Product managers play a crucial role in consumer product companies as they serve as the central point of contact between the company's users, product development teams, cross-functional teams, and leadership team. While a product manager's success is dependent on the impact and quality of their team's work, it's easy to fall into the trap of being a bad PM who contributes little to the team beyond attending meetings and writing a few documents.

However, an exceptional product manager can be a significant force multiplier for the entire organization. During our work at Clubhouse, Harsan coined the term "dangerous product managers" to describe these exceptional individuals.

To become dangerous, product managers must hone their product sense, communication skills, planning/project management processes, and relationship management with their teams, cross-functional partners, and their own well-being. Based on my experience, the most effective product managers exhibit the following traits:

ON PRODUCT SENSE

• Are curious about technology: Dangerous product managers are constantly exploring new apps and technologies, generating new app or feature ideas. They are hobbyists who are passionate about the craft.

• Focus on problems, not solutions: Before jumping into solutions, they ruthlessly identify and drive alignment on stack ranked problems. Once this is done, discussing solutions becomes an order of magnitude easier.

• Weigh all insights to make principled decisions: They know how to consider all the insights of a product (ie, data and user anecdotes) and ultimately use that to make decisions.

• Aim for simplicity: They avoid complexity at all costs and prioritize perfecting a single interaction rather than creating multiple mediocre ones.

ON COMMUNICATION

• Know that less is more: Dangerous product managers don't talk to hear their own voice; they speak to guide and focus discussions. They generally speak for less than a third of the time in group meetings.

• Write structured and impactful documents: They know that docs are often the primary tool used to understand, debate and make decisions. They use short sentences, and incorporate bullet points and tables where necessary. Their documents are typically less than two pages.

• Maintain flexible schedules: They design their calendars with the same care as world class architects, maximizing for negative space and flow rather than positive, or fixed, space. Practically, this means they’re calendar is booked with maker time instead of meetings.

• Avoid status meetings: They share information asynchronously and utilize meeting time for productive discussions, resolving issues, and brainstorming. They encourage others to participate and express their opinions.

ON PLANNING

• Become domain experts: Dangerous product managers don’t need permission to become experts in the problem that they’re trying to solve. Are you building a product for friendship? Go read sociology papers and read books by experts. An AI product? Go learn about the latest model architectures.

• Have strong opinions, weakly held: They have a viewpoint on what should be developed, but never present it as a fact and are open to changing their minds for a better idea.

• Clearly understand their goals: They possess an intuitive understanding of why their goals are important, how to measure them, and what success looks like. All efforts are prioritized relative to these goals.

• Disagree early: They identify potential misalignments early on and seek feedback from relevant stakeholders within and across organizations, and leadership.

ON PROJECT MANAGEMENT

• Don't drop the ball: Dangerous product managers never forget their commitments and always follow up on time. Their team knows that they will always deliver on their promises.

• Drive for accountability: They hold others to the same high standards that they hold for themselves. They push for deadlines and regularly check in on progress. When things slip, they ask why and help their team improve.

• Ensure clear next steps: They never let a meeting end without establishing a clear set of next steps to be taken. They make sure that everyone is on the same page regarding what happens next, regardless of the circumstances.

• Identify and remove bottlenecks: They are constantly on the lookout for bottlenecks in systems and projects and take every possible step to eliminate them once they are identified.

ON RELATIONSHIPS

• Understand the impact of their words: Dangerous product managers avoid using language haphazardly and treat every interaction as if it were on the record. They don't speak ill of coworkers or leadership.

• Earn trust through excellence: They establish trust by being great at their jobs and showing up for their teammates. They don't seek to gain trust by complaining, but instead by demonstrating their skills.

• Proactively build rapport: They identify the most critical stakeholders throughout the organization and develop relationships with them to obtain guidance, advice, and ideas proactively.

• Present themselves authentically: They display all of their idiosyncrasies, embracing their uniqueness with a smile. They are unapologetically themselves and encourage others to do the same.

ON PEOPLE MANAGEMENT

• Create psychological safety: Dangerous product managers make their team feel valued and heard, demonstrating their genuine care every day. They don't just give lip service to this, but actually follow through.

• Follow Radical Candor: They provide direct and actionable feedback to help improve their team's performance, and are not afraid to be candid because they are concerned about how it will be received.

• Give feedback continuously: They don't wait for specific meeting times or reviews to provide feedback. Instead, they offer feedback consistently and in the moment while it's still fresh, often in one-on-one settings.

• Uplevel others with growth mindsets: They scale themselves by making others dangerous by constantly giving opportunities to people that are hungry for them.

ON MANAGING THEIR PSYCHOLOGY

• Avoid hero mode: Dangerous product managers don't view themselves as superheroes, and instead opt for steady, consistent work instead of frenzied and spiky work to avoid burnout.

• Look at the horizon, not their feet: They don't just focus on the current task, but also maintain a broad view of their work and why they are doing it on a personal level.

• Get mad at the problem, not the person: They recognize that people are shaped by their environment, and that typically the intent of those they work with is good.

• Relentlessly disconnect: They understand that taking time away from a problem can often be the best way to solve it by seeing it from a new angle.

Becoming a dangerously good product manager may not be easy, but it is a worthwhile pursuit. It requires sustained effort over an extended period, along with a commitment to continuous learning and a proactive approach to seeking feedback. So why not start your journey toward becoming a dangerous product manager today?

One of the key advantages of NLIs is their accessibility. By allowing users to communicate with a tool or software program using everyday language rather than a specialized syntax or set of commands, NLIs can make these tools more accessible to a wider range of users. This massively lowers the barrier to becoming a power user of otherwise complicated tools, which in turn will create tremendous leverage and creativity for people around the world.

Imagine a world where every software product was as easy to use as Google Assistant or ChatGPT. What kinds of use cases, creativity and innovation will be possible when this is something that can be taken for granted? I predict that one of the first verticals to deeply adopt NLIs will be creator tools such as Figma, Canva, Photoshop and Ableton. Instead of the build and iterate creative process being done with swipes and mouse clicks, what happens when it can be done more similar to if you were working with a professional designer at your side? 

NLIs are not without their challenges. I expect to see dramatic progress in a few of the key problem areas for NLIs within 2023:

• Verticalization: Large Language Models (LLMs) demonstrate powerful generalization power across a wide range of tasks, but are even more powerful when combined with augmentation layers that give domain-specific context. We’ll see a lot more applications of technologies like Dreambooth to help with this. 

• Education: While NLIs will become far more accessible, the onus will be on product designers and developers to create clear onboarding and education about how to use their specific breed of NLI. 

• Speed: Training and deploying NLIs is a very time- and compute-intensive task that requires a lot of specialized time and resources. In 2023 we’ll see a proliferation of developer tools that continue to make deploying generalized LLMs and training your own domain models easier and easier.

Despite these challenges, the potential for NLIs to revolutionize the way we interact with the web and with tools and software is clear. As more and more companies recognize the benefits of using natural language as an interface, it is likely that we will see its continued development and adoption in the coming years. Whether we are using virtual assistants to perform tasks and answer questions, or using NLIs to edit and manipulate images and graphics, it is clear that the future of the web is one where natural language plays a central role.

