The 30 Best Pieces of Advice for Entrepreneurs in 2023

The 30 Best Pieces of Advice for Entrepreneurs in 2023

It’s the first week of the new year, and here on The Review we’re ushering it in with a beloved annual ritual (that we find to be much more delightful than other yearly exercises like annual planning or performance reviews).

It’s the first week of the new year, and here on The Review we’re ushering it in with a beloved annual ritual (that we find to be much more delightful than other yearly exercises like annual planning or performance reviews). Before powering full steam ahead into 2024, we press pause and leaf through every article we published in the past year, plucking out our favorite snippets of company-building wisdom. 

It’s actually been a double dose of reflection for us recently — a few months back, we celebrated The Review’s 10-year anniversary with a special compilation of the 100 best bits of advice ever published in our decade-long history. (If you missed it, we highly recommend diving into this trove of wisdom.)

As we assembled that massive guide and revisited the hundreds of articles in our archive, we were reminded of all the ground we’ve covered since The Review’s inception in 2013. Stepping back to apply a decade-long lens, we concluded there’s no one singular topic or theme that makes something “Review-y” — just a focus on finding the sharpest folks who can deliver standout tactics and fresh frameworks that you can use today to change your company and your career. 

But when you zoom in on a specific year, themes inevitably start to emerge. In 2020, it was (of course) advice for navigating the tumult of “these unprecedented times.” In 2021, there was an itch to try something new, as job-seekers pursued new opportunities and funding rounds came together at lightning speed. And just as quickly, the tides turned again in 2022 — with folks facing down uncertainty around layoffs and market corrections.

Many years from now, when we look back on 2023, we will no doubt remember it as the year AI became mainstream. With ChatGPT thrusting us into the generative AI revolution, we explored some of the most pressing questions for startup operators with expert interviews on our In Depth podcast. Here’s a sampling: Bard’s Senior Director of Product Jack Krawcyzk took us behind the scenes of how Google rapidly built its experimental AI tool. Vercel founder and CEO Guillermo Rauch shared his take on how AI will transform front-end engineering, while Runway’s CTO Anastasis Germanidis outlined his playbook for planning a roadmap at an AI startup amidst rapidly-evolving technology. 

Just as the breakneck pace of advancement kept founders on their toes, the quest to find product-market fit also became more urgent in 2023. Follow-on funding became more difficult to secure and the pressure to hit metrics and operate more efficiently started to sink in. To help steer builders staring down this seemingly insurmountable climb, we set out to collect stories from founders that cleared this hurdle with our recurring Paths to Product-Market series.

We sat down with remarkable founders like Laura Behrens Wu of ShippoDavid Hsu of RetoolBryant Chou of Webflow, and Christina Cacioppo of Vanta (along with over a dozen others) to get the unvarnished story of how they went from 0-1 and found what we’re calling extreme product-market fit. With present-day billion-dollar valuations, we pushed past those shiny, up-and-to-the-right company trajectories, and dug into all the false starts, blips and moments of sheer grit that powered these unicorns forward. 

Our hope is that these stories served you well in these past 12 months, regardless of whether you were looking for inspiration for your startup’s journey to product-market fit, advice on how to build product in a post-LLM world, or frameworks for handling the past year’s challenges (such as a guide doubling down on retention and customer success, a primer on M&A, or pointers on how to shift gears from a BigCo to a small startup).

With that in mind, we present our collection of little tactics, resonant reminders and operating principles to guide you in the following roundup of the 30 best pieces of advice we heard in the past year. Take them with you as we’re thrust forward into all that 2024 has ahead.

1. Hit refresh on your interview questions for manager candidates 

Spotting folks who can become high-impact leaders at your company is exceptionally challenging in an interview setting. While you can probe IC skills with a coding test or other function-specific take-home projects, unraveling all the nuances that go into managing people can be incredibly tricky — especially with just a narrow sliver of time with each candidate. 

So we put out a call to some of the sharpest folks in our network for their best interview questions for management positions and assembled their responses into a new can’t-miss guide for hiring managers. Our goal? Give interviewers a fresh slate of questions to lean on, rather than resorting to the same ho-hum questions like “How do you describe your management style?” or “How do you motivate your team?” It was clear folks were clamoring for a fresh set of interview questions — the article with the full list turned out to be our most-read of the year.

Here are a few highlights: 

Tell me about a time when you delved into significant detail and got your hands dirty. - Gokul Rajaram, product leader at DoorDash

Walk me through the most significant change you’ve made as a manager in response to feedback you’ve received about your leadership. - Russ Laraway, author of “When They Win, You Win”

What dashboard do you open up every morning? - Alex Kracov, co-founder and CEO of Dock

Who on your team would you be happy to work for? “We all know the popular maxims: ‘Hire people you would work for,’ or ‘A players hire A players, and B players hire C players.’ This question gets at whether or not a leader actually lives by those principles,” - Brie Wolfson, former marketing leader at Stripe and Figma

Tell me about a time when you influenced another team in the company that had a diametrically opposed point of view. Ravi Mehta, CEO of Outpace

Why did you leave IC work? - Farhan Thawar, Head of Engineering at Shopify

What processes have you put in place to ensure that each person on your team has a clear idea of the team’s goals and their own role and responsibilities? - Liz Fosslien, Head of Storytelling for Team Anywhere at Atlassian

2. Set goals by trying to tell a story 

You can't copy-paste your bigger company frameworks when you join a small startup. But zero process isn't the answer either. Take goal-setting as an example. 

