Where is Venture Money in a Market Recession

These past two years, we’ve seen many investors and founders alike lose their pricing discipline. A number of whom believed anything north of a 10-15x multiple was the new normal. Expectedly, it wasn’t here to last. And I fear there may be an overcorrection to revert back to the mean.

Signal was heavily weighted on the names of other investors, whereas it’s now weighted on strictly traction and revenue. As Samir Kaji published not too long ago, “The market reset provides a return to a rational environment where underwriting of deals has shifted away from a “growth at all costs” mentality, and inclined toward fundamental metrics such as margins, capital efficiency, and the current public market comps.”

The pandemic years

I’ve written before why it’s better to get 70% conviction, than 50 or 90%. 50% is a gamble. And for the past two years, investors made many more and much larger gambles than would have been kosher. When capital became a commodity and we saw a convergence of value adds in the early-stage investing world, one of the only differentiators between firms became more capital, better terms, or more introductions. Quantity became the selling point rather than quality. Subsequently, that also bolstered many a founder to take bigger risks.

Companies were overcapitalized. Companies then hired more talent than they needed, which meant, on average, each employee needed to do less work than previously required. It wasn’t rare that we saw the best talent out there working more than one job. In fact, in a study by Nielsen, over 50% of talent worked for two companies without either knowing. As such, we’ve the trimming of fat over the past few months with massive company layoffs.

Very few investors were going to spend an extra week or two to dig deeper – do a little more homework to get the extra 20% conviction. Why? Because if they did, they’d miss the funding window. They’d miss the opportunity to invest in the next big thing.

I also saw many founders working on 10% improvements and features, rather than building robust, 10x, non-cyclical products. Founders rushed to product-market fit, followed by massive injections to put fuel on the fire, as opposed to taking time to A/B test for channel-market fit and minimum lovable products. Founders also became less scrappy with the surplus of capital. Growth at all costs was revitalized as the memo of the future. We were left with a world that too quickly forgot the importance of cash in the bank in the few months from March of 2020 till the summer.

Where is money after the market correction?

Today, investors are going for 90%, much of that on fundamentals, rather than a technical analysis on markets. People have become more focused on the beta portfolios than the alpha in portfolios – not saying the latter isn’t important. It still is.

The good news is that there are still many more dollars to deploy. The nine- and ten-figure funds aren’t going anywhere. The bad news is while there’s technically already money allocated to invest in early-stage companies, they’re getting deployed more slowly. But we’ve seen a slowdown in the deployment of capital. And while capital calls are usually leading indicators of capital deployment schedules, they became lagging indicators in March’s slowdown.

What are capital calls? No LP keeps a massive amount of money parked in a checking account with 0% interest, aka a VC fund. So, capital calls are a VC’s legal right to call forth a portion of the money promised to them by LPs. Usually capital calls are made semi-annually.

Last year we saw capital call schedules rise from 20% to 32%. As such, timelines were compressed. Funds were deployed in 1.5-2 years. I even saw one-year deployment periods. Today, I’m anecdotally seeing funds revert to a 3-4 year timeline.

What does that mean for founders?

You should prepare for the worst. Things may turn out differently, and that’ll be great, but don’t expect it will. Over the next two years, there will only be a third to half as much capital to deploy into private companies. That also means your competition has increased two- to three-fold.

Focus on your gross margins, your customer acquisition costs (CAC), and your burn multiples. For software companies, aim for greater than 50% gross margins. Your CAC payback periods should be at most a year. And get your burn multiple to one. In other words, you bring back a $1 for every $1 you’re spending. If you’re south of that, great! Instead of raising venture money, see if you can use non-dilutive capital, aka revenue, to help you grow. For those, that are still growing north of three times per year on ARR after you hit $1M ARR, then venture capital is a very viable option.

If you’re raising a new round, show that you’ve hit your milestones and that you have a road to your next set of milestones to raise your next round in 12-18 months. If you’re raising a bridge (or preemptive) round, you’re on a tighter schedule. You need to show you can hit milestones deserving of a new round within six months or less.

Sometimes even when you have all the above, investors still won’t bat an eye. So, at the end of the day, I always go back to the sage advice my friend shared with me. Teach your investor something new. Mike Maples Jr calls it the earned secret. a16z calls it spending time in the idea maze. I don’t care what you call it. Investors pay their tuition to work alongside the best. If you want investors fighting over you, you need to show them value from Day 1.