Traditional conglomerates are, “a combination of multiple business entities operating in entirely different industries under one corporate group, usually involving a parent company and many subsidiaries” (source).

I believe this same model will come to fruition on chain to fund and create niche DAOs that generate on chain revenue streams. This model will be highly useful for music labels, movie studios and other forms of small creator collectives that can produce work that’s monetized through the blockchain.

Architecture

The basic architecture of an On Chain Conglomerate will look like a Hub and Spoke model that’s interconnected through a series of ownership splits managed by NFTs:

• First comes the Hub, which mints ~1000 NFTs and sells ~1/3 to third parties while issuing another 1/3 to operators and retaining the last 1/3 for its treasury.

• Then comes the Spoke, which is created for each business entity or subsidiary. Upon Spoke formation the Hub agrees to a price per NFT which effectively sets a valuation on the original Spoke entity. Then, similar to the Hub, the Spoke mints ~1000 NFTs which are split between third party sales, DAO operators, the DAO treasury and sales to the Hub.

The bearer of these Hub and Spoke NFTs automatically receive a pro rata share of the on chain revenue that flows into their respective treasuries. NFTs for operators can be distributed on some vesting cycle to align short- and long-term incentives for all involved parties.

Benefits

The main benefit of this model is that it creates a standardized protocol for spinning up on chain subsidiaries and creating annuity-bearing NFTs. There could be a single factory method that can encapsulate all of the complexity traditionally associated with creating and funding new businesses.

This model also allows the central Hub to invest upfront capital into various subsidiary business while also letting them operating independently and maintain their own business operations. Presumably, governance does not need to be tied to NFT ownership but instead can be left in the hands of the Spoke DAO operators or the existing token structure they have in place.

Additionally, the On Chain Conglomerate model would allow for new investors to continually buy into the entities on a rolling basis. New generations of NFTs could be created for the Hub and Spoke entities as a new form of fundraising while also offering pro rata rights to existing NFT holders to maintain their stake.

NFT price would be driven by the annuities they create, which would presumably increase over time and drive up secondary sales revenue in tandem.

Limitations

The most obvious limitation of the On Chain Conglomerate model is it doesn’t have a clear answer for working with off chain revenues. Theoretically, a Spoke’s revenue would be passed through some “Oracle, LLC” that was wholly owned by the Hub and would then convert fiat into stable coin which would then be deposited into the respective Spoke. However, this is largely theoretical without clear precedent in the market today.

There would need to be significant thought put into the NFT pricing, both upfront and with future generations of runs to not create unjust dilution for shareholders. Since NFT ownership is directly tied to a recurring annuity, it’ll be important to properly incentivize early buyers through some means of improved economics. It’s also unclear exactly how the SEC would view these annuity NFTs as there aren’t main examples of them in the market today.

Go to Market

On Chain Conglomerates can be started in 4 steps:

1. Stand up the Hub treasury and fundraise around a cohesive vision for the Conglomerate’s future business operations using revenue split bearing NFTs.

2. Find the first Spoke to either buy into or to create from scratch. Presumably, someone could also start with the Spoke and then back in to the fundraising pitch for the Hub. Issue revenue bearing NFTs.

3. Use business operations from first Spoke to subsidize purchase/creation of second Spoke.

4. Repeat, repeat, repeat.

Are you working on or thinking about creating an on chain conglomerate? I’d love to hear from you on Twitter or Farcaster!

Design: One size does not fit all

Design is a highly diverse discipline, with dozens of different fields and specialties. Similar to software product development, the scope and scale of design teams is highly variant and meant to reflect the needs of their organization. For early stage startups — those that are pre product-market fit, or have early market traction — the design needs tend to follow a similar pattern, and then tends to vary based on the specific business model of strong product market fit companies.

The 3 most important types of design for early-stage companies

At the highest level, founders of early stage companies should focus on:

1. Product design

2. Web design

3. Brand design

Here’s a breakdown of what each of these types of design means:

• Product design is the user experience for your service or product. This doesn’t just include software that you build yourself, but also includes every other touchpoint you have with your customers or prospects. Product design isn’t just about creating user interfaces, but also developing wireframes, user research, and user experience testing.

• Web design is a company’s front door to the world. In 2020, your website is the most basic currency of reputation for every company, and needs to make it clear what you do and what people should care. For most companies, a website is step 0 for starting to get customers.

• Brand design is the why behind your company’s what. It’s how you explain who you are to people, by codifying the way you represent yourself across every surface. As Paul Rand says, it’s “what people say about you when you’re not in the room.” This isn’t just your logo, fonts, colors, aesthetic and tone, but also the slide decks, emails, ads, and one pagers that you put out into the world.

What kind of design should my early-stage company focus on?

How much effort should companies apply to each of these three types of design? It of course depends, but there are some easy rules-of-thumb you can follow:

• Pre-product-market fit companies should focus almost entirely on product design — with less effort on web design and brand design. This means spending as much time as you possibly can working on your product, and then bookmarking a few hours each week to make copy edits to your website. Don’t focus too much on the visuals at this stage, but rather your messaging and information architecture.

• Early-market-traction companies should maintain focus on product design, but start to ramp up web and brand design. These companies should do spike projects to develop more website content and begin developing their first marketing channel(s) and content roadmap(s) to activate their audience.

• Strong-product-market-fit companies should focus across the board. Spend time clarifying your brand identity, and take the time to review your entire user experience. Then, up the ante on production across all channels by turning brand design into a service center that can be consumed by your cross-functional orgs (ie, marketing and sales).

I don’t have a designer on my team. What should I do?

It depends on the current phase your company is in:

• Pre-product-market fit companies should focus on talking to customers. You should be spending most of your time talking to users to understand their problems. All of the tools listed above are approachable, even if you’ve never “done design” before. You can read Don’t Make Me Think, Design of Everyday Things, Just Enough Research and watch Gary Tan’s YouTube lectures as good primers on the subject if you’re interested.

• Early-market-traction companies should consider hiring contractors to help with web and brand design. At this stage, it’d be hard to justify staffing for product design unless the founding team still maintained all user research, and just needed support with UI/UX. It might also make sense to staff web design if you have proof it’s a really useful channel for you today.

• Strong-product-market-fit companies should start hiring staff designers. Think of the trade-offs for hiring full-time versus working with outside support. Think of how you’d invest into these three areas of design, and what the top goals would be from anyone you worked with to get help. Then, start staffing by hiring full-time design, freelancers, and/or working with an agency.

How do I get started?

If you’re new to design, here are a few concrete actions and tools we recommend:

• User research: The Aesthetic team recommends scheduling 2–3 user research interviews each week, ideally at the end of the week so you can also do usability testing on new features from the week.

• Take notes and record sessions: Make sure the entire team’s in each interview and take notes, record the sessions and do an affinity mapping exercise to formalize your learnings. We recommend Fullstory for recording app and website user sessions.

• Design your website: Aesthetic loves Webflow for this phase, not just because they’ve built an awesome product and great people, but also because they’re YC alum and former batchmates :)

• Iterate on your brand design: Aesthetic uses Figma for all of our marketing template designs, and the Adobe suite for developing our (vector based) brand identities. Depending on the specific tech stack, there’s a wide variety of solutions for helping deploy design systems to enable reusability and consistency across your product teams. Figma’s collaboration and animation support is second to none.