"Managing a large team is a very detail-oriented exercise. You’re looking at headcount and schedules on a long runway, and that’s impossible in a startup setting. But too many early-stage teams opt to skip over planning and goal-setting altogether," says James Everingham, who jumped from big to small when he moved from Meta to co-founding Lightspark.

To hit that target Goldilocks, just-right amount of process, borrow his concept of “management by narrative.” Don't drill straight down into specific KPIs and targets — start by trying to tell a story. "Begin with a thesis, such as ‘This is what we're going to do this year.’ Break that narrative up into chapters, almost like titles. The flow is, ‘First we're going to do this, then we're going to do this, and then by chapter three we’ll have done this, and chapter four is the end, where we have product-market fit and we're scaling,’” he says.

James Everingham's template for management by narrative
James Everingham's template for management by narrative

But here’s the key for an early-stage startup: "As we’re building our plans, we only focus on those first three months, that first chapter. So we break that down into monthly high-level goals, and that's what I hold the team accountable for,” he says. In other words, don’t try to get detailed for longer than a few weeks out. "At a startup, it’s almost assuredly wrong past that. All you can do is make sure everyone knows the story, the short-term outcomes you're looking for and that they're doing work that maps up to support that.”

I like to go through every single thing the team is doing and ask: If this one thing weren't done, would we not be able ship the product? And if the answer is, ‘No, it would still ship,’ then it's off the list.

Headshot of James Everingham
James Everingham, SVP of Engineering at Lightspark

3. Opinions come at a cost — spend wisely 

As a founder, you’ve built the company in your own vision — and in the early days, you have immense influence over every single facet. But as the company grows and you bring on more manpower, suddenly your influence starts to shrink. 

But far too often, rather than empowering these super-sharp folks who have been hired to make their own well-informed decisions, founders continue to make sure their opinions are heard loud and clear. But foisting your opinions on others can do immense damage to your workplace culture. Not only are you potentially wrong (because even founders and CEOs can error), but even if you’re right, it’s a risky move. 

At the helm of an entirely async company, Sidharth Kakkar, founder and CEO of Subscript, has had to carefully root out any of his own micromanagement instincts. He flags a couple of sneaky outcomes from being too free-wheeling with your opinions. 

Employees lose confidence in their skills. “You’ve squashed their creativity and you’ve squashed their ownership chops.”

Employees become more concerned with your opinion than finding the right solution. “You want to avoid folks thinking through problems like, ‘If I don’t do things Sidharth’s way, then that means he’s going to think less of me.’ Which is quite detrimental to the business.”

Employees become dependent on you to make decisions for them. “Then you condition folks to think, ‘I better just run all my decisions by Sidharth.’ And that is the worst possible outcome that you could imagine.”

No matter where you work or what role you’re in, you can use Kakkar’s advice to weed out your own micromanager tendencies: Before you give an opinion, ask yourself, “Am I right or do I just have an opinion? If I am right, what’s the cost of being right?” You might discover what you have to say is better off left unsaid.

Anytime you’re telling someone what to do you’re not actually solving the bug. You’re doing a really bad patch.

4. Balance the core product with new bets by looking to the horizons 

Once you find product-market fit the first time, a new challenge appears: How do you juggle improving your existing product with growing your business? You could maximize your core product, pouring resources into tinkering and perfecting it — yet, by doing so, you miss out on seizing new opportunities while competitors creep in. Or you could pursue innovative ideas at the risk of devaluing your revenue engine.

That’s why Shippo’s founder and CEO Laura Behrens Wu uses the Three Horizons framework to balance bigger product bets, as she explained in her Paths to Product-Market Fit installment.

Horizon One: Core product (70% resource allocation). “A Horizon One product is one that’s working really well and is the core part of your business, probably the majority of your revenue. It's all about optimizing Horizon One and making it work better and building this revenue engine. But you don't want to take too much risk here because it’s a more mature product.”

Horizon Two: Forward-looking products (20% resource allocation). “Horizon Two and Horizon Three products are forward-looking. You don't have product-market fit in those products just yet. Horizon Two is where you have a good hunch that there's something there, and it'll work.”

Horizon Three: Big risks (10% resource allocation). “Horizon Three products are insane ideas, and you're just dabbling. You have no idea whether they could be some business line in the future. A Horizon Three idea might mean playing around with how you can implement Generative AI into your product.”

Don’t get so obsessed with the big shiny stuff in the future that you forget about what is actually generating revenue today.

5. Pinpoint where you’re delivering feedback as a manager 

Folks are clamoring for more feedback from their managers. But when you ask these very same managers, there’s a disconnect — they feel they’re constantly delivering feedback. “The reality is that we’re never as explicit as we think we are,” says Marcel Weekes, VP of Engineering at Figma

So time and time again, Weekes has learned to cut closer to the quick. “As a manager, it’s almost painful to say, ‘I have some direct feedback from you.’ It may seem pedantic or, at some level, contrived,” he says. “So instead, we weave the feedback in among other things and now it’s watered down. It’s born from a place of trying to make people feel comfortable, but it has a very different effect — it makes people feel unsatisfied.”