In closing

As Paul Graham tweeted over the weekend, be contrarian.

In the past two years, when people became bullish, I became bearish. I didn’t trust myself to find signal in hot markets. For example, while I believe in the amazing potential of blockchain and the future of web3, I intentionally chose to look at consumer solutions that were not tied to the chain, unable to justify for most ideas, why the chain was necessary to solve the problem. I found many founders stumbling on a solution, then finding a problem to fit in the solution. Rather than the other way around.

Today, I’m more bullish than ever (when others are bearish). An investor will generate much more outsized alpha being in the nonobvious and non-consensus than being in the consensus. And we’re swimming in an ocean of non-consensus today. As Keith Rabois talked about earlier this year, don’t focus on just optimizing for the beta where you’ll only be optimizing for incremental returns. Focus on the alpha.

Innovation is secular to the macro-economic trends. It’s exactly in this time that I’m excited to uncover the next world-defining teams. That said, I’m looking for world-defining insights I’ve never heard of or seen before.

Photo by Jp Valery on Unsplash


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Any views expressed on this blog are mine and mine alone. They are not a representation of values held by On Deck, DECODE, or any other entity I am or have been associated with. They are for informational and entertainment purposes only. None of this is legal, investment, business, or tax advice. Please do your own diligence before investing in startups and consult your own adviser before making any investments.

Why Product-Market Fit Is Found In Strategically Boring Markets

streets, ordinary, boring

In the past decade or two, there have been a surplus of talent coming into Silicon Valley. In large part, due to the opportunities that the Bay had to offer. If you wanted to work in tech, the SF Bay Area was the number one destination. If you wanted to raise venture money, being next door neighbors to your investors on Sand Hill Road yielded astounding benefits. Barring the past few months where there have been massive exoduses leaving the Bay to Miami or NYC, there’ve been this common thread that if you want to be in:

  • Entertainment, go to LA
  • Finance and fashion, go to NYC
  • Tech/startup ecosystem, go to the Valley.

While great, your early audience – the innovators on your product adoption curve – should not be overly concentrated there. All these markets carry anomalous traits and aren’t often representative of the wider population. Instead, your beachhead markets should be representative of the distribution of demographics and customer habits in your TAM (total addressable market).

While Keith Rabois could have very much built Opendoor in Silicon Valley, where more and more people were buying homes to be close to technological hubs, he led the early team to test their assumptions in Phoenix, Arizona. On the same token, Nikita Bier started tbh, not in the attention-hungry markets of LA, but in high schools in Georgia.

“Boring” virtual real estate

Strategically boring markets aren’t limited to just physical geographies. They’re equally applicable to underestimated virtual real estate. You don’t have to build a mansion on a new plot of land. Rent an Airbnb and see if you like the weather and people there first.

As Rupa Health‘s Tara Viswanathan said in a First Round interview, “Stripping the product down to the bare bones and getting it out in front of people for their reactions is critical. It’s rare for a product not to work because it was too minimal of an MVP — it’s because the idea wasn’t strong to begin with.”

As she goes on, “If you have to ask if you’re in love, you’re probably not in love. The same goes with product/market fit — if you have to ask if you have it, you probably don’t.”

Test your market first with the minimum lovable product, as Jiaona Zhang says. You don’t have to build the sexiest app out there. It could be a blog or a spreadsheet. For example, here are a few incredible companies that started as nothing more than a…

BlogsSpreadsheets
HubSpotNerdWallet
GlossierSkyscanner
GrouponStitch Fix
MattermarkFlexiple
Ghost

The greatest incumbents to most businesses out there really happen to be some of the simplest things. Spreadsheets. Blogs. Facebook groups. And now probably, Discord and Slack groups. There are a wealth of no-code tools out there today – Notion, Airtable, Webflow, Zapier, just to name a few. So building something quick without coding experience just to test the market has been easier than ever. Use that to your advantage.

Patrick Campbell once wrote, quoting Brian Balfour, CEO of Reforge, “It’s much easier to evolve with the market if your product is shaped to fit the market. That’s why you’ll achieve much better fit between these two components if you think market first, product second.”

Think like a designer, not like an artist

The biggest alphas are generated in non-obvious markets. Markets that are overlooked and underestimated. At the end of the day, in a market teeming with information and capital and starved of attention, think like a designer, not like an artist. Start from your audience, rather than from yourself. Start from what your audience needs, rather than what you want.