With a limited amount of time and an expanding number of ways to reach an audience, how do content marketers make ends meet to not find ourselves burnt out, lacking inspiration and creatively blocked? When you have 10 different social networks at your disposal and each requires a different flavor of content, how do you make the most of your investment into content creation to maximize the return on your investment?

Enter content repurposing.

What is content repurposing

Content repurposing is a method of remixing or recycling existing content into a new format or package to maximize the value from the initial work. In its simplest form, content repurposing can be reposting an old piece of content to drive more engagement with it after it was created. In its more advanced form, content repurposing is creating new, derivative work based on the original content that was created.

You can think of content repurposing as content alchemy. How might you intake one piece of content and turn it into one or many different types of content in various formats? This process can be done manually by hand, or using various software products on the market today.

Why is content repurposing important

Content has been, and always will be, king. There’s no question that the human appetite for content is insatiable. Marketers are well aware of this, and have been doubling down on their investment into content creation for the last decade.

According to a 2017 HubSpot report, companies spend 46% of their marketing budget on content creation. Because companies are spending more time and money on content creation, the quality bar has also gotten higher: blog posts have gotten 50%+ longer and take 60%+ more time to write. It’s no surprise that it’s now common practice for marketers to reuse their existing content to increase its ROI.

How to repurpose your content

There’s a new wave of tools that are now available to make content repurposing a seamless and easy process. Whether it’s a tool like Headliner which turns podcasts into video clips, Designrr which turns blog posts into eBooks or Aesthetic which turns websites into images, we’re entering a golden age of new, generative tooling that can ingest content in one form and generate variations of it in another formats.

Content repurposing is a trend that we believe is only just beginning and could represent one of the most important shifts in the marketing landscape for the next decade. If investment into content creation can have increased returns, companies will have higher conviction to invest even more into content creation, thereby adding another revolution to the flywheel.

Why Stories Won the Internet

The way companies with an ads-based business model make more money is relatively straightforward: get users to spend more time consuming relevant content and seeing more ads. For over a decade, consumer internet companies have been tweaking and improving upon the traditional feed-based content consumption model. First there was Google’s paginated results, followed by Facebook’s infinite scroll and Pinterest’s masonry grid. Each is designed to balance exploiting what the app already knows about its users with exploration of new topics adjacent to the user’s current preferences.

Stories were the first new discovery paradigm that completely changed the way social apps began to think about engaging with their users. Beyond just how users consume content, Stories also changed the way people thought about creating content. By making Stories temporal, the quality bar was lowered so users don’t have to overthink whether something they share should be a part of their permanent record on the internet. Suddenly, users weren’t worried about polluting their own self image (or their friends’ feeds) which made it a lot easier to create content at a much higher volume than they did with feed posts.

From a metrics perspective, it makes sense why this new paradigm is so attractive: Stories users end up spending more time in-app across more frequent sessions and end up direct messaging each other more, creating a virtuous feedback loop of engagement. In early 2019 Instagram reported that they had 500 Million daily active users of Stories, with 1 Billion monthly active users of the app overall! That DAU-to-MAU ratio is astounding, and something that’s understandably envious to the rest of the consumer app ecosystem.

Why Stories are Hard for Marketers

While the cat’s out of the bag that Stories are the winning format for mobile, marketers are left scratching their heads about how to handle supporting all of these new native formats. Depending on a marketer’s type of business and target audience, they now has to deal with Instagram (Grid, Stories, Reels, IGTV), Snapchat, TikTok, Google (SEO, AMP Stories), Pinterest (Pins, Stories), Facebook (Posts, Stories), Twitter (Tweets, Fleets) and LinkedIn (Posts, Stories).

The proliferation of at-scale social networks presents a massive opportunity for marketers to reach their audience unlike ever before, but it comes with a very real cost. Each channel has its own rules, best practices and creative sizes which means a “one size fits all” approach just simply doesn’t work. Practically speaking this means that if a marketer wants to cross-promote a blog post across social networks today, they have to produce 4+ creative formats and publish it to 5+ channels. This leads to a meaningful decrease in velocity and increase in the time between publishing a blog post and actually being able to promote it. When combined with the fact that all of this hard work goes away after 24 hours, it’s clear that this is a very real challenge today.

Almost overnight, the bottleneck for marketers has become creating all of the design assets they need to maximize their reach and maintain their quality bar. Companies like the New York Times have dedicated 20+ person design teams just focused on solving this problem, but for the average company this isn’t even a distant possibility. More likely, the marketer has a shared design resource with other parts of the company, and is relegated to jump into design tools themselves to try and make ends meet.

What Happens Next

Stories are the straw that broke the marketer’s back, and with their recent widespread adoption will come a new wave of products that are meant to make the process of generating stories and other social content dramatically easier. Today marketers have 3 choices for producing stories: native creation tools, templated design tools, or pro design tools.

We’re at the beginning of a new era of design tooling that generates beautiful, on-brand social content automatically. This fourth type of tool will let marketers remix their existing content into all of the relevant formats to power their social strategies. These tools won’t automate the role of the designer or marketer, but instead elevate their position from being the executor to the strategist.

With social media’s rise, we’re now in round 2 of the, “web is dead” argument. There’s a whole new generation of internet users for whom the internet is their social media apps. In the same way that baby boomers viewed the browser as the internet, to Gen Z social media is the internet. This isn’t a surprise when looking at recent time spent metrics, but a less obvious and perhaps more consequential shift is happening underneath it all: content creation.

Today’s content is siloed from the web

We estimate that content creation is happening today at roughly 100x the velocity in social media’s walled gardens as it is on the web at large. While there are still 100,000+ websites being created each week, there are 100,000,000+ social posts being created across the likes of Instagram, Tiktok and Snapchat. The vast majority of this social content is both temporal (it goes away) and opaque to the rest of the web at large. Social media content is invisible to the web, and is growing far faster. This presents a big risk to the web.

A core tenet of the open internet is that content can be accessed by any device with a network connection. As developers are well aware, there are protocols and open standards in place that ensure the web stays accessible, and there are massive communities of people whose entire focus is making sure that this vision stays true. However, social media sidesteps all of this and creates its own private ecosystem of content that is only accessible by using a closed protocol (ie, Instagram’s app). This gives them massive control and influence over how and what people discover, and it also means that the open web has a massive hole in it.

The implication for content creators

As a content creator today, it’s more important than ever to decide where your allegiances live. What is your primary content creation mechanism, and what channels do you use to distribute it? How does the channel influence the content that you create, and which audience is the most valuable to you and your stakeholders?

The biggest issue with this new flavor of the web is that the content creators don’t actually own the content they create. Whereas in the open web people host their own content that’s discovered through aggregators like Google, now the content hosting and discovery are bundled together. This means that creators are even more beholden to these platforms and are at risk of having their audience taken away from them. We’ve all read horror stories about creators who spent years building an audience, only to have their engagement drop overnight because a platform changed their ranking algorithm to prioritize a new type of content.

Content creators are more empowered than ever to produce content that reaches their audience, but with this change they are also more captive to the platforms that feed them. This is true for anyone that participates in the social media circus, whether as an individual consumer, creator or a business.

What does the future hold?

