Notorious: You Just Have to Care

The best founders, startups, strategies, metrics and community. Every week.

Current subscribers: 9,688, +51 since last week

Share the love: please forward to colleagues and friends! 🙏

Today, we have a special guest blog post from June (YC W21) Co-founder and CEO Enzo Avigo. This is a powerful essay on the importance of having humility and a low ego, building trust and being people and customer obsessed.

You Just Have to Care

Lifetime Customer Value, Customer Acquisition Cost , Net Promoter Score. Time to Market, Net Recurring Revenue, Minimum Viable Product… I feel like I could go on and on regurgitating terms and acronyms like these for hours and hours. Like many of you, I became familiar with these concepts when, nearly 2 decades ago I dropped out of a finance career, to move my first steps as Product Manager in tech.

But today, when I see them across twitter threads or Substack posts, I can’t help but feel a bit dizzy. It’s like for the last 20 years or so, every new software business has been condensed into this sort of dense crossword puzzle.

Why does starting a tech company mean you need to be fluent in this 5,000-word glossary? How did we end up like this? Reflecting on the past decade in the tech world, it feels like the vast majority of entrepreneurs (myself included) have overly indexed on some of these numbers—perhaps losing sight of what truly drives business success. Are all these metrics, definitions, and methodologies truly at the heart of business-making?

I’m sure that some of you reading this post will go like “It’s how we understand how software business works.” And, to be fair, there’s some truth in that. Software companies, unlike more traditional organizations, are different. The unique economics of software, with its zero marginal costs and internet-scale distribution, make them quite a different animal. I get that. But strip back the specifics and the core of entrepreneurship remains the same. Building a business, regardless of industry, market or time, it eventually comes down to one simple thing: making others more successful than they already are. And in doing that effectively, we, in turn, can become more successful.

It’s about lifting others up, helping people succeed in ways they couldn’t alone. That’s the real essence of what we’re all trying to do. Your success as entrepreneurs, eventually comes down to your ability to do this one, and one thing alone.

Looking back at the four years I’ve spent building June, I take a step back and ask myself: what’s the one thing that made June possible? Ironically, our secret never was in the mastery of metrics. I mean it and believe me; as CEO of a data company, you can take my word for it when I say that. What actually allowed us to find product-market fit and thrive in a highly competitive market, was our genuine care for all our customers. 

To a reasonable extent, we treated their problems as our own, which turned out to be more than just good business—it was the foundation of our growth. From day-0 we moved beyond the conventional “company versus customers” dynamic, and completely rejected the “us versus them” mentality. 

By all means, June could have easily been just another statistic, another startup swallowed up by a market dominated by giants. But somehow that didn’t happen. My biggest belief is that it’s in this open commitment to collaboration and empathy the secret that made June the company it is today.

Today’s essay is a broader reflection into how I think about building relationships in general—some considerations on what I see as the essential elements, the implications, and the impact these connections can have on you and your business. I'll also give you a glimpse into how we cultivate these relationships at June and more practical ways for you to apply them to your own business.

Onto the write up.

“Download” your customers’ map

A relationship is essentially a form of connection. An invisible bond that connects two people through mutual understanding. Alice understands Bob; Bob understands Alice.

This connection relies on a common ground, a shared vision, what I like to call a "map." You can think of a map as a figurative representation of someone's desires, goals, aspirations, and motivations, but also their insecurities, their fears and anxieties. It’s a reflection of their inner world.

In every relationship, this map acts like a compass, guiding our interactions. It informs how we phrase questions, how we drive conversations, and more fundamentally, how we behave with the other person. 

With different degrees of accuracy you intuitively have one of these maps for every person that you care about in your life. Your friends, business partner, your family, your colleagues. The deeper your knowledge of them, the more you can feel the richness of the map’s, because you have a better grasp of their driving forces.

As cliché as it may sound, building relationships (even with customers) starts with enriching this map. Understanding what matters to them, what beliefs they hold true, and what they dismiss as false. Knowing what keeps them awake at night and what they consider insignificant. Recognizing how they view your role and your product in their lives and their broader journey as entrepreneurs.

Regardless of the nature of your business or your product, can you answer these questions accurately for your top ten customers? What does this map look like for your most crucial users?

Building these maps is not a task you can automate or capture in a spreadsheet. It's not something that can be revealed through charts or proxied by a metric. You cannot instantly download someone's map, because each map is built on trust and that takes time to develop. It requires careful listening, genuine empathy, and a commitment to understanding another's viewpoint.