As ed-tech investor John Danner of Dunce Capital and board member at Lambda School, once wrote, “[the founders’] job is to find the absolute maximum demand in the space they are exploring. The best cadence is to run a new uncorrelated experiment every day. While demanding, the likelihood that you miss the point of highest demand with this approach is quite small. It is incredibly easy to abandon this kind of rigor and delayed gratification, eat the marshmallow and take a good idea and execute on it. Great founders resist that, and great investors do too.”

Spend more time researching and talking to your potential market, rather than focusing on where, how, and what you want your platform to look like. Obsess over split testing. Be scrappy.

Don’t fail the marshmallow test

We’re in a hype cycle now. Speed is the name of the game. And it’s become harder to differentiate signal from noise. Many founders instantly jump to geographically sexy markets. Anomalous markets like Silicon Valley and LA. But I believe what’ll set the winners from the losers in the long run is founder discipline. Discipline to spend time discovering signs of early virality, rather than scale.

For instance, if you’re operating a marketplace, your startup is more likely than not supply-constrained. To cite Brian Rothenberg, former VP of Growth at Eventbrite, focus on early growth loops where demand converts to supply. Ask your supply, “How did you hear about our product?” And watch for references of them being on the demand side before.

Don’t spend money to increase the rate of conversion until you see early signs of this growth dynamic. It doesn’t matter if it’s 5% or even 0.5%. Have the discipline to wait for organic conversion. It’s far easier to spend money to grow than to discover. Which is why startup life cycles are often broken down into two phases:

  • Zero to one, and
  • One to infinity

Nail the zero to one.

In an increasingly competitive world of ideas, many founders have failed the marshmallow test to rush to scale. As Patrick Campbell shared in the same afore-mentioned essay, “Product first, market second mentality meant that they had a solution, and then they were searching for the problem. This made it much, much more difficult to identify the market that really needed a solution and was willing to pay for the product.”

The more time you spend finding maximum demand for a big problem, the greater your TAM will be. The greater your market, the greater the value your company can provide. So, while building in anomalous markets with sexy apps will help you achieve quick early growth, it’s, unfortunately, unsustainable as you reach the early majority and the late majority of the adoption curve.

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Why User Hacks Are Awesome to Get to Product-Market Fit

user hacks, product-market fit

I was introduced to a founder of an e-commerce marketplace recently trying to figure out what product-market fit looks like. Specifically what might be some early tells of PMF. And I told him, “If your users are sticking around long enough to try to game your system, you have something they want. While it might not be in the most efficient format, you’re close to PMF. Subsequently, solving that frictional point that users are trying to ‘hack’ will delight them.”

Last year, I wrote that one of the tells of a great unicorn idea is frustration with the status quo. And the lagging indicators of frustration are complaints, but even better, “hacks”. Life hacks. Career hacks. Cold email hacks. Any time a forum or community comes together to share best practices is a potential market opportunity. As Jeff Bezos once said, “Your margin is my opportunity.”

Similarly, if some of your users converge around circumventing your platform, they’re hacking their way to find a better solution. But the fact they’re sticking around on your platform means you have something they want. And while it could be more elegant, you’ve solved the rocks of the “rocks, sand, and water” framework. What’s left are the “sand” and the “water”. And they come disguised as a user hack.

Sarah Tavel of Benchmark once wrote: “You must create an offering that is so compelling, it stands by itself in the consumer’s mind.” Solving all the frictional points in the user journey will get you to that compelling offering – a lovable product.

A reader reached out to me last year and said, “Thank you[But] you have no idea how long I spend reading your blogposts with a dictionary next to me.” While it wasn’t necessarily a hack, to know there was a reader out there willing to weather through my idiosyncratic vocabulary in my earlier essays meant a million to me. But at the same time, it was a sign I was too caught up in my own wordsmithing. So, I dialed it back. While there will still be some esoteric jargon from time to time, I try to make my writing more relatable when editing. And to that reader… if you’re still reading this essay, thank you.

Back in 2007, Marc Andreessen wrote: “The market pulls product out of the startup.” In this case, that pull becomes a race between you and your users’ frustration. Can you release an update that addresses your users’ pain point before they become so frustrated they pack up and go? Either to build their own version or try a competitor’s.