If the last decade has been a bundling of content creation and distribution, the next decade will be a disaggregation of these two equally important functions. Instead of creators creating content directly within a distribution platform, they will create and host it independently and then syndicate it through their platforms of choice.

Social media companies are already creating new ways to incentivize content creators to publish on their platform, like what we’ve seen from TikTok and now Snapchat. These incentive structures are attractive at first glance, but also don’t prevent creators from porting their content elsewhere. What will be the open web equivalent of Instagram Stories or TikTok? Google has an opinion on this with AMP Stories, but unfortunately these just end up being, “yet another” thing for creators to think about with no clear payoff outside of large media companies today.

In the future every creator will have their own content management system that publishes to the web at large, and cross-posts variants of that content to their distribution channels of choice. This has already happened with websites, but will continue to grow in use for other formats as well. CMS can be used for many things beyond websites, like plugging into gaming engines or auto-generating social media assets. Content authoring and content distribution are two sides of the same coin, but don’t have to be coupled.

I believe that in the near term, a higher percentage of the content on social media will be ported from the open web, and used as a bridge to connect creators’ ideas into all of the places that their audiences spend time.

For those among you who are preparing for your interviews over the next few days, I wanted to share some of the best practices that helped Andrew, Nate, James and me pass our interview and earn URX’s place in the Summer 2013 batch.

Quick, concise answers are key

Each interview lasts about 10 minutes and the interviewers’ goal is to get as much signal about the team as possible. Because of this, the interviews are structured as a series of rapid fire questions that will cover a lot of ground. Having well prepared, concise answers that you can recall quickly is probably the single strongest indicator of success for your interview. We prepared for this by coming up with a list of ~50 expected questions, each with their own with 2–3 bullet point response. Then, we spent hours grilling each other and loaded them into a flashcard webapp for self testing. This took some time, but was well worth it.

Know your 5 points, and make sure you speak to them

In any interview, it’s crucial that your personal narrative shines through. Unfortunately, the rapid fire nature of YC interviews makes this difficult. In your prep, it’s crucial that you identify the 3-5 most important points about your business/team that you need the YC interviewers to hear. These can be things about your backgrounds, user growth, revenue, or the like, and together should tell the best version of your story. For our team, these were: 1. We’ve known each other for a long time, and have lots of experience in the space. 2. We’ve already built the first version of our product 3. We already have customers 4. We know what we want to get out of YC

We entered our interview with these points ingrained into our heads, and it was my personal mission to make sure we hit on each of them. Sometimes, this was straightforward because the interviewer would ask a related question. Other times, this was more difficult but overall really helped us guide the conversation in the way we wanted it to go.

Each panel’s style is different, but be ready to get grilled

Our interview panel consisted of Sam Altman, Geoff Ralston and Garry Tan. From the moment we walked in the room (before we even sat down!) we started getting grilled. I’ve heard some people describe the interviews as being a bit of a “stress test” seeing how you deal with highly intense situations. Each interview panel is different, and you should expect the style of the interview to be tailored to the people delivering it. Some are more “lean in”, while others are a bit more passive. The substance of the interviews is the same, so if you’re really prepared it shouldn’t matter too much who interviews you.

Be a master of your own domain

The YC partners are one of the most intelligent, experienced groups of people I’ve ever had the chance of working with. Generally speaking, no matter what domain you’re in, one of the YC partners will know at least as much — if not more — about it than you. As such, it’s crucial that you aren’t just a master of your own product, but the industry around it. This isn’t just true for your YC interview, but is important for your company’s overall success. Unfortunately, this isn’t something that you can “cram for” in a few day window, so if you’re green to your industry make sure you have a good story to tell.

Make sure everyone speaks

Y Combinator emphasizes the strength of the founding team above most other things. As such, it’s crucial that each member of the team is equally prepared for the interviews. Everyone should have the chance to speak and should maintain the same level of polish. For us, we decided ahead of time who on the team would answer which sorts of questions, and agreed that I would answer any questions where it wasn’t clear who else should talk. Generally speaking, there will be one person that answers most of the time, but it’s important no one tries to, “run away with the show.” Teamwork in the interview is as important as it is in the office.

Have a demo, but don’t expect to show it

I’ve heard many people debate whether the interviews should include a demo or not. The general convention is that the partners are more interested in hearing people talk about the thing, as opposed to seeing the thing itself. That said, there seems to be no consistency as to whether a team actually gets to show a demo. In our case, we were introducing a new concept that was too abstract for most people to understand so we had a <30 second demo in place to make it clear exactly what we were talking about. We were able to show it, but only after trying about 3–4 times :). So, don’t rely on your demo as a crutch to tell your story.

The YC interview process is as challenging as it is invigorating, and I hope these 6 tips help you in your journey. Questions/feedback? Find me on Twitter @jmilinovich

Going into 2020 I was familiar with Jeff Bezos' Type 1 / Type 2 decision making framework, but I was less sure about how to apply it in practice. It's easy enough to reflect on whether a decision seems reversible, but it's deceptively difficult to truly know the implications of a decision before you make it.

In my experience running Aesthetic and advising founders, I've learned that it's a common mistake to overestimate the first-order reversibility of a decision while under-estimating its second-order effect on a company’s strategy. Decisions about company strategy should be made slowly and deliberately, whereas decisions about tactics should be made quickly. But, how do you really know whether a decision is just about tactics, or has far-reaching implications about strategy?

A case study in flawed second-order decision making

A friend of mine ("Elliot") was running a VC backed tech-enabled architecture firm, whose vision was to reinvent the architecture studio model by automating a lot of the manual work done within architecture firms using software instead of using humans. They believed that much of the non-specialized work (ie, billing, project management) could be completely automated, and that some of the specialized design work (ie, developing CAD plans, interfacing with construction) could also be automated.

Their founding team was a combination of an accredited architect, a senior software engineer, and a real estate sales industry veteran. Within the first few months their sales founder had lined up commitments for 4 housing projects that wanted to be built using their fledgling startup. They called a team meeting to discuss their plan for delivering upon this lofty scope of work. These 4 housing projects would represent spectacular growth for a company at their stage, which they felt would be great proof of their approach to VCs to help them raise more funding in the future.

The issue, however, was that they didn't have the ability to deliver upon these 4 projects using the resources that they had on the team at the time, and their software wasn't at a point yet where it was truly able to lessen the workload. They would either have to turn down some of the clients, or hire new employees to help service the work.

They felt like turning down a client was an irreversible decision that they would regret, whereas hiring someone to do the work was reversible since they could fire the person if they really needed to do so. They decided to hire the person to fulfill the work. What they didn't realize or anticipate was they had actually made an unintended second-order decision about their growth strategy which set a dangerous precedent for them in future decisions. Fast forward 2 years and they've hired 25 more people to help scale their architecture services and have yet to actually build any software to automate anything. They had accidentally become a "normal" architecture firm, instead of fulfilling their vision of automating manual work using software.

What is early stage startup strategy?

What Elliot's company was missing was a clear strategy to guide their decision making. Because they were lacking a clear strategy, their day-to-day decision making ended up becoming out of alignment with their vision. By the time they realized this, it was too late.