It’s critical that we are very clear about positioning feedback as feedback. I want my direct reports to be able to leave the 1:1 and point to an exact sentence where they received feedback.

Headshot of Marcel Weekes
Marcel Weekes, VP of Engineering at Figma

6. Walk confidently through two-way door decisions 

As a product leader at a growing company, the decisions you make only become more high-stakes as the organization scales. Each potential change to the product impacts a wider customer base, more voices across the org chime in with warnings of what could go wrong and the risk of failure looms larger. 

It’s only natural then, for product managers to take the path of least resistance. After all, a misstep could carry painful repercussions — for customers and users, for your team's momentum and for your career trajectory. 

However, playing it safe also carries a cost. Opportunities are missed, innovation gets left on the table — and possibly the biggest blow to scaling companies — progress can gradually grind to a halt. The key, Slack’s Chief Product Officer Noah Weiss says, is to find the right balance, fully evaluating risks while not becoming paralyzed by inaction. 

One useful framework for minding this balance is to think through decisions using the one-way vs. two-way door model: 

Two-way doors: “For example, it can feel very fraught when deciding on a new tagline for the homepage. It’s very prominent and visible. You can spend months internally debating and focus group testing, and still end up with an option that no one person wants to 100% claim. But, while visible, a new homepage tagline is an incredibly easy decision to reverse. This is an example of a two-way door. Teams should feel comfortable walking through this decision knowing that making any changes or updates to the tagline will be easy to revert.”  

One-way doors: These are decisions with long-term repercussions that are much harder to reverse. For example, changing the name of a core product. Once product leaders identify an upcoming decision as a one-way door, Weiss encourages giving yourself enough time to work through what the biggest risks are ahead of time, so you can be more judicious.

7. “Give away your people” and prepare for high performers to leave

The cold hard truth about working in scaling companies is that people, and in most cases, top performers, are going to leave. The question for managers shouldn’t be how to prevent this natural growing pain from happening, rather the focus should shift to: What are you doing to prepare for it? 

As a longtime startup operator and leader, Clarissa Shen saw so many well-meaning managers get caught off guard by superstars moving on, that it catalyzed her to craft a new philosophy: Managers should always be prepared to give away their people, and when the time comes for a high performer to leave, Shen argues that managers will actually be better off for it.

“One thing I learned early on was managers need to have very specific conversations with reports on what they are looking for in their next growth opportunities,” she says.

Accept that people are going to leave. Especially if you are a first-time manager, it’s much easier to go into the role accepting that someone is going to leave, rather than blaming yourself when it happens.

One of the simplest ways that managers can get ahead of the blindside is to regularly take a pulse check on their direct reports’ career goals — not just during annual performance reviews. Shen offers a few low-lift tactics on how managers can do this in their next 1:1s: 

Try making every fourth 1:1 a career growth conversation. Block off at least an hour of time, allowing for the conversation to meander 

Create a unique title for the meeting. It should be separate from a weekly 1:1 and a quarterly performance review 

Come prepared to talk about your own career growth and bring examples or stories of opportunities that you’ve spotted for yourself

8. Track your mood – not just your metrics  

To cope with the wild swings of uncertainty during the hunt for product-market fit, Productboard’s Hubert Palan came up with an interesting practice. Using a spreadsheet, he plotted how he felt about the prospects of the company three times a day: morning, lunchtime, and evening, and called it his “Founder Mood Meter.” 

“I measured my own happiness as a proxy for the customer's happiness. At first, it was completely up and down. Eventually, I started feeling much better about where we were headed once the feedback became consistently more positive. It became obvious that there was a real market here — not just a few nerdy tinkerers,” he says. 

And then, it happened. “We kept building the features, and eventually, the features became good enough for the jobs, and then suddenly, it was there: hockey-stick growth.”

Graphic of the Founder Mood Meter - ranking notes from the day 1-5

9. Strip “and” out of all your headlines

CopyhackersJoanna Wiebe serves up incredibly sharp copyrighting advice, so we were thrilled to feature her wisdom on The Review this past year. As she sees it, the word “and” is an insidious "lose-money" word. "It shows up everywhere. It’s small and functional, so it seems to be friendly. But our brains don’t enjoy trying to suspend a bunch of thoughts in the air as we seek meaning or try to decide. Every time you use the word 'and,' you lose a conversion. If you insist on using 'and,' then you need to be cool with losing leads."

For an example, read each of these headlines, pausing to close your eyes, count to ten, and then try to remember the key points covered. The first headline is the easier one to remember.

Graphic comparing one headline with the word "and" against one that does. The second one is longer

​​This is because of a concept called interference, which defines our inability to recall information when we’re exposed to more than one message at a time or otherwise distracted.

If we’re going to add words to the page — and risk losing a conversion each time — we’d better use words that are not going to double-down on interference. Any word on the page needs to earn its place.

10. Inject gratification to the grind of startup life 

As a psychologist working 1:1 with founders as they ride the waves of startup life (and a founder herself), Dr. Emily Anhalt has seen firsthand that founders have a remarkable ability to delay gratification — they are uniquely gifted at putting their heads down and pushing forward without much recognition. 