I love Max Nussenbaum of On Deck’s analogy here. “If the market is indeed pulling the product out of you, you sometimes feel less like a creator and more like a mere conduit.” You, as the team behind the product, are a conduit to satisfying your users’ needs. As Mike Maples Jr. says, “Getting storytelling right means the founder is the mentor of the story (ie Yoda), rather than the hero (ie Luke.).” Your customers are the heroes of the story. Of their story. And your story. How they spend their time should offer you brilliant product insights.

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Fantastic Unicorns and Where to Find Them

As a venture scout and as someone who loves helping pre-seed/seed startups before they get to the A, I get asked this one question more often than I expect. “David, do you think this is a good idea?” Most of the time, admittedly, I don’t know. Why? I’m not the core user. I wouldn’t count myself as an early adopter who could become a power user, outside of pure curiosity. I’m not their customer. To quote Michael Seibel of Y Combinator,

… “customers are the gatekeepers of the startups world.” Then comes the question, if customers are the gatekeepers to the venture world, how do you know if you’re on to something if you’re any one of the below:

  • Pre-product,
  • Pre-traction,
  • And/or pre-revenue?

This blog post isn’t designed to be the crystal ball to all your problems. I have to disappoint. I’m a Muggle without the power of Divination. But instead, let me share 3 mental models that might help a budding founder find idea-market fit. Let’s call it a tracker’s kit that may increase your chances at finding a unicorn.

  1. Frustration
  2. The highly fragmented industry with low NPS
  3. Right on non-consensus
Continue reading “Fantastic Unicorns and Where to Find Them”

#unfiltered #27 The Impetus of My Social Experiments – Higher Research and the Application to Startups

bunny, egg, curiosity, curious, social experiments

People seem to love origin stories – both in theatre and in life.

“How did it all start?”

“How did you get into this career?”

Or…

“How did you meet your wife/husband?”

And well, I can’t say I’m one to push back on that.

There’s something truly magical about “Once upon a time…”. And I’m no stranger to fairy tales. Growing up, I was largely influenced by older female cousins and family friends. As soon as our parents left to their wine-sipping adult gossip around a table of blackjack, my cousins and older female friends would drag us to watch their favorite Disney movies on the VCR, namely princess movies. I’m not exaggerating when I say I’ve seen Beauty and the Beast more than 100 times or Cinderella more than 50 times. In fact, my friends in elementary school would talk about their favorite movies – Transformers, LEGO Bionicles, Peter Pan, and Tarzan. Yet, mine was Disney’s 1998 Mulan.

And they all started with “Once upon a time…”

So, it was no surprise when friends, colleagues, and then strangers started asking me:

“How/when/why did you start hosting social experiments?”

Continue reading “#unfiltered #27 The Impetus of My Social Experiments – Higher Research and the Application to Startups”

On Scale – Lessons on Culture, Hiring, Operating, and Growth

flower, scale

One of my favorite thought exercises to do when I meet with founders who have reached the A- and B-stages (or beyond) is:

“What will his/her company look like if he/she is no longer there?”

The Preface

While the question looks like one that’s designed to replace the founder(s), my intention is everything but that. Rather, I ask myself that because I want to put perspective as to how the founder(s) have empowered their team to do more than they could independently. Where the collective whole is greater than the sum of its parts. Have the founders built something that is greater than themselves? And is each team member self-motivated to pursue the mission and vision?

It reminds me of the story of a NASA janitor’s reply when President Kennedy asked: “Hi, I’m Jack Kennedy. What are you doing?”

“Well, Mr. President,” the janitor responded, “I’m helping put a man on the moon.”

From the astronaut who was to go into space to the janitor cleaning the halls of NASAs space center, each and every one had the same fulfilling purpose that they were doing something greater than themselves.

And if the CEO is able to do that, their potential to inspire even more and build a greater company is in sight. Can he/she scale him/herself? And in doing so, scale the company past product-market fit (PMF)?

For the purpose of this post, I’ll take scale from a culture, hiring, operating, and product perspective, though there are much more than just the above when it comes to scale. Answering the questions, as a founder:

  • How do you expand your audience?
  • How do you build a team to do so?
  • And, how do you scale yourself?

And to do so, I’ll borrow the insights of 10 people who have more miles on their odometer than I do.

While many of these lessons are applicable even in the later stages of growth, I want to preface that these insights are largely for founders just starting to scale. When you’ve just gone from zero to one, and are now beginning to look towards infinity.