A few years ago I came to truly appreciate this idea on a deeper level when casually reading a story about Alexander the Great. I know; what I am about to say might sound overly philosophical, but I’m convinced that great analogies have the power to bring concepts vividly to life in our memories, even decades after we first encounter them. So, here we go anyway..

In 334BC Alexander the Great, led one of the craziest military campaigns in history. 

Starting from Macedonia, this 21-year-old king led a relatively small-sized army across three continents. First, they arrived in Asia Minor, (modern-day Turkey), journeying through Syria, the Levant, Egypt, Mesopotamia, and into the heart of the Persian Empire (present-day Iran and Iraq). 

Then continued into Bactria and Sogdiana regions that now encompass parts of Afghanistan, Tajikistan, Uzbekistan, and Kazakhstan. Eventually reaching Gandhara and Gedrosia, basically modern-day Pakistan and northwest India.

And after 12 long years, he returned back to his native land, Macedonia.

On the surface, Alexander's motives seemed actually pretty straightforward: conquest and imperial expansion. But everything clicked at a deeper level when we came to understand the world as it was known back then.

Might seem like a small detail, but this minor shift in perspective, somehow changed Alexander’s journey entirely. What looked like a quest for power was actually an epic adventure to the very edges of the known world; a pursuit to achieve what no one before had dared.

Holding the perspective of others is hard because we are too entrenched into the image of our own map and it's too tempting to impose this onto others. Using someone else’s map is a simulation act. You need to reproduce their world point of view through your brain. And know how to build up and communicate in a way that feels logical and resonates with them.

Next time someone asks for advice, or feedback, or is looking for an exchange of thoughts, before you speak, pause, reflect, and intentionally think about what they might see, where they might be. What map might they be navigating on? Then help them.

A VIP badge pass

Relationships in business are symbiotic. Alice helps Bob's company thrive, and in return, Bob has more resources to re-engage with Alice. As their collaboration deepens, their profits increase, and they are more likely to work together again. Year after year, both organizations grow healthier, unified by shared goals.

In this dynamic, you no longer view the company merely as a "customer." You start to act almost as an employee of their team. With an accurate map of their needs and goals, you ask insightful questions and propose solutions that align with their objectives, focusing on their real needs. 

Your customers view you not just as a software vendor but as a loyal ally. You're in it together: they share detailed insights into their challenges and successes and you in turn become a trusted partner they can rely on for genuine advice, support, not just sales pitches. On the surface this open line of communication helps you retain them and amplify their success but it also deeply informs your product development.

At June, we consistently see these relationships nurturing a positive feedback loop that enhances the value of our product. It truly feels like we have a backstage pass, giving us access to extremely high-quality feedback. 

Our customers openly share what they love about us and pinpoint areas for improvement. They are open to discuss their challenges with other software and propose ways we could address these gaps. These are the customers that over time evolve into co-builders of your product. They don't just use your services—they help shape them.

This level of access to feedback isn't something that can be bought; it is hard-earned, making it actually a significant competitive advantage that compounds and makes the product significantly better with every cycle.

Caring, it’s everyone’s job

Caring for customers should percolate every level of your team. This should be obvious and it’s a disease that in lots of companies “customer relationships” are solely the domain of roles like “Customer Success” or “Customer Support.” 

True customer relationship building extends beyond titles and departments—it’s a fundamental aspect of everyone’s job within the organization.

Imagine if everyone of your employees viewed customers as integral members of the team. From seeing customers as external entities to considering them as vital as the air you breathe. Your company's fate is intertwined with theirs. If they face challenges, these directly affect your ability to serve and grow with them.

The June Way

Preaching customer obsession, empathy, and connection is common in many companies, yet there's a stark contrast between those who talk the talk and those who walk the walk. 

Over the years, at June, we've demonstrated our commitment to these principles, integrating them into every aspect of our operations. This isn't just rhetoric for us; creating genuine, lasting relationships, it's the foundation of how we operate.

So, here’s a glimpse into how this approach has become part to our way of doing things, and how perhaps you can draw some inspiration.

1) We Use Our Own Software

It might not come as a surprise, but I genuinely believe that the software we're developing at June has been a crucial lever in connecting us with our customers.

Before every customer call, I use June’s Company Profiles to understand how a team is engaging with our product. I look at who is using it most frequently, what features they love, and where they might be encountering difficulties. Seems like a small detail, but this 5min pre-call prep makes the conversation far more effective because I already know the critical points to address.

I find it hard to imagine reading an analytics chart without the granular insights that June provides. The ability to link specific actions to actual users is important at any stage, but it is particularly crucial when navigating product-market fit, where understanding user single user behavior is key to refining the product.