I subscribe to Michael Porter's definition of strategy as the approach a company takes to, "achieve a sustainable competitive advantage by preserving what is distinctive about a company." For a software company, strategy applies at the macro level ("how do we invest our resources?") as well as the micro level ("what user experience do we foster with our product?") and everything in between ("how do we price, position and package our product?").

A cohesive strategy defines the "why" behind the day-to-day execution of a company, and acts as a scaffolding that's self consistent at all layers of abstraction. For a startup company, the strategy is what bridges the gap between a company's vision and their tactics in pursuit of their mission.

Most strategy frameworks and exercises are too heavy for early stage companies. By the time the strategy is defined, the company has learned enough from being in market that it's time to change it all over again! Instead, early stage companies should simply define their mission statement (what impact do we make on the world if we succeed massively) and their vision statement (their hypothesis on what they're going to build in the next 2-3 years to make progress towards their mission). Then, they should go through a light product strategy exercise that helps codify how they plan to go about validating/invalidating their vision. Gibson Biddle's product strategy exercise is the best approach in my experience, and can be done with half a day of team collaboration.

How to avoid flawed decision making

Once a company has defined their mission, vision, and product strategy they should decide on what time horizon they will revisit this using new information. Generally speaking a company's mission statement will stay the same but its vision and product strategy will change periodically. As a company matures, its vision will become more locked in but its product strategy will still change at least annually.

After the strategy is locked in, it should be treated as the north star for any decision making until it's revisited. Any time that a team member is making a decision—big or small—they should be able to rationalize how it ties up to the product strategy. Any company a project takes on should be clearly tied back to the product strategy pillar that it supports, and the team should be able to unanimously agree about this.

When team members are deliberating about a decision, they should be able to challenge each other at the level of the company strategy. If this isn't happening it means that the strategy is either not cohesive enough or not communicated clearly enough across the team.

If a team is able to foster this level of clarity and communication about their decision making, they'll increase their chances at accidentally making irreversible decisions about their company strategy. If a company is able to do this successfully, their decisions will compound over time to help them prove (or disprove!) their articulation of their vision in service of their mission.

In short- my biggest learning about product strategy from URX is the importance of aligning your vision with your business model. As with so many things in life, there’s a big difference between understanding things with your head, and knowing them with your heart. I think this is especially true for the “resilient founder” persona who has the fortitude to endure the endless sea of challenges that plague early stage startups.

To call the URX journey anything other than magnificent would be an understatement. I learned more than I could have ever imagined from that 3.5 year period — from raising capital to hiring executives, managing managers of managers to setting the right goals — I am simply not the same person as I was before URX. There are many great resources for founders that outline how to not fail, and what to do when it’s time to sell, so instead of rehashing what’s already been said I want to share my most unintuitive lesson learned from operating URX so that you don’t have to learn it the hard way.

The Evolution of URX’s Business Model

URX was one of the first mobile deep linking companies. For the uninitiated, deep linking helps create links into apps so that they can work in a similar way to the web. Without deep links, apps can only be opened to the “top” of the app, which means that the foundation of the internet — hyperlinks — can’t work for apps. This created countless broken experiences for users (how many times have you clicked on a link in an email that took you to the mobile web instead of an app?), and we believed that this was a big opportunity for a startup to solve. We believed that if you could be the company that helps apps succeed with deep linking you could build a comprehensive (and proprietary) understanding of the content inside apps, which would let you create a new paradigm for contextual mobile discovery. We firmly believed that mobile devices would be better if they understood your context and could help you seamlessly navigate across apps based on your intent.

To realize this vision, the first product we built was an SDK and click server that would help an app developer get started using deep links. Developers quickly started adopting this service, but it wasn’t clear this was something they’d be willing to pay for. In talking to our users, we learned that a major use case for deep linking was mobile ad retargeting. The only type of mobile advertising available at the time was “cost per install” based advertising, but with deep links you could actually start running re-engagement campaigns, and retarget your users across apps to bring them back into your app. To validate this insight we started pitching a mobile retargeting solution, and it turns out people wanted this: by YC Demo Day, we had AirBnB, LivingSocial, SideCar and HotelTonight as clients. We raised a $3.1M seed round, and were on our way.

Over the next 6 months we continued to scale our mobile retargeting business, and raised a $12M Series A to continue expanding our team and our ads business. We capitalized on the press to launch the second version of our free deep linking product OmniLinks to help accelerate developer adoption of our platform. The team was happy, and we were motivated with this new influx of capital to continue working on our mission. However, about 2 months later we started to hit some serious scaling bottlenecks. We were running our ads through third party aggregators (SSPs like MoPub, OpenX and Smaato), which meant that there was no quality controls (our top inventory sources were the Chive and Grindr) and we couldn’t understand a user’s context when seeing an ad. Because of this, we weren’t able to fulfill our advertisers’ budgets or hit their goals at scale. To solve this problem and begin fulfilling our mission of contextual mobile discovery, we believed we would have to become an ad network and go start selling publishers in addition to advertisers. So, that’s what we did. We spent the next 4 months building our contextual ad serving stack, signed up our first publishers up and officially launched AppViews with a host of great mobile publishers.

In retrospect, by becoming an ad network we misaligned our business model with our vision of contextual app discovery. When you’re operating a media business, your success metrics are very different from a discovery/search company. Instead of being purely “user first”, we had to delicately balance the needs of end-users with those of publishers and advertisers, which were very frequently not the same. We had set very real expectations with our customers and board that we would continue to aggressively grow revenue, which forced us to make decisions that were not inline with our mission. This caused a few important moments where we had to make product decisions that felt inauthentic towards our vision, but were required to execute on our business model. By the time we had realized that we chose the wrong business model to support our mission, it was too late for us to change it. Whether we liked it or not, we had customers relying on our product, and set our revenue goals around scaling our media business.

How to tell if your business model and mission are misaligned

The best way to make sure your business stays inline with your mission is by making sure your mission statement fully encapsulates the value you want to deliver to your customers, not just the product/technology you want to build. If you get this wrong, you might not end up building the business you want to build.

To tell if your business model and mission are misaligned, go through the exercise of asking yourself these questions regularly:

To achieve our mission:

1. What are the various products or technologies that we could build?

2. Who is the primary benefactor of this product(s)?

3. What is the most ideal way we would make money?

If we’re successful in executing our current business plan:

1. What is the specific pain point we solve for our customers?

2. What is the impact our company has on the world?

3. What is our strategic differentiator within the market?

If we’re successful in achieving our mission:

1. What is the specific pain point we solve for our customers?

2. What is the impact our company has on the world?

3. What is our strategic differentiator within the market?

The goal of asking these questions is to identify the gaps/misalignments between the near- and long-term viewpoints on your business. No company has ever been able to constantly pivot its value prop to create its strategic differentiator. The most successful tech companies of all time have been able to expand upon the same customer pain point and value prop through the duration of their business:

• Google still helps people search for answers to their questions

• AirBnB still helps people make supplemental income by renting their houses

• Pinterest still helps people discover and do things they love

• Netflix still helps people watch movies in their homes

In order to create lasting value for your business and your customers, you have to make sure that your near- and long-term goals are inline with each other. This is a difficult balance to maintain, but is arguably one of the most important things you can do to ensure your company’s success.