But eventually, that seemingly endless well of self-assurance and motivation will run dry. “It’s hard to push towards something in perpetuity if you don’t pause and feel proud of what you’ve accomplished thus far,” says Anhalt. (As she explained in her latest article with us, this isn’t the only founder trait that’s a double-edged sword.)

And this heads-down mindset that can slowly infect the rest of the team. “Founders who don’t believe they themselves deserve recognition for small wins will be less likely to recognize their team. They’re less likely to say good job, or celebrate milestones, like raising a Series A,” says Anhalt.

A mistake founders often make is assuming that because they need less validation along the way, no one on the team needs gratification either.

Anhalt shares advice for founders to tweak their approach to inject a dose of validation energy for themselves and mete out kudos to others.

Be your co-founder’s cheerleader. “It can be very lonely to not have your work recognized — but it’s also incredibly uncomfortable to toot your own horn. I recommend that co-founders shout each other out and share with the rest of the team what the other is doing. For example, I will make a point of saying to the team about my own co-founder, ‘Alexa has been working so hard behind the scenes to secure this next round. Here’s everything she’s been doing and it’s been so cool to see her in action.’ That way the rest of the team can share in that pride.”

Make the ask. “Founders are quick to ask for constructive feedback. But I recommend they also ask for positive feedback, too. Ask your team what they think you’re doing well or in what ways they feel supported. What kind of milestones can they not wait to get to? Why are they most excited to work at the company?”

Tell folks they’re making a difference. “There’s a lot of talk about ‘the trophy generation’ and that people just need constant compliments. But I believe it’s the meaning-making generation. Folks want to know what they’re doing actually matters. If not, why are they working so hard? It’s important to help your employees understand that their hard work is being seen and that it makes a difference to the company’s goal. While it’s important to let people know when they need to make a change, it’s also important to cheer when things are going well.”

11. Learn to be an emotional dampener as a manager 

After nearly a decade managing product teams at places like Webflow, Dropbox and Airbnb, seasoned product leader Jiaona Zhang encourages anyone eyeing the manager’s seat to carefully consider if motivating a team (and all the soft skills that come with it) is something you’d enjoy taking on. Taking on emotional labor to boost your team’s morale while also massaging their frustrations requires its own unique, nuanced touch.  

“An important skill set of being a good manager is what I call being an ‘emotional dampener’ for the team,” Zhang says. “An emotional dampener finds themselves in situations where they know their team is upset, they know people are frustrated about a certain problem but choose to coach them and help them by dampening their emotions as opposed to riling them up. If that’s not an easy role for you to take on, you should think twice about being a manager.”

There's a saying that a good manager is often a punching bag and a therapist. It’s important to go into the role with eyes wide open and be aware of all the emotional hats a good manager needs to wear.

12. Hire smarter with a capacity plan

Startups have developed a bit of an allergy to over-engineered processes. So when it comes to creating spreadsheets and building models that keep tabs on a company’s future headcount plan, leaders often write this off as unnecessary bureaucracy. But when the company starts to scale, you don’t want to fall behind because you neglected to take the time to do this important strategic work.

But Richard Cho, SVP of Talent Acquisition Charlie Health, has seen the dangers of what happens when businesses start to scale without a proper headcount plan in place.

“A typical headcount forecast starts in Q3, is finished in Q4, and is finalized in Q1,” Cho says. “This means that recruiting teams — who are sometimes the last to know when the final forecast is approved by the board — can’t start responding to that forecast until sometime in the middle of Q1, putting recruiting teams months behind before they even can post a job description.”

While starting to keep track of hiring data can feel intimidating, don’t worry about creating anything fancy here, says Cho. The important thing is to get your hiring funnel down on paper, so you can get into the habit of inputting and collecting data when it comes your way.

Here’s an example of what a bare-bones capacity plan can look like for an early-stage startup:

A basic model of a capacity planning model for an engineering org

13. Figure out how much self-doubt you can absorb 

For Michael Grinichthe period between idea validation and product launch was unusually lengthy, as it was over a year before what became WorkOS made it into the hands of a single customer. But as any founder grinding away before launch can tell you, that extended time table allows for self-doubt to creep in the backdoor. 

A big part of having the grit to survive the startup process is this: How much doubt can you absorb? How long are you willing to be misunderstood? How long are you willing to be wrong, or think that you’re wrong, yet keep working on it anyway?

For other builders lost in the wilderness, he shares three reminders for not allowing self-doubt to knock you off course:

Know the difference between productive vs. unproductive self-doubt. “If you can make the concern concrete, if you can point out a specific reason why your idea is not working, that’s useful self-doubt. But if you can't really make it concrete, it's probably just anxiety or existential angst.”

It’s okay to seek occasional external validation. “Looking for bits of external validation is normal because you’re human. After we launched, we made this deck of all the positive tweets from people saying they’d love to use WorkOS. We just needed something to hold onto because we knew the feeling would evaporate in a month or two.”

Accept that self-doubt never goes away. “To this day, there's stuff that we're investing in and shipping that has very little concrete traction, but we have really high confidence that long term it's going to be extremely valuable for us to build. The things that you work on that could have huge upside all look like a big bet without much definition around the success or the ROI. But you just have to have this innate belief that it's going to work in some way.”

