” says Lin.

Here are the threads she recommends pulling on in these early conversations:

What kinds of things are you excited to work on? What have you explored recently? Are we interested in the same industries and business models?

 “Of course, your idea can change completely. Co-founding pairs pivot all the time, but you often move into an adjacent space, so it’s helpful to get a mapping of what you're respectively interested in,” says Lin. “With each of the six potential co-founders I dated, I explored different areas: identity, recruiting, interior design, security, crypto. What’s interesting is that some ideas morph and take on a totally different direction, while others don’t work out with one person, but end up making sense with someone else later. For example, I’d previously explored interior design with someone else, but now my co-founder and I are building something in the adjacent construction space.”

Are we interested in potentially exploring a co-founder relationship together? What would that look like?

 “This isn’t a negotiation over who wants to be the CEO. It’s more of a ‘In an ideal world, what are you imagining?’ kind of discussion,” she says. “There's a rough sense of roles but it's not super clear cut. It’s more like ‘I could focus on product and marketing and you could work on the tech and operations.’”

STEP 3: SPEND TWO WEEKS PROTOTYPING TO SEE IF AN IDEA HAS LEGS

After spot checking for initial alignment, Lin dives straight into tackling a project with a potential co-founder. “The first or second coffee chat may not tell you that much. But once you start doing some kind of project, you get so much more data on the person and their work style,” she says.

“For me, this was the fun part. It’s about getting your hands dirty, digging into a space, figuring out the need, and seeing if a startup idea has potential,” says Lin. “It’s also an opportunity to uncover if you’re 

 interested in a certain area. A few times I thought I was passionate about a certain industry, only to discover through hands-on projects that I actually didn’t enjoy it.”

It’s not about tinkering aimlessly, though. Lin suggests timeboxing this exploratory period to about two weeks to maximize both learning fast and moving quickly. She’s also looked to other frameworks for guidance. “I was inspired by 

Nat Turner’s approach to finding a startup idea

,” says Lin. “He and his co-founder refined them so successfully — and quickly — that they were able to start a company in healthcare without domain expertise. I had their process in mind each time I was ideating.”

Here’s an overview of targeted tactics to use when exploring an idea with a potential co-founder, the very same ones Lin used to test six different startup ideas of her own:

Explore consumer and enterprise startup ideas differently.

When investigating a consumer play with a potential co-founder, Lin is a firm believer that you have to try to build something. “It doesn't mean that you have to build a full production-ready app. Figure out the cheapest possible thing, the crappiest MVP you can get out there within a week or two just to see how things go,” says Lin. “That could be a really janky prototype, a small Chrome extension, or a landing page. Anything where you can put it out into the world and see if there’s a response.”

Contrast that with enterprise, which is more about customer discovery. “With enterprise, building often isn’t the hard part. It’s all about selling. You need a shortcut to figure out, ‘Am I making something people want?’ Do a bunch of interviews with experts or potential customers to find out. Customers will tell you what their problems are. If you listen very carefully, you might be able to figure out a jumping off point to build a company around.”

When you’re exploring enterprise startup ideas, you have to get out and talk to customers. My co-founder and I got ideas from those conversations that I could have never come up with on my own in a million years.

Here’s a sampling of the specific questions Lin and her potential co-founders asked in these customer calls:

• How do you currently manage this process?

• How big of a pain point is it for you, compared to other pain points you have?

• If you could wave a magic wand and have that problem go away, how would that affect your work or your customers?

Use these clues to find out if you’re onto something.

Of course, with time constraints and minimal resources, you can’t expect statistically significant insights from this discovery stage work. That said, there are indicators that you may be on the right track. 

“On the consumer side, a good signal is if some people tell you they want it, if you see others actually using it and maybe even actively badgering you for more. 

. They launched an open source analytics library with a landing page and it blew up on Hacker News,” says Lin. “With enterprise, it’s about looking for patterns. You need some minimum number of people in a segment saying, ‘Yes, I want this, I’d pay you for this and here’s how much I'd pay.”

“This ideation stage was where most of my ‘breakups’ happened,” says Lin. “It’s a good litmus test for whether the partnership can work. Obviously, a lot of ideas you generate together aren’t going to work out. With the right person, you can push through that, and move onto other areas and experiments. 

But sometimes when ideas die on the vine, the partnership can lose steam

. You start to question if this person is the right partner for you. Other times, a business idea had true potential, but we discovered that we had incompatible working styles.”

In Lin’s experience, these break-up conversations can be handled several different ways. “I was ghosted once,” she laughs. “With others, we had in-person convos or phone calls. There are lots of ways people can decide not to work together, but for me personally, I most appreciated when there was a clear go or no-go date, and we had one or two direct conversations about the viability of us working together. Those are the relationships I feel better about today.”

Have the courage to talk about these potential partnerships directly, especially when it's not a fit.

Once you have a very basic sense of how prototyping is going, the next step is to tackle the finer points of what the co-founder relationship might look like. Enter 

, the getting-to-know-you gauntlet that Lin throws down before seriously considering starting a company with someone.

the Google Doc version of the questionnaire

 if you’d like to edit and add in questions of your own. Want to grab the list Lin used and go? Below you’ll find a handy template, designed to make it easy for you to quickly share with a fellow founder you’re considering teaming up with:

As with most things in life, timing is everything. “Some folks are open books and they’ll do it immediately, but for others, getting into this stuff seems way too personal,” says Lin. “Out of the fellow founders I’ve known who’ve used the questionnaire, they’ve all brought it in at different times based on what they were looking for in a partner.”

If you’re looking for a co-founder and an idea in parallel

, you might want to use the questionnaire before you get into prototyping. “One pair I know wanted to understand each other better before investing time in ideation and business development,” says Lin.

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