The TL;DR

  1. Build a (controversial) shocking culture.
  2. Hire intentionally.
  3. Retaining talent requires trust.
  4. Build and follow an operating philosophy.
    • Create, hold, and share excitement.
    • Align calendars.
  5. Upgrade adjacent users as your next beachhead.
  6. Capture adoption by changing only 1 variable per user segment.
Continue reading “On Scale – Lessons on Culture, Hiring, Operating, and Growth”

Video Games – Evolving from Social Networks to Ad Marketplaces

video games, startup gamified models, startup gamification, ads, advertisement market

With the 2020 series of events, many of us have started to look for other ways to pass our time. Some have looked towards Netflix and Disney+. A number, baking (even ice cream making; thank you to everyone who got an ice cream machine before me). And others, gaming. The number of friends, who had no track record of gaming and suddenly started talking about how to farm iron nuggets in Animal Crossing: New Horizons, skyrocketed. Anecdotally, more than 3-4 fold more.

Games = social networks

Games have become the new social networks. I’m not even talking about the gaming subreddits on Reddit or the Discord channels out there. And much like how social networks are communal hubs of interaction, games, like:

…*deep breath* just to name a few, offer just as much, if not more. People spend hours indulging on the platform and interacting with friends. Not only that, because content is native to gaming platforms themselves, it makes it easier for friends to connect and share content on progress and goals. Much like groups and communities on social networks, many games have clan systems that increase retention and engagement on the platform. Games are just sticky.

By the numbers

They aren’t discrete “one-off” purchases, like my old Nintendo 64 cartridge games, but evolving engines of narrative and relief, or as Andreessen Horowitz calls them – living franchises. What started as “one-off” buys became downloadable contents post-launch (DLCs). And looking at games like World of Warcraft, Fortnite, with constant monthly updates, patches and hotfixes, the games you buy “in the box” are no longer the same beast as before. And now we have a term for it all – Games-as-a-Service (GaaS).

In 2019, there were over 2.5 billion gamers in the world. That’s about 1 gamer out of every 3 people in the world. Together, they spent $120.1 billion on games and grew the market 3%, in a study by SuperData. And you know even Neilsen wants a slice of the pie when they acquired SuperData in 2018, a research company dedicated to tracking the game and e-sports markets. No surprise, Neilsen’s not alone. 44.2% of Tencent’s investments have been into gaming – owning 100% of Riot Games (League of Legends), 40% of Epic Games (Fortnite), 81.4% of Supercell (Clash of Clans), 10% of Bluehole (PUBG), and even 1.3% of Roblox and 2% of Discord. Sony, Microsoft, Apple, and many others are no stranger to putting their dollar into gaming as well.

Though many in 2019 weren’t bullish on the 2020’s growth numbers, in hindsight, we’re seeing a whole different wave of optimism. Hell, March 2020 was a real winner for gamers, spending $1.6 billion on games, their hardware, software, accessories and game cards, thanks for COVID. Needless to say, Animal Crossing topped the charts. I can’t imagine the number at the end of 2020.

Social athletes

You also have Twitch streamers, YouTubers, mods, and creators who become the local/global authority on the market and often ubiquitous with the games/genres they play. Who can actively and passively sway how a community thinks and acts, just like big-time influencers on social media. They have effectively become, what I call, social athletes, turning their hobby into a full-time pursuit. And earning paychecks by representing the brand/team they love most, as well as through sponsorships and partnerships. Shroud, a former competitive e-sports athlete, now one of the biggest streamers in the industry and formerly exclusively streaming on Microsoft’s Mixer, took a 1.5 month break after the Microsoft shut down its Twitch competitor, Mixer. And on his first day back recently, he had half a million viewers tuning in to watch his revival on Twitch.

The next frontier

Just like how social networks evolved into ad-based revenue models, games are evolving into a similar beast, as well. Mobile games have been no stranger to advertisements for a long time. But we’re now seeing the change now on PC and console games. And in a slightly different nature. Where the ads are embedded into the game experience itself, rather than the pop-out kinds.

Epic Games’ Fortnite definitely took it all to the next level – from their live, in-game events to their virtual cosmetic options that acted as film promotions. The latter, much like, how LEGO releases a whole series of movie-related sets to help with promoting it. And their live events are no joke, whether it was:

  • Their live Marshmello concert (with 11 million attending live),
  • Their Marvel crossover event where players could play as Thanos,
  • Or, when 3.1 million players got a sneak peek into a never-before-seen scene in Star Wars: The Rise of Skywalker before it came to theaters.