14. Identify your goal-setting philosophy

It’s time for your quarterly goal-setting exercise. But the new SVP, Julie, pushes back on setting an aggressive target for her team. She’s got some scar tissue — at past companies, if she sets a target and misses, it’s likely her budget that gets the chop next year. So instead of going big, she wants to opt for a modest target that she knows her team will over-perform.

While fictional, this example is all-too-real amongst executive teams, says COO advisor (and former PayPal BizOps leader) Amanda Schwartz Ramirez. “Most execs come into goal-setting with their own assumptions (and baggage). You can speak to four different leaders and you might get four different philosophies regarding what it means to achieve a goal. For example: 1. All goals need some margin for error (success = 70%). 2. Goals and plans are interchangeable – you either achieve, or you don’t (100% or bust). 3. Shoot for the moon! Land amongst the stars! (50% is a massive success). Or 4. Set modest targets and wildly outperform (150% is celebrated).”  

So, who’s right? Well — everyone (and no one). What matters most here is consistency across the team. So pick the goal-setting philosophy your company wants to aim for, publish it widely amongst the team to set those expectations, and stick with it. 

Headshot of Amanda Schwartz Ramirez
Amanda Schwartz Ramirez, COO advisor for emerging tech startups

15. Stay paranoid on the hunt for PMF 

Many describe finding PMF like a lightning strike, an unmistakable “you’ll know it when you see it” type of feeling. But it was decidedly more ambiguous for David Hsu when he was building Retool.

“We talked to someone who said that finding product-market fit was so visceral that you immediately feel it — like a geyser exploding. We honestly never felt that. Every customer we got — whether that was number four or number fourteen — felt like the last customer we were ever going to find,” he says.

The wide range of use cases for the product compounded this feeling. “DoorDash was building logistics tools for drivers. Brex was building tools to manage credit limits. And that was totally different from what a tutoring company was using Retool for,” Hsu says. “So I remember wondering whether we would actually be able to serve these customers and make them happy with so many different use cases.”

It wasn’t until the 40 logo mark and the first few million in ARR that Hsu started to feel confident. That’s why he advises founders today to stay paranoid, and keep pushing. “It’s like rolling a stone up a hill — if you stop pushing, it'll start rolling back down rapidly.”

16. Don’t fumble the bag with bad deal room etiquette

Navigating acquisitions is one of the more underexplored topics in company building — yet it became especially relevant as market upheaval had some founders reconsidering their exit strategy. 

After selling three different startups successfully, Daniel Debow has become something of an expert on the art of M&A. His most recent startup Helpful, was acquired by Shopify in 2019 and he’s worked at the e-commerce company ever since as a VP of Product. On the side, he advises several founders in his former shoes.

While the intricacies of an acquisition are unique to each company’s situation and ideal outcomes, Debow has seen plenty of well-meaning founders fumble a good opportunity inside the boardroom.”  Here are the three mistakes would-be sellers should avoid if they want a deal to go through:

Don’t inflate your numbers. “Remember that these are people that are betting some portion of their careers on you. Appreciate that,” Debow says. “If there is something you are worried about, air that out early. You’re not going to fool them into buying you.” 

Don’t be arrogant. Debow sees this the most with founders using non-standard definitions for their numbers or performance, intended to make them look better. Remember, “they don’t have to pull the trigger,” says Debow.

Don’t think the deal is over just because they said no. “A great mentor of mine once said ‘all great deals are lost before they are won.’ If a deal falls apart, that might just be the moment where you have to rally. You can’t give up on this journey. You have to be quite relentless.”

17. Diagnose your customers’ problems like a doctor 

While toying with the idea of building a startup focused on mental health, Harry Ritter spoke to around 50 therapists to get a better sense of their challenges. We were most struck by how he leveraged his medical background here, bringing the precision of a physician attempting to diagnose a patient to the customer discovery interviews that informed his early vision for Alma.

In addition to asking each person he spoke with for introductions to three more therapists, Ritter created interview guides that standardized the conversation with the same 10 questions across the board to avoid introducing his own bias. “They were built on some of the interviewing skills that I had from medical school. When you're trying to diagnose someone, you're supposed to combine both narrow questions and open-ended questions.”

Narrow questions. These types of questions grant you a structured data set you can use to think about what comes next. For example, “What application are you using for finding new patients?”

Open-ended questions. These let you capture information you may not have thought to ask. One open-ended question Ritter asked was, “What are the biggest challenges that you face in your private practice today?” “The one consistent theme that I hadn't thought about was loneliness as solo providers,” he says. “Alma’s emphasis on community and connection really came out of that insight that I hadn’t expected going into those interviews.”

18. Carry storytelling into your sales pitch 

Storytelling is one of the most powerful tools a seller has in their toolbelt. Why? Because stories elicit emotion, and most purchase decisions are driven by emotion,” says Emery Rosansky, First Round’s own VP of GTM.

We feel this sales/stories connection when we decide to purchase a new top because we like the way it makes us feel when we try it on for the first time. But for some reason, when it comes to software, folks (especially founders who haven’t come up in the sales org) tend to forget that emotions and storytelling are just as important to the startup selling process.