Also, the thought of returning to a time before we had real-time updates on significant user actions via Slack, or when our Sales or Success people lacked access to product data while engaging with customers or potential ones, seems quite unimaginable now.

Like most product analytics platforms, June also works with data. But unlike them, we aren’t interested in numbers per se. We're not in the business of selling your metrics or fancy charts. What's fundamentally important to us is the utility of that data—what it enables you to accomplish.

On the surface, June seems just like a regular product analytic tool, but below the surface June acts more as a Human-Data Interface. Much like the early HCI researchers observed the ways humans interacted with computers and designed technologies that allowed humans to interact with computers in novel ways, at June we’re building software that allows humans to leverage data in better and more convenient ways.

2) Engineers Doing on-call Customer Support

We talked about this multiple times. Having our engineers take care of customer support and success, it’s one of the things that made our team more aware and connected with our customers.

We certainly aren’t the first to have implemented this. All-hands support was a practice well-known before June even existed.

But if anything, we polarized it ensuring that even engineers–arguably the most expensive asset of the company– do that. Every week, we rotate and a different engineer is in charge of fixing reactive bugs, answering conversations in Intercom and making sure each sign up gets the most out of our product.

Because of this as engineers we can better prioritize work that has an impact on our customer’s experience of going from sign up to converting. And every quarter, as a team, we run through our product lifecycle. This helped us identify some of our most impactful work we’ve done.

3) A Shared Chat For Every Customer

At June, we create a dedicated Slack channel for each customer. This channel is open for members from both the customer's and our teams to join. It serves a dual purpose: providing rapid, reactive support when customers encounter bugs or issues with features, and offering proactive support by identifying areas for improvement or important trends to monitor.

Considering how noisy chat clients can be, it’s important to manage comms carefully and ensure that messages are always both necessary and relevant.

That said, I can’t stress enough for us the importance of uniting customers and team members in a single, transparent environment.

4) A Whatsapp Test

Pick up your phone: how many customers can you text right now? Or better saying, how many of your customers have access to your personal phone number?

Since the early days of June, Ferruccio and I have shared our personal phone numbers with our main customers. They know they can have access to the founders any time. This is up to anyone’s self judgment, and it obviously doesn’t mean that they can expect support 24/7, but if anything important arises or they just want to communicate with us through a privileged channel, they can.

Sometimes they text us feature requests, point out small bugs or improvements or give ideas on what we can build to better support them. And because many of our success stories unfold through Whatsapp conversations, we've designed our latest customer story page to capture this experience.

I know this can be a bit of a controversial topic, and I’m not saying you should do what we do, but we made it scale well beyond what we initially thought was possible.

Some final thoughts

In the grand scheme of life, building a business belongs to “hors catégorie”—no questions about it. But there’s a wide gap between building a $100ml/year company and a profitable, well-run, more regular company. Creating a unicorn is like hitting a home-run, and you can consider yourself very lucky if you hit even just one of these throughout your career. But building a software business it’s much more reasonable and way more likely to happen than you probably think.

Perhaps it won’t yield generational wealth and won’t make the headlines of Silicon Valley’s hottest media, but it might very well create car-changing, or house-changing or potentially, even life-changing money for you and your family. And chances are that you can probably do it if you care deeply about the people you are building for.

If you remember one thing from this post, let it be this: people are more than their avatars, username and their emails. They can’t be defined by their roles or the companies they work for. They are not just what they click, what they buy, or how they rate our services. And they cannot be fully captured as promoters or detractors. People are complex, filled with contradictions and unique motivations.

To build genuine relationships, we have to set aside the Silicon Valley archetype of the visionary CEO, but shed ego and embrace humility. Stop pretending like we have all the answers and start listening—truly listening—to what people say and work backwards from there. To “know” is to contextualize and separate. It's about distinguishing between noise and signals, what is valid and what isn’t. It’s about understanding others’ perspectives, constantly refining your perception, and updating the “map” you have of their needs and concerns.

So, with this perspective, keep building. Because building to let them succeed is your ultimate act of listening. And if you care, you win.

Thanks for reading. By way of background, I am an early-stage investor at Wing and a former founder. Please reach out to me on X @zacharydewitt or at zach@wing.vc. Some of the early-stage PLG + AI companies that I have the privilege to work with and learn from are: AirOps, Copy.ai, Deepgram, Hireguide, Slang.ai, Tango and Tome.