As expected, many other games are following suit. Recently popular PC game, Fall Guys, is now hosting a “battle of the brands” on their Twitter – a bidding war to have your brand featured as a cosmetic in the game towards a good cause of donating to Special Effect, a charity dedicated to helping gamers with physical disabilities.

Last I checked, the bid is at $420,069.69. And yes, I’m sure the numbers were intentional.

So, what’s next?

Well, it’s an exciting time. Not too long ago, influencer marketing blew up. And now brands/games are becoming influencers in and of themselves. Whether that fall under influencer marketing or a new bucket, I don’t know. What I do know is that though we are all far apart right now, the world of media is bringing the larger world closer together. As more games:

  • Go cross-platform,
  • Are discovered organically and socially,
  • And are fueled and accelerated alongside co-creaters, influencers and user-generated content…

… while technologies, like 5G, virtual and augmented/mixed reality (VR/AR/XR), cloud gaming, and blockchain, bring more interactions into each game, building larger and immersive worlds, I’m quite bullish on the growth of the gaming industry. And as the gaming industry evolves, their learnings will bleed into other industries, via gamified models – from Pioneer gamifying the process of building a business to Superhuman gamifying productivity, first through emails.

Why? They’re sticky – high engagement and retention cohorts. And I dare say, sexy, as well. Frankly, game companies don’t just launch with minimum viable products (MVP), but minimum viable happiness (MVH). Or as Jiaona Zhang, VP Product at Webflow and lecturer at Stanford’s School of Management Science & Engineering, calls it: minimum lovable products (MLP).

If you’re interested in a deep dive on how to offer MVH or build an MLP, check out my previous post on the topic:

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Tracking What Customers Love

focus, lens, product-market fit is fluid, how to find product market fit

Product-market fit is fluid. Just because you’ve attained it once doesn’t mean you’ll have it forever. The market is constantly changing. And that means the intersection where supply meets demand will always be changing as well. That said, regardless of how and where you move to, you’ll always have a subset of your customers who aren’t happy. Who might miss the old ways. Who might wish for something else entirely.

To put it into perspective, I’m going to quote Casey Winters (his blog), the current Chief Product Officer at Eventbrite:

“Product-market fit isn’t when your customers stop complaining, it’s when they stop leaving.”

Retention and its Touch Points

If you run a business, you’re going to have a leaky funnel. Your job is to minimize the leaks. Double down on not just adoption, but especially retention. What does that mean? Engagement and the often, overlooked category, for many early-stage teams, re-engaging those that have become inactive over a set period of time. Whether 30 days or 7 days. It depends on what solution your product is providing for the market and how frequently you normally expect them to use the product. For example, for most consumer apps, as investors, we expect a minimum of usage for 3 days out of the 7 calendar days a week. So I characterize inactivity aggressively as after a month of inactivity.

In the past few months, since the health and economic crisis began, the conversation has shifted from ‘growth at all costs’ to profitability. And similarly, from an overemphasis on adoption to a better understanding of retention.

Speaking of retention, 2 days ago, the afore-mentioned Casey Winters and Lenny Rachitsky published their homework on the the dichotomy between good and great retention, which you can find here and here, respectively. Their research provides some useful touch points about “golden” numbers from some of the smartest people in the industry. Of course, as their research suggests, everyone’s “golden” number is different. At different points in time.

So, how are you tracking how lovable your product is?

One of my favorite ways to track what keeps users coming back for more is the Depth vs. Breadth graph. Plotting how long people use certain features and how often they click into it. You can easily substitute length of time (depth) with the number of actions taken for each product feature you have. Or as you grow into having multiple product offerings, this graph works just as well.

depth vs breadth graph, retention, product features

Below are just a few examples of breadth and depth metrics:

BreadthDepth
# of logins/week# actions/session
Session countSession time length
D1/D2/D7/D30 sessions# concurrent devices logged in
Platform-specific sessions
DAU/MAU
# paid users/ # total

The above graph should also help you better optimize your features/offerings. For instance, let’s say you’re a startup in your growth stages. Going by Reid Hoffman‘s rule of thumb for budgeting, spend:

  • 70% on your ‘popular‘ product offerings,
  • 20% on your ‘niche‘ product offerings,
  • And 10% exploring your any hidden gems in your ‘broad‘ quadrant.