What to do if you’re misaligned

In answering these questions if you identify a misalignment between your business model and your mission, it’s time for you make some decisions. Ultimately- do you change your business model, or do you change your mission? There’s no universally correct answer here, as this is largely stage dependent.

Changing your business model

• If you have an established business, changing your business model creates serious customer risk and is probably not the right idea. In this case, you should evaluate changing your mission to better reflect your current business model.

• If you have a nascent business, changing your business model is something you can validate by talking to your existing/prospective customers. How is each business model perceived by your customers? Is one more preferable than the other?

Changing your mission statement

• If you have an established business, what would the impact be to your team if you change your mission statement? If you’re a mission driven culture, do you risk attrition if you change your mission? Talk to your executive team to get their feedback on this.

• If you have a nascent business, your mission statement should be considered a “work in progress” that is likely to change as you learn more about your customers.

Maintaining state between the near- and long-term identify of your business is one of the most difficult jobs of any founder. You only have one chance at a first impression, and getting this right will help create a cohesive story for your company to employees, recruits, customers and investors. If you get this wrong, you will find yourself in a constant identify crisis, which will consistently cause confusion and may never be able to be corrected.

Disruptive technologies create transformative business models when they enable a 10x better consumer experience (ie, Netflix with streaming tech vs. going to Blockbuster) or a 10x cheaper back office (ie, Instacart with mobile tech vs operating a grocery store).

Today, the blockchain is arguably a 10x+ worse consumer experience for anyone that hasn’t already been red pilled, but it can be 10x+ better in cases that rely on incentive alignment between large groups of people who don’t know or trust each other. This is the crypto mullet’s opportunity: web2 consumer products upfront, combined web3 technologies in the back.

Crypto mullet’s customers don’t think about wallets, tokens or crypto. Instead, they log in with their email addresses, pay with their credit cards and access the company’s services through a normal web browser/app. Crypto mullet’s back offices, however, are decentralized and governed using thoughtful tokenomics and encoded via smart contract. They weave together NFTs and FTs to align incentives through through profit sharing, shared upside, governance, etc.

Braintrust, VectorDAO and MetaFactory are great examples of the crypto mullet model in action. Braintrust is disrupting the talent agency model by combining a Toptal inspired consumer product experience with a service DAO on the back end, and Vector DAO is doing something similar but for the design agency market. Instead of building C Corps with 10,000s of staff, these companies are managing their supply chain via a DAO. MetaFactory is a decentralized clothing brand whose apparel is designed by the community and whose creators and buyers get ownership (ie, tokens) in the DAO to help drive future decisions.

Generally speaking, I think there are two types of business model that are most likely to be disrupted by crypto mullets:

1. Service businesses, movie studios, music labels and news networks that employ 10,000s of people doing specialized, project-based work within teams.

2. Fashion, CPG, and marketplace businesses that rely on supply chains or networks of many vendors, manufacturers or sellers for the products they product/sell.

Like startups, crypto mullets must start by focusing on a single, underserved market segment and then expanding into others over time. This is critical so these companies can stay small and off-the-radar to start with before needing to compete head-to-head with existing incumbents.

For example, a crypto mullet disrupting CPG could start with a wine of the month club, or a movie studio could start out by creating clever video ads for a small brands. Similar to any startup, a crypto mullet’s core advantage is its speed, so picking the right first small market is critical so they can stay focused and move quickly.

What are some of your favorite examples of crypto mullets in the wild? Share them with me on Twitter!

At least 2 of the top 10 projects on OpenSea will be powered by on-chain SVGs.

Most NFTs’ image assets live off-chain using something like IPFS. While this makes sense in many cases where the assets remain static, these projects are only using a fraction of the potential enabled by the blockchain.

In 2021 we’ve seen a few projects emerge where the image files are actually encoded into the smart contracts using SVGs (ie, Nouns DAO, Blockheads, ChainRunners) which enables a whole new level of functionality and composability. I believe this is going to be a critical part of NFT infrastructure moving forward, and 2 of these projects will break into the OpenSea Top 10.

2 large (50M+ DAU) social networks will launch token-gated functionality.

Discord is the de facto home for NFT communities today because it lets a dedicated group of fans interact with each other around a niche topic. However, there’s so much left to be desired in order to enable authentic community building on the web.

In 2021 some forward-thinking startups (ie, CollabLand, Aesthetic) brought token-gated functionality to the world and in 2022 I believe we’ll see mass-scale adoption of token-gated access to communities across the internet.

2 large ($1b+ valuation) web 2 companies will launch web3 business models.

Today we separate the world into “web2” and “web3”, but in reality things aren’t that simple. Whereas all early web3 startups are new companies that build native to this new technology, we’ll going to seem many hybrid “web2.5” companies in 2022.

In particular, I think 1 creator platform (ie, Substack, Patreon) and 1 real estate company (ie Opendoor, Compass) will launch crypto native functionality where they either bring a large part of their existing business on-chain or create a new on-chain business line.

Olympus DAO will reach 500,000 holders, signaling that DeFi 2.0 has entered its next phase of adoption.

Olympus DAO is a partially collateralized, floating price currency that aims to be the de facto reserve currency for all crypto projects in the future. When it was released in April ‘21 it introduced many new DeFi primitives to the world and is credited with creating, “DeFi 2.0”.

There are currently ~100,000 “OHMies” who are currently holding and staking OHM—referred to as (3,3)—and I believe that the number of OHMies will quintuple in 2022.

A web3 competitor to Wikipedia will emerge.

Wikipedia remains one of the best examples in the world of internet-scale collaboration. Roughly 100,000 people are active contributors to Wikipedia today, with no clear incentive to do so other than to feel a part of something bigger than themselves.

In 2022 a new, real threat to Wikipedia will emerge that combines modern web2 technology with a web3 incentive structure. I believe Golden is best positioned to do this but think there’s also room for a new incumbent to go to market and gain traction here quickly.

In URX’s first 2 years, we grew from 4 co-founders to a 20-person engineering, product and business team. With this growth, many of our internal processes and communication channels broke. It didn’t feel like we were moving as fast as we were before, and it took longer to get everyone on the same page.

How can we grow startups as efficiently as living organisms?

After analyzing our current processes, I came up with a new set of tenets that guide how I operate as a CEO. Thanks to the way communication overhead scales exponentially as a team grows, I expect to have to revisit these continuously along our growth curve.

Here are the 7 lessons I learned growing URX from 4 to 20 people.

Lesson 1: Learn to delegate.

Learn the difference between things that are important enough for someone to do, and things that you should do. As a founding CEO in a growing company, your job changes continuously and success is determined in part by how quickly one can delegate responsibilities to others.

Generally speaking, as soon as you’d consider yourself, “good at something” you should hire someone to do it, or have someone else on the team own it. It’s important to keep your time free to find the, “unknown unknowns.”

Ben Horowitz talks more about this in Do You Feel Pressure Or Do You Apply Pressure.

Lesson 2: Stay highly leveraged.

As a CEO, it is your responsibility to balance enabling your team to stay focused on execution while still having time to triage the most important issues in your business. It requires a high degree of discipline making sure that your time is always well spent.

For me, I gained a lot of leverage when I learned to say no. Whether it be internal meetings, “coffee invites”, or decisions you think others should make- learn to say no.