Whether it’s pitching to a potential investor or trying to close a deal with an early customer, one of the biggest mistakes Rosansky sees when she works with founders is folks rattling off quantitative numbers, with little (or any) time devoted to storytelling.

Is it more powerful to show a slide full of statistics on the impact your product has had across your customer base or to tell a story about a specific customer and how they went from struggling to scaling with your solution? If you said the latter, you’re right.

So look for natural opportunities to integrate storytelling into your discovery calls. “This can be the company origin story, stories about other customers who had similar challenges to the one your prospect is sharing, stories of customers who had similar objections to your product that the current prospect has (and how they overcame them) or stories of customers who ‘won’ using your product,” says Rosansky.

19. Find your co-founder ritual 

Maintaining a healthy co-founder relationship can feel like going through the motions of a delicate dance. The choreography only works if there is absolute trust between partners, and you must constantly anticipate the other person’s moves. If you don’t, the chances of you both stumbling are high. 

Labelbox’s Manu Sharma and Brian Rieger don’t take this task lightly, even five years into their co-founder relationship. As their company continues to grow, they’ve had to scale the processes that ensure their relationship stays intact and thriving alongside it. 

One of the simplest ways they’ve been able to remain on the same page is by enjoying a shared ritual. “We found that as the company scales, we spend less time looking at the same things or working on things adjacent to each other because it’s just a larger organization. So we intentionally spend many hours together on Friday every week,” Rieger says.

It’s uninterrupted time set aside for wide-ranging talks — the kind you can’t squeeze into your calendar in between back-to-back meetings. The pair worked with an executive coach to come up with a series of questions to make the most out of their shared Fridays. The first bucket of prompts is designed to evoke reflection about the company and themselves: 

What are your recent observations about the business?

What are the most important things we should be working on?

What is the biggest challenge you are seeing?

The second bucket was designed to create conversations around alignment: 

What are the big opportunities out there?

How is the market shifting?

What have we heard from our partners, customers, and advisors that we value?

“When you are in the soup, it’s a little hard to see the whole thing. These questions are designed to force you to step back and observe outside your own world, challenging the ongoing thoughts in your head that are often contextual and narrow,” says Rieger. 

Headshot of Labelbox co-founders Brian Rieger and Manu Sharma
Labelbox co-founders Brian Rieger and Manu Sharma.

20. Keep having customer conversations until you can predict what they’ll say next. 

Christina Cacioppo had a bit of a learning curve when it came to figuring out go-to-market for Vanta. “I had no selling experience whatsoever — the last thing I sold prior to starting Vanta was Girl Scout cookies.”

After exploring (and abandoning) several product ideas, customer conversations were her way through. “We decided we weren’t allowed to build anything at all. We had to just talk to people — and talk to them until we had a lot of confidence and a mental model of customers, their jobs, the problems they might have and how we might solve them,” she says.

Cacioppo’s advice here is to get into the details of their day-to-day life. “For discovery, the best thing we did was ask people to pull up their calendars. Then, we’d say, ‘Look at all the meetings you had in the past couple of weeks. What were the best parts of those past weeks? What were the worst parts? That finally got us to a problem worth solving.”

You’ll know you understand the problem when you can predict 75% of what a customer tells you.

21. Add “push the envelope” features to the roadmap 

In our series to unpack various companies’ journeys to product-market fit, one common thread has been those early-days decisions — the ones that seem small at the time but end up making an outsized impact.

Webflow co-founder Bryant Chou sat down with us earlier last year to dig into the company’s path to product-market fit, and this small observation stood out: “The most obvious things to build commercially are not the most obvious things to build from a product brand perspective,” he says. 

As a small example, one of the product’s earliest features was Webflow Interactions. The brainchild of their first employee (an engineer with a motion graphics design background), it aimed to give the platform the same level of digital authoring of video editing tools. Chou admits he didn’t really understand the importance of allowing designers to create a parallax scrolling or mouseover effect. 

But it turned out to be an inflection point that significantly elevated Webflow’s product brand among designers — and helped the company build momentum, with tens of thousands of signups after launching on HackerNews.

When I think about our product roadmap, I consider which features make commercial sense for us as a business, and which ones kind of pushed the envelope and make Webflow truly special — which aren't always the same thing.

22. Zero in on net dollar retention 

With a tricky macroeconomic environment stretching out sales cycles, this past year there was a renewed focus on shoring up existing customer relationships, not just amassing new ones.

So we asked several top customer success experts for their essential advice on bringing CS to the forefront. And when we asked them the most important metric to keep in mind during a downturn, we received a resounding chorus for one in particular: Net Dollar Retention. 

Calculated as a percentage reflecting revenue growth over time, measured by taking starting revenue, adding an expansion, and subtracting churn, NDR can offer perspective into why customer success is such a necessary function. 

Stripe’s Tim Smith explains why NDR tells a more holistic story than other popular CS metrics like churn. “Net Dollar Retention is a great construct for seeing the big picture around retention and renewals,” he says. “Churn is only a downside metric with the best possible outcome being zero churn, which will never happen even for the best product due to non-controllable factors. However, net retention is a more extensive metric that lets you include churn and expansion together. This puts your team in a growth mindset rather than focusing on downside potential.”

In times of uncertainty, customer retention, rather than acquisition, should be the primary focus. As adding new customers becomes increasingly challenging, your net dollar retention can save you.