In closing

If you have your finger on the pulse about what your customers love about you at all times, you’ll be able to create a more robust product. As a final note, I want to add that while this piece has been dedicated to what your customers love, please always keep in mind what they hate as well. And why they hate what they hate. Who knows? You might discover a larger secret there.

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Part-time vs. Full-time Founders

Over the weekend, my friend and I were chatting about the next steps in her career. After spending quite some time ironing out a startup idea she wants to pursue, she was at a crossroads. Should she leave her 9-to-5 and pursue this idea full-time, or should she continue to test out her idea and keep her full-time job?

Due to my involvement with the 1517 Fund and since some of my good friends happen to be college dropouts, I spend quite a bit of time with folks who have or are thinking about pursuing their startup business after dropping out. This is no less true with 9-to-5ers. And some who are still the sole breadwinner of their family. Don’t get me wrong. I love the attention, social passion, literature and discourse around entrepreneurship. But I think many people are jumping the gun.

Ten years back, admittedly off of the 2008 crisis, the conversations were entirely different. When I ask my younger cousins or my friends’ younger siblings, “what do you want to be when you grow up?” They say things like “run my own business”, “be a YouTuber”, and most surprisingly, “be a freelancer”. From 12-yr olds, it’s impressive that freelancing is already part of their vocabulary. It’s an astounding heuristic for how far the gig economy has come.

Moreover, media has also built this narrative championing the college dropout. Steve Jobs and Apple. Bill Gates and Microsoft. And, Mark Zuckerberg and Facebook. There’s nothing wrong in leaving your former occupation or education to start something new. But not before you have a solid proof of concept, or at least external validation beyond your friends, family and co-workers. After all, Mark Zuckerberg left Harvard not to start Facebook, but because Facebook was already taking off.

Honing the Idea

The inherent nature of entrepreneurship is risk. As an entrepreneur (and as an investor), the goal should always be to de-risk your venture – to make calculated bets. To cap your downside.

Marc Benioff started his idea of a platform-as-a-service in March 1999. Before Marc Benioff took his idea of SaaS full-time, he spent time at Oracle with his mentor, Larry Ellison, honing this thesis and business idea. When he was finally ready 4 months later, he left on good terms. Those terms were put to the test, when in Salesforce’s early days, VCs were shy to put in their dollar on the cap table. But, his relationship he had built with Larry ended up giving him the runway he needed to build his team and product.

Something that’s, unfortunately, rarely talked about in Silicon Valley and the world of startups is patience. We’ve gotten used to hearing “move fast and break things”. Many founders are taught to give themselves a 10-20% margin of error. What started off as a valuable heuristic grew into an increase in quantity of experiments, but decrease in quality of experiments. Founders were throwing a barrage of punches, where many carried no weight behind them. No time spent contemplating why the punch didn’t hit its mark. And subsequently, founders building on the frontlines of revolution fight to be the first to market, but not first to product-market fit. Founders fight hell or high water to launch their MVP, but not an MLP, as Jiaona Zhang of WeWork puts it.

In the words of the one who pioneered the idea of platform-as-a-service,

The more transformative your idea is, the more patience you’ll need to make it happen.”

– Marc Benioff

As one who sits on the other side of the table, our job is to help founders ask more precise questions – and often, the tough questions. We act more as godmothers and godfathers of you and your babies, but we can’t do the job for you.

The “Tough” Questions

To early founders, aspiring founders, and my friends at the crossroads, here is my playbook:

  • What partnerships can/will make it easier for you to go-to-market? To product-market fit? To scalability?
  • What questions can you ask to better test product feasibility?
  • How can you partner with people to ask (and test) better questions?
  • What is your calculus that’ll help you systematically test your assumptions?
  • Do you have enough cash flow to sustain you (and your dependents) for the next 2 years to test these assumptions?

Simultaneously, it’s also to important to consider the flip side:

  • What partnerships (or lack thereof) make your bets more risky?
  • How can you limit them? Eliminate them?

And in sum, these questions will help you map out:

At this point in your career, does part-time or full-time help you better optimize yourself for reaching my next milestone?