Jessica Stillman talks more about this in Why You Need to Stop Being So Nice.

Lesson 3: Own your schedule.

It’s well known that time is everyone’s most limited resource. This is even more true as a startup CEO, as there is never any shortage of things that, “could” be done. It’s crucial that you clearly define your priorities and reflect that in how you spend your time.

For me, a part of this was doubling down on becoming an email machine. I pride myself on being an email expert that is able to process 100's of emails per day using a combination of filters, rules, and reminders. My calendar’s been referred to as the, “Mona Lisa” of calendars — ok, maybe that’s just what I call it — and I’ve really taken pride in my productivity. I’ve developed my own “stack” that includes products like SaneLater, ClaraLabs and Boomerang.

David Allen talks more about this in Getting Things Done.

Lesson 4: Manage your emotions.

As a founding CEO, your emotions are amplified throughout the organization. Everyone looks to the founders to know whether things are going well or not. The worst thing that could happen is you spook the team because you’re having a bad day. Whether you like it or not, you are the barometer for the company’s anxiety level.

The hardest part of building a startup is how quickly things change. It’s an emotional rollercoaster, and if not managed well will get the best of you. For me, this involves trying to live an integrated life that also leaves time for loved ones, working out, writing, sleeping and friends.

Ben Horowitz talks more about this in Managing Your Own Psychology.

Lesson 5: Repeat yourself.

As a team grows, it becomes increasingly difficult to keep everyone on the same page. Make a point to repeat yourself and hammer home the company’s goals and vision through well-defined communication channels. Invest into well-maintained internal documentation- you can never have “too good” of an internal knowledge base.

At URX, I send a Monday email to start the week, and we do an all-team retro on Fridays where we talk through our goals, successes, launches, announcements, and wins for the week. We’ve built this into a part of our culture, and our Weekly Retro is a highlight of the week.

Peter Drucker talks more about this in The Effective Executive.

Lesson 6: Align your vision with your goals.

Make your company’s vision tangible by connecting it to actionable goals. In parallel, gut check that every goal is on the right scalars and vectors to help you properly measure success against your mission. Be careful not to overly optimize for either the near- or long-term.

At URX, we’re building a very complex technology, and I’ve learned first-hand the importance of having a clearly defined vision that the team can rally around. A well-defined mission statement is the only way a leadership team can build a cohesive plan that is aligned across the company. This plan can be used to then define your team’s goals, priorities and hiring needs.

Jim Collins talks more about this in The Hedgehog Concept.

Lesson 7: Know your precedents.

The beauty of the software industry is that it is built on the shoulders of giants. Whether we like it or not, our world is framed within the work of those that came before us.

It’s important to take a step back from the day-to-day to put your company and your problems into the broader context of the world around us. Practically speaking, this means that you’re likely not the first person to face some seemingly obscure problem. Chances are, some abstraction of the same type of challenge have been dealt with before.

URX is creating a new kind of marketplace for mobile commerce built with a technology that has never existed before. That said, I consider myself a student of the precedents for all facets of our business. From the history of how the internet was born, to the early days of search engines, to emerging mobile business models and their desktop equivalent- I strive to maximize the potential of URX by deeply understanding the world around us.

Kevin Owocki talks more about this in Running a Startup? You’re standing on the shoulders of giants.

“Andrew, this is it — we’ve got the right team, and the timing’s perfect. If we don’t go for this now, we will regret it for the rest of our lives.” I could feel him thinking through the silence. “Alright dude, I’m in. Let’s talk to Nate and James and make this happen.”

Deciding to Go for It

It was a Friday afternoon in mid-January when Andrew, Nate, James and I went from being close friends to co-founders. Looking back, we had no idea what we were getting ourselves into, but our excitement and eagerness was enough to get us started.

I had just stepped out of a meeting with Bruno Bowden, an angel investor I met out of sheer coincidence: after a night out at bars, I dropped my credit card in front of Bruno’s apartment while getting out of a cab. A few days later, I got a LinkedIn message from him telling me he’d found my card. Being the opportunist that I am, I used this as a chance to meet Bruno and pitch him on a few ideas that Andrew, Nate, James and I were working on.

One week, one prototype and two all-nighters later, Bruno became our first angel investor and our journey began.

This experience solidified one of my theories about how the world works: opportunities present themselves in the most curious of manners and it’s each of our responsibilities to create our own luck.

Founding to Y Combinator: the first 90 days.

On my first day as, “John Milinovich, Startup CEO” I was shell-shocked. I stared at an empty GMail inbox, unsure of where to start. The novelty quickly faded to the reality of the situation: I needed help. In the early days of a startup, you are battling inertia: how do you force something into existence that doesn’t exist yet?

I reached out to all of the mentors, friends and peers whose opinions I trusted to better understand how to get started. I was humbled by people’s response- people were so excited that I was going after my dreams and were willing to do whatever they could to help out. This led to several introductions, including to potential customers, investors and advisors.

At first, I was scared to share our idea with people. What if they didn’t like our product? What if they thought it wasn’t useful? What if they actually wanted to use it? I didn’t feel we were ready yet, but decided to put ourselves out there anyways.

This process taught me the most valuable lesson I learned early on: no matter what you’re building or “how early” you are in your development, it is never too early to start talking to potential customers. Customers (or users, in B2C companies) are the lifeblood of startups, and step 0 is to understand their problems and feel their pain. The more customers you speak with, the more perspective you gain — if you hear the same things multiple times, it’s probably something you should take into account.

In mid-April, I had the chance to meet Dave Fowler, the CEO of Chartio. Chartio was one of our neighbors in South Park, and had gone through YC a few years prior. It was a beautiful day outside, so we decide to walk around the Park. We ran into Max Mullen, one of the founders of Instacart (also in YC) and we hit it off right away. I shared a bit about what we were working on at URX, and within 5 minutes Max said, “Yep, that sounds awesome — we would totally use this, sign us up.” Serendipity had played its hand again, and we had just landed our first customer. Our product wasn’t fully built yet, but Max was committed to working with us to fully help us understand Instacart’s needs.

By this point, we had been invited to interview for the Summer 2013 class of Y Combinator and decided to, “make our own luck” and talk to as many YC founders as possible to get a grasp on the interview process. Bruno introduced us to Sumon Sadhu, who founded Snaptalent out of YC’s S’08 class. Sumon is, single handedly, the most talented strategist and persuasive communicator that I’d ever met. He taught us how the Y Combinator interview process works and hammered it into our heads that, no matter what, we need to clearly articulate our 5 Main Points in our interview. We boiled down the entirety of “Why we should be in YC” to five bullet points and committed them to memory.

A few days later we interviewed with Geoff Ralston, Sam Altman, and Garry Tan and it was the most intense 10 minutes of our lives. The interviews are as difficult as they are made out to be, but we crushed it. We got our points across and walked out confident that we had made a good impression. (In retrospect, I’m proud that all of the YC partners we interviewed with ended up becoming investors in URX, along with Sumon).

Y Combinator: The 100 Day Journey

Getting into Y Combinator was a dream come true. Like most young founders, the initial appeal of the program was based on its prestige and the opportunity to quickly gain access to the highest rung in Silicon Valley. For a group of people who understand the value of people and relationships, we knew we were on the right path.