23. Level up your strategy as you get more senior 

One risk when scaling organizations is letting strategy become a buzzword, rather than an action you see through. It’s a serious pitfall to avoid — a strong strategy marks the difference between a successful startup and a failing one. On top of leading top product teams, Jiaona Zhang also teaches product management at Stanford, so we’d be remiss if we didn’t include another gem from her on this list of advice. 

As she explains to her students, the hack to good strategy isn’t a robust Excel spreadsheet or a cost-benefit analysis comparing all the features in your roadmap. Rather, good strategy is good storytelling. 

“People tend to overcomplicate it, but it’s actually quite simple. Strategy is outlining the things you are going to do to get to where you need to go. I stress a lot around telling human stories,” says Zhang.

A good strategist should be able to say in 30 seconds what we’re doing for our users. 

As you widen the aperture and help your teams think strategically, Zhang reminds you to tailor your method to your audience.

“If you are working with a first-time PM, you are drawing a narrow box with a thick marker,” she says. “Inside the box, you are explaining the future we want to build. Outside is the goal we’re trying to achieve. As your team gets more senior, you no longer have to tell them, ‘this is exactly what you have to build.’ Instead, explaining strategic decisions turns into ‘I don't know what we’re going to build per se, but this is the outcome that we need to achieve.’”

24. Ditch your demo and replace it with a “marketing vignette” 

Instead of choosing one product idea and building a quick MVP, Material Security’s Abhishek Agrawal and Ryan Noon tested four different startup ideas by attempting to sell each of them — with no code, no demo, no prototype. 

They’d start the day with meeting an HR leader to pitch a people analytics product. The next hour, they’d go to a security person and pitch a security analytics product. And then, later in the day, they’d pitch another security product that was slightly different. “It was like a 9-to-5 job where we were trying to sell multiple different products at once,” they say.

Not only had the team not yet built a demo for any of these ideas, but they also didn’t even have a landing page or full mockups because they didn’t want to waste time on something they hadn’t yet validated. Enter “marketing vignettes.” These were pitch decks built to look like pared-down sales landing pages, with descriptions of different features. 

This tactic worked for a few reasons:

It gauged interest without overwhelming. “There was just enough UI to convey a concept without letting you get bogged down in it with a customer.”

It allowed the founders to experiment with messaging. “A big part of finding product-market fit early on is testing messaging. When you make slides, it lets you skip over product marketing because you're just thinking about bullet points that list features. But when you make marketing vignettes, you have to name your features and also convey in a couple sentences what the benefits are. It forces you to exercise muscles around positioning and marketing.”

It quickly helped the founders find out not just which ideas the customers cared about but also which ideas *they* were excited to pitch. “If you were struggling to pitch them, or if you were having to pump yourself up, it would become clear they weren’t winning ideas. But if you were energized by your own pitch, you knew you were onto something.”

See their real-life example in the image below, and read more of their tactics for finding product-market fit quickly here.

Example pitch deck with the send securely product offering embedded into an Email draft

25. In a net-new role? Slow down to speed up 

“As a company’s first head of customer advocacy, I came in understanding that this would be a blank canvas that I would have to fill. I fell into a common trap, which is rushing in full speed,” says Kalina Bryant, a seasoned customer advocacy leader who’s held roles at Asana, Talkdesk, Anaplan, Marketo (and now advises First Round-backed companies).

“Often there’s pressure to show results immediately, to launch a customer advisory board or a brand-new program in a month. But you need to make sure you have the right people in the room — being wrong is very expensive, and not just in a dollar sense,” says Bryant. 

“You could be going after the wrong customers. You might not be sure what kind of feedback you’re looking for yet. You might not have a developed-enough roadmap to even show them. You can waste time by moving too fast. Outlining the customers and business goals you’re going after might take some time, but it sets the foundation for fast, creative experiments in the future.”

26. Lean into early founder-led sales — even for a PLG product 

Even though the Merge founders Shensi Ding and Gil Feig were big believers that inbound would be a powerful channel for the integration API product’s growth, the founders still dedicated immense amounts of time to outbound selling (in fact, they did all the sales conversations themselves for the first eight months). So why sink so many hours into talking to customers when leads were rolling in organically? “We still started with a lot of outbound because there’s no replacement for that learning. You just have to reach out to as many people as possible. Founder-led selling creates a tighter feedback loop that makes your product better,” says CEO Ding.

When you do founder-led sales you’re not just learning how to sell your product, you’re learning how to tell a story. This is essential to sell the vision to investors or to candidates you’re trying to hire.

The goal was to amass a ton of learnings that they could eventually pass over to their first head of sales hire. Here’s Ding’s summary of what worked and what didn’t:

What worked: Demoing. “What always pissed me off as an engineer was going into a vendor meeting and not being able to see the product. Once prospects could see how intuitive, yet powerful, our product was, they would be much more interested in using it themselves.”

What worked: Self-serve. Along similar lines, getting customer’s hands on the product sooner, rather than later, was key. “There was no barrier to entry to try out the product and validate that yes, Merge works. And then we can come in for a sales conversation to upgrade.”

What didn’t work: Meeting with the user. “We found that talking to certain personas didn’t get us closer to a sale. Meeting with an IC engineer or post-sales folks didn’t work — we needed to meet with someone with greater buying power, like a head of product or a head of engineering.”