A Reason to Stay

Photo by Hayden Scott on Unsplash

In the first startup I joined, we messed up our initial business model by not providing a reason for small- and medium-sized business (SMB) owners to stay. We created a marketplace between SMBs to transact with each other. But, after the first one to three transactions, they had no need for our platform. The scary thing about marketplaces isn’t that you’re connecting suppliers to their demand network, but not providing any bonuses after onboarding – a reason to stay.

Some of the stickiest companies are marketplaces because they provide that reason to stay. More often than not, providing a lovable product so convenient, it’s much easier to use the marketplace platform than to do the transaction themselves, and an easy, passive way to be discovered by future clients/customers that would be much more difficult on their own.

Why Multiplayer Video Games Work

In his book The Messy Middle, Scott Belsky, Chief Product Officer at Adobe and founder of Behance (acq. by Adobe), a discovery platform where creatives can showcase their portfolios and engage with others’, shares that when crafting the ‘first mile’ experience, you need to optimize for three questions:

  1. Why are your customers here?
  2. What can they accomplish?
  3. What can they do next?

Arguably, I believe that founders should always have these three questions hovering above their product strategies, beyond the ‘first mile’, only embedded more implicitly. Video games do an amazing job in this regard, especially massively multiplayer online role-playing games, or MMORPGs for short.

Why play the game? Find escape and sanctuary to be someone players want to be but can’t in the confines of reality.

What can they accomplish? Achieve that endgame that players see in the trailers and in the tutorial (the onboarding for an MMORPG user). The endgame is self-defined as well. Of course, the game optimizes for the power creep meta endgame. Yet, players can always opt for a ‘destiny’, a story, they find compelling, like becoming a fashionista, a wealthy merchant, a mentor, a content creator, and with faster computing systems and more robust infrastructure, a contributor to the game itself, through user-generated content (UGC). The Steam Workshop is an excellent example of UGC.

What can they do next? Level up their character and gear. Tackle the next quest – main or side – towards something larger than themselves. There’s always a defined goal, as well as actionable steps and additional incentives laid out for the players. This creates high retention value – a reason to stay.

The same is true for many other types of genres of multiplayer games – multiplayer online battle arenas (MOBA), battle royale (BR), first-person shooters (FPS), and more. It’s just the narrative of the endgame may change a little towards leaderboard domination. E-sports, content creation, and live streaming then offers a new tier of recognition and endgame for many veteran players.

Back to Marketplaces

I’ve always argued that as a founder, you want to focus on unscalable wins before thinking of scale pre-product-market fit. Focus on the individual experiences. As Li Jin, partner at the reputable a16z, wrote in a post about the passion economy, “[great founders] view individuality as a feature, not a bug.” The best marketplaces, like Uber, Airbnb, and Medium, started off focusing on the unscalable wins for a small individual subset of their potential users. These products offered their early users a reason to stay:

  • (Additional) Incentives and tools, to make their stay worthwhile;
  • Discovery platform to help them grow their brand and customer base, actively and passively;
  • And, subsequent community and network effects.

Early adopters jump on a new product, as fast as they jump off one. They’re finicky. They’re window shoppers, but at the same time, the most willing and likely to try out your product. Luckily and unluckily, the San Francisco Bay Area has no shortage of these folks, and being a tech startup, with its initial user base here, often inflates your early metrics. In short, the goal of your product is to make these technological butterflies fall madly in love with you and your product. That’s the tough part, but it’ll also mean you’ve found product-market fit (PMF).

Where do we find ‘love’?

Instead of a minimum viable product, or MVP, Jiaona Zhang, Senior Director of Product at WeWork, in her First Round Review piece, chases the “pixie dust”, or what I like to call the secret sauce – a truly unique, money-making insight. This magic is found through diligent iteration on consumer feedback, especially in the beta stages of a product. During the beta, users have the serendipity to discover “that magical moment in the user journey where the user realizes that this product is different from anything else they’ve ever experienced”. Her framework, designed from the perspective of the consumer:

Wouldn’t it be cool if users could [a process/action that would 10X their lives]?

What We Learned

The same was true for us at Localwise. Of course, we were motivated by poor retention metrics. But, we learned what businesses truly needed by asking each of them in person, as well as flyering (and getting rejected, or worse, ignored) to college students and to shops. So, still deeply in love with the community we built, we found that need when connecting local talent to SMBs. For businesses with high churn rate with temporary employees and a need to build a brand, that was their reason to stay.