Operating Benchmarks (from PLG Startups):

I will continue to update these metrics and add new metrics. Let me know what metrics you want me to add (zach@wing.vc)

Organic Traffic (as % of all website traffic):

• Great: 70%

• Good: 50%

Conversion rate (website → free user):

• Great: 10%

• Good: 5%

Activation rate (free user → activated user):

• Great: 50%

• Good: 30%

Paid conversion rate (free user → paid user):

• Freemium (Self Serve):

  • Great: 7%

  • Good: 4%

• Freemium (Sales Assist):

  • Great: 12%

  • Good: 6%

• Free Trial:

  • Great: 15%

  • Good: 8%

• Reverse Trial:

  • Great: 15%

  • Good: 8%

Enterprise conversion rate (free user → enterprise plan):

• Great: 4%

• Good: 2%

3-month user retention (% of all users still using product after 3 months):

• Great: 30%

• Good: 15%

Conversion from waitlist to free user:

• <1 month on waitlist: ~50%

• >3 months on waitlist: 20%

For more detail on acqusition rates by channel (Organic, SEM, Social etc), please refer to this prior Notorious episode.

Financial Benchmarks (from PLG Public Companies):

Financial data as of previous business day market close.

Best-in-Class Benchmarking:

15 Highest EV/ NTM Revenue Multiples:

15 Biggest Stock Gainers (1 month):

Complete Dataset (click to zoom):

Note: TTM = Trailing Twelve Months; NTM = Next Twelve Months. Rule of 40 = TTM Revenue Growth % + FCF Margin %. GM-Adjusted CAC Payback = Change in Quarterly Revenue / (Gross Margin % * Prior Quarter Sales & Marketing Expense) * 12. Recent IPOs will have temporary “N/A”s as Wall Street Research has to wait to initiate converge.

Recent PLG + AI Financings:

Seed:

• Anon, an early-stage startup that is helping developers add automated authentication in a safe and secure way, has raised $6.5M. Investors include Union Square Ventures and Abstract Ventures, who led the seed and Impatient Ventures and ex/ante, who led the pre-seed.

• Espresso.AI, a startup using AI to automatically optimize code and reduce cloud compute costs, has raised over $11M. The round was led by Daniel Gross and Nat Friedman and FirstMark.

• Log10, a self-improving large language model designed for data management, has raised $7.2M. The round was led by TQ Ventures and Quiet Capital, with participation from Essence Venture Capital.

• Nudge Security, a SF based provider of modern SaaS security and governance, has raised $9.5M at a $40M valuation. The round was funded by Forgepoint Capital and Ballistic Ventures.

• Seam, an end-to-end system that gives people a simple chat interface where they can have a conversation with data in natural language, has raised $6M. The round was led by Bessemer Venture Partners, with participation from Colle Capital, F7 Ventures, Ritual Capital and Umami Capital.

• Stainless, a platform that helps AI companies generate SDKs for their APIs, has raised $3.5M. Sequoia and The General Partnership participated in the round.

Series A:

• Builder.io, a startup using AI to create visual development solutions that optimize workflows, has raised $20M. The round was led by M12.

• DatologyAI, a startup aiming to help researchers better curate AI training datasets, has raised $46M. The round was led by Felicis Ventures, with participation from Radical Ventures, Amplify Partners, M12 and the Amazon Alexa Fund.

• Mimic, a defense platform intended to provide enterprises with detection, deflection, and rapid recovery from ransomware attacks, has raised $27M. The round was led by Ballistic Ventures, with participation from Menlo Ventures, Team8, Wing Venture Capital and Shield Capital.

• Sublime Security, an email security platform designed to write and run custom detection and response rules to block phishing attacks, has raised $20M at a $100M valuation. The round was led by Index Ventures, with participation from Slow Ventures and Decibel Partners.

Series B:

• Augment, an AI-powered coding platform, has launched out of stealth with $252M at a $977M valuation. The round was funded by Index Ventures, Sutter Hill Ventures, Lightspeed Venture Partners, Innovation Endeavors and Meritech Capital.

• LottieFiles, an animation workflow platform intended to create a new realm of possibilities with interactive design, has raised $11M at a $300M valuation. The round was led by M12, Adobe Ventures and Webflow, with participation from Automattic, Square Peg Capital and Figma Ventures.

• Tines, a security workflow automation startup, has raised $50M. The round was co-led by existing investors Accel and Felicis, with Addition, CrowdStrike Falcon Fund and SVCI joining.

Series C:

• Perplexity AI, a startup using AI to build a search engine, has raised $63M at a $1B valuation. Daniel Gross led the round, with participation from NVIDIA, IVP, NEA and others.