27. Focus on problems, not solutions by finding the parking brake 

When bringing your product to market for the first time, it’s important to understand the difference between what your company makes, and what your company sells — because these aren’t necessarily the same things. 

It may seem like semantics, but excavating this difference will ultimately help founders understand the unique offering that sets their product apart in a crowded market, according to Jonah Berger, Wharton marketing professor and author of several business psychology books like “The Catalyst: How to Change Anyone’s Mind.

Too often leaders, salespeople or founders think they have a solution, regardless of what the problem is. They don’t know whether they’re truly selling a solution, and they also don’t understand which facets of their solution to focus on for a given audience, because they aren’t grasping that audience’s needs,” Berger says. 

“It’s not until you understand the problem that you can begin to prescribe the solution. Think about doctors. They don’t say, ‘Let me put a cast on your leg.’ They say, ‘Let me understand if the leg is broken and if it is, I can prescribe a solution.’”

Here are two techniques Berger suggests as guideposts for founders when trying to diagnose their customer’s problems: 

Think of the end result. Probe deeper into what you want to change by asking questions like “Whose mind or behavior are you trying to change? What are they doing now (i.e. the status quo) and what are you hoping they’ll do moving forward?” Then, take a beat to reflect on what you’ve tried already. “Ask yourself, How have you tried to change things, and what was the result?”

Find the parking brakes. It never hurts to try and look at things from another’s perspective. Rather than thinking about what you can do to create change, ask yourself why haven’t things changed already? What are the parking brakes that are stopping people?

28. Use community as a springboard for product development 

Deepica Mutyala, co-founder and CEO of the beauty brand Live Tinted, catapulted herself into the spotlight long before becoming a founder through a viral video she made demonstrating red lipstick as a color corrector for dark circles under her eyes. The video struck a chord, especially with South Asian women who historically felt underrepresented in the beauty industry, and Mutyala immediately built a community beauty page and started creating content catering to this group of people. 

And when the time came for Mutyala to start creating her own beauty product, she had a powerful, loyal base willing to give feedback and provide customer research.  

“Our community was always rooting for us,” she says. They were genuinely excited about our interest in product questions and became our biggest champions,” Mutyala says. “So when we shared the opportunity to test out a potential product, we had no shortage of volunteers.” 

In fact, there were so many volunteers that Mutyala ended up having to curate testing groups through a selection process, in order to make sure she had a diverse group. It was also an intimate process, full of mutual trust. 

“We invited volunteers to come to my house in LA to try out the product, test it, and make sure it worked for them,” Mutyala says. “While we’d post publicly asking our community for help on a project, we were never explicit about what we were building. Everything product-related was all behind the scenes.”

Headshot of Deepica Mutyala
Deepica Mutyala, CEO and co-founder at Live Tinted

29. Understand where brand and performance marketing excel (and where they fall short) 

Between the two of them, Sarah Emmott and Holly Chen have led marketing teams at Atlassian, Google, Square, and Slack, as well as advised dozens of startups on their marketing strategy. And time and time again, they get questions thrown their way about whether companies should invest in brand or performance marketing.

This is a mistake, says the duo. A balanced combination of both brand and performance advertising can create a powerful marketing strategy that not only supercharges brand loyalty but drives immediate conversion. It's not about one being better than the other but recognizing when and how to use them effectively.

Here are a few of the differences between the two approaches:

Table listing the differences in Brand vs. Performance marketing.

To put these ideas into practice, they unpack these two ad examples from Square:

A Square ad that reads "Forged in Flint" on top of a photo of the city of Flint

Square’s Forged in Flint from their “For Every Dream” film series are brand ads showcasing the emotional and inspirational stories of small business owners with no direct product value props. 

A Square ad with a blue background a photo of an iPad with their product that reads "The pocket-size point of sale that powers your whole business"

Meanwhile, Square’s Register performance ad puts the product value prop front-and-center using messaging and imagery optimized for viewers to consider or immediately try the product.

30. Skinny down your MVP

We’ve interviewed hundreds of founders and have heard about all the different ways to approach building an MVP — from launching and iterating rapidly, to focusing on “lovable” features, to not building one at all.

But Kubecost’s Webb Brown moved at a speed that we haven’t quite seen before. “We built an MVP literally over a weekend. It was built using another technology by the name of Grafana, which today is a really big observability platform. It had very little code written but was essentially a dashboard that could show you different Kubernetes cost trends and dimensions,” Brown says.

Along with the MVP, they published a Medium post to explain why they were launching this open-source project. In a matter of days, over 150 people had engaged with the “product.” This was enough of a positive signal for the co-founders to go out and start talking to potential users. “We were focused on answering questions like, what is the problem? Do people care? Are people willing to engage? We didn’t need 120 features to answer those. And sometimes that means being comfortable having a suboptimal solution for the sake of validating a hypothesis in the short term,” he says.

You need to have a clear idea of what you’re trying to prove, at that moment in time, to either de-risk the business or move the ball forward in a material way.

Top illustration by Alejandro Garcia Ibanez, featuring Kalina Bryant, David Hsu, Christina Cacioppo, Daniel Debow, Jiaona Zhang.