We’d all read Paul Graham’s essays, watched countless YouTube videos about YC, and spent too much time on HackerNews. None of that prepared us for the first time we went on a walk up and down Pioneer Way with PG. After getting into YC but before starting the program, PG meets with all of the startups in the batch. We gave him our quick pitch, and after quickly digesting it he told us that, “We have the opposite problem that most startups face. The opportunity created being able to link into the middle of mobile apps is so big it’s scary. Your challenge is not going to be whether this can be a billion dollar idea, but making sure you don’t get swallowed by it.” Before this we were confident in the opportunity in front of us, but didn’t fully digest how big it could be until hearing it come from PG. This block walk set the tone for the rest of YC- how can we continue to be so big, we’re scary?

At the end of our meeting, PG told us that we need to change our name. It was too generic and not very interesting or differentiated. We spent 20 minutes brainstorming names that better represented our vision than AdLast (our name at the time), and quickly came up with a short-list of 10. URX was at the top of the list but was taken by someone else and had no clear indication of being for sale. We felt like we were at a loss, and admittedly thought we had a lot more important things to worry about than our name.

About a month later, we reported to duty for the first Tuesday dinner at YC. During our first group office hours (a bi-weekly format where 6 startups meet with 2 partners for an hour to discuss updates and challenges), I was introduced to Garry and Geoff outside the scope of our first 10-minute grilling. It’s amazing how similar most early-stage startup problems are to each other, despite all of the surface differences between companies. During that first meeting, Geoff asked a question that has stuck with URX and is now a part of how we evaluate ourselves: What are your bottlenecks to scaling? At any given point, a startup’s growth is inhibited by one of a few things- getting more customers, finding the right market, scaling operations, or technical debt- and by keeping a close pulse on which of these is the largest constraint gives a good perspective on where startups should be applying their limited resources.

During YC, every startup is paired with one of the partners to meet with frequently for 1:1 office hours. Paul Buchheit, the creator of GMail, AdSense and Friendfeed, was our partner. In that first meeting together, we talked about our roadmap, what our customers were saying, and where we saw the biggest immediate opportunity. At the time, we had built a deeplink open source framework and a “bitly for deeplinks,” but had identified that deeplink retargeting was going to be the next frontier. The technology behind a retargeting platform (on either mobile or desktop), is non-trivial to say the least, and during that first meeting PB made us realize that startups don’t get huge by focusing on small wins, but by going for the gold. He told us to stop talking about it and just go do it. We started building and selling our retargeting solution, and quickly realized he was right.

We received an email from PG about a month into YC telling us he’d like to meet because it had been a while since we’d talked last. Excited by the chance to show PG what we’ve built, we booked office hours and prepped what we wanted to talk about. On the familiar walk around Pioneer Way, PG stopped mid-sentence to bend down and pick something up off the ground. It was a mini pine cone from the redwood tree that towered above us. “Startups are like this pine cone,” he told us. “All of them start small and look the same, but only a few will ever realize their full potential.” He handed me the pine cone, and we kept walking. (In case you’re wondering, yes, I still have that pine cone). We continued sharing our plans and he simply shrugged and told us, “Do what will make you the most money first. Use that as your guiding light.” So simple, but more true than we knew at the time.

Towards the end of the meeting, PG gave us a hard time for not yet changing our name from AdLast. We’d looked into it, we told him, but the name wasn’t available. I could see (and hear) his disappointment, and quickly realized that my number one priority had just become our rebrand. 20 minutes later, I was on the phone with the current owner of the name URX and by the time we showed up at the next Tuesday dinner, we were URX.

Demo Day and Beyond

Demo Day is the culmination of the YC experience. It is the reason for the massive time pressure most startups feel during the program and is usually the first time most talk to investors. We had elected to skip the traditional YC PR push about our product in favor of collecting more data, writing the case studies and honing our messaging. In our case, PG also recommended that we stay, “off the record” at Demo Day, meaning that even though we presented no one was allowed to talk about us. This is not the right idea for most startups, but it turned out being great for us. It let us control our own messaging and focus on better understanding the story that we wanted to tell.

I feel fortunate to have been able to pull together our syndicate of investors in 2 ½ weeks. We had about 40 meetings and ended up raising from 31 investors. I didn’t sleep very much and probably took a few years off of my life, but it was well worth it. We had raised about ⅔ of our allocation in the week leading up to Demo Day and were able to filter through the inbound interest post-Demo Day to be very efficient with our meeting schedules. As PG says, once you find your first investors, the rest will follow- this couldn’t have been more true for us.

Now that we’re a fully funded, rapidly growing company, it feels amazing to be able to focus back on our first principles. Not much has changed- we are still “StartupHard,” still focus on our one thing, and are consistently obsessed with scaling and simplifying.

On a weekly if not daily cadence, I make sure to take a step back from things to fully appreciate the reality of the situation. I feel incredibly fortunate to have the chance to work with a rockstar team and have the chance to build something incredible. As my co-founder Andrew recently said, “It’s an interesting challenge to be fully focused on executing while still having the time to appreciate how much has changed in our lives.” It’s so easy to focus on climbing the mountain in front of us that we often forget to look at how far we’ve already come. We have our work cut out for us, but I am incredibly proud of the progress URX has made over the course of the last 9 months.

We’re not sure what’s around the corner for us, but we know that we will be ready for it when it happens.

I feel so fortunate to have spent the last 1 year, 11 months as a student at the most forward thinking company in the world. Working at Google, I was surrounded with incredibly talented people solving difficult problems in a culture of creativity, learning and personal growth.

Today is my last day at Google and, while I am incredibly sad to leave, I am, “uncomfortably excited” about what the future holds. The relationships, experience and skills that I gained during my time at Google have given me the confidence to pursue my dreams of being a startup co-founder.

Some of the most stimulating conversations that I‘ve ever had have been over the amazing food at Beta, Charlie’s or Big Table. I will miss the lunchtime talks and impassioned diatribes more than anything else. There’s no way to explain the culture more than just, “Googley” — unique viewpoints, analytical thinking and creativity flowed through the hallways and was palpable on campus.

Google lets its employees work at an incredible scale at all levels in the company. There are very few organizations that impact as many people and make as much money as Google, and it is absolutely marveling how they make it all work. I’ve had the opportunity to launch new products, build internal programs with global impact, patent new technologies and manage technology partnerships for products used by tens of millions of people. I worked on 20% projects, attended Author Talks, learned Linux, answered customer support questions and filed bugs. Google gave me the freedom to identify and fix the problems with the most impact.

My favorite perk from Google is their investment into the continued education of its employees. Google offers courses to help develop and round out Googlers’ skillsets to help them grow as professionals and individuals. I was able to structure my own curriculum and took 100+ hours of coursework in Python, HTML, CSS, JavaScript, Meditation, Strategic Thinking, Creative Thinking, Negotiations, Data Visualization and Building Authentic Relationships. I received an excellent education and was exposed to new ways of thinking about technology, business and myself all while in the confines of the ‘Plex.

I will always love Google and cherish my memories of my time in Mountain View. I spent some of the most difficult times in my life as a Google employee, and the way they took care of me is something that I will never forget. Google truly cares about its employees and its users and will continue to prosper as long as they keep the spirit alive.

Thank you, Google.