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Is It Normal to Talk to Yourself Out Loud? Reassuringly, Yes. | The Swaddle

I've always enjoyed writing. The idea of effectively communicating ideas, of crystallizing a thought into something I can refer to again and again. I always appreciate well-written ideas because they are atomized concepts that are mixable and re-mixable. But in my life, I've never written consistently.

I hesitated and hawed, skeptical of writing more, but always wanting to. The idea that I held on to for years, and ultimately the thing that pushed me to write more, was this:

"I write because I don't know what I think until I read what I say." (Flannery O'Connor)

That concept always struck me because it represents a truth. So many people hold off on writing, or creating any kind of content, because they don't want to be shouting into the void. We'll never read all the exceptional writing that is out there, so why should we pile on? But the act of writing is the benefit, not just the output.

Sonke Ahrens explained that concept even more clearly in his book How To Take Good Notes:

"There is no such thing as private knowledge... An idea kept private is as good as one you never had. And a fact no one can reproduce is no fact at all. Making something public always means to write it down so it can be read. There is no such thing as a history of unwritten ideas.

The challenge of writing as well as learning is therefore not so much to learn, but to understand, as we will already have learned what we understand. The problem is that the meaning of something is not always obvious and needs to be explored. That is why we need to elaborate on it. But elaboration is nothing more than connecting information to other information in a meaningful way. The first step of elaboration is to think enough about a piece of information so we are able to write about it. The second step is to think about what it means for other contexts as well."

In his summary of the same book, Tiago Forte put it this way:

"Writing is not only for proclaiming fully formed opinions, but for developing opinions worth sharing in the first place."

I've shared a couple notes about what I wrote this year, and what I read this year. Now, I thought I'd take some time reflecting on what I thought this year.

Talking To Myself

After looking back on all my writing, these were the conversations topics that came up most often.

Early in my career, I welcome learning; even if it means suffering
Developing a spirit of humility (being able to recognize you might be wrong) is the key to survival
Not every company is the best company; outliers really do exist
Reflecting on the past is the best way to prepare for the future
The importance of a brand and creating your "vibes" in venture
Venture capital has had very few evolutions
Venture firms will be forced to value the individual brand of the people they work with, or they'll opt to do their own thing
VCs will be on the hook to more clearly articulate their value proposition
Startups are being built on established playbooks and exceptional talent
Your strategy reflects your org chart; for better or worse
Storytelling can rewrite reality; for better or worse
A private company's valuation is as much a story or narrative, as it is a valuation
Incentives are everywhere
Market size can sometimes be all that matters

Below I included some excerpts from my writing that best represent these ideas I kept revolving around.

Early in my career, I welcome learning; even if it means suffering

And maybe I'm just filled with existential self-loathing but I'm early enough in my career that I'm not afraid of suffering. I’d go as far as to say I welcome it. (Taste of Pain)
I've dubbed the people driving those changing forces as "renegades." These aren't just solo capitalists or startup funds. Any fund doing something new and disrupting the status quo in venture can be a renegade. One of my favorite things is to reflect on the impact these people are having. I'm young enough in my career that I welcome radical change. It shakes up the way startups get funded and how companies get built. (Renegade: Lowercarbon)

Developing a spirit of humility (being able to recognize you might be wrong) is the key to survival

I want everyone to be an investor, but I don’t want everyone to be an investor who is convinced they’re a genius. (Taste of Pain)
The first step in getting ready to learn from pain is acknowledging the possibility that you might be wrong. (Taste of Pain)
A herd of people approach investing believing so confidently in themselves, often because "being wrong (and excited) is less painful than being right (but boring)." (Taste of Pain)
The internal monologue running in every investors head is painting them as the hero contrarian laying out what they believe but that everyone else is wrong about. There is an epidemic shortage of people willing to ask the question "what am I wrong about?" (Taste of Pain)

Not every company is the best company; outliers really do exist

It has almost always been true that the very best businesses have a premium valuation (sometimes only slightly so). But when you start to value every company as if it will be one of the 5 best companies ever you'll be disappointed more often than not. Not every company will be Salesforce. (Taste of Pain)
"It is often said that it is "hard to overpay for the best companies." That's true, but my hunch is that the cause of some stress now is investors doubt that they've truly chosen the best companies, and they've potentially bought into too broad a sweep at a local pricing maxima for the power law to work in their favor." (What's in a Valuation?)
"Companies big and small will be [re-]examined through the lens of growth narratives driven by product diversity. It’s no longer good enough to just handle online storage, or to just facilitate online meetings, or to just empower consumers to freely trade securities. The public markets will likely reward those companies who can diversify their product lines into messaging, analytics, gaming, and more — those special companies and business leaders who continue to bundle value into their platforms." (What's in a Valuation?)
But there is more going on than just keeping a handle on your mental wellness as a founder. There is a legitimate economic bifurcation between companies. This is happening in public and private markets where the divide among companies between the best and the rest is becoming more defined. (Tale of Two Markets)
Investors are being required to justify the long-term potential for the businesses they invest in. Sustaining and even accelerating revenue growth is a key part of that. (Tale of Two Markets)
Great founders who accept the responsibility of taking on venture money are also smart enough to understand the minuscule statistical likelihood of becoming one of those massively successful "best-in-the-world" companies. (Tale of Two Markets)
I think it's fair to say that a company is more of a natural thing that is always at the precipice of death. Acknowledging the potential for death is the first step in building a business that can defy the odds and not only survive, but thrive, for as long as possible. (Natural Selection Among Startups)
In climate tech this is an even more important debate. There is not only limited time but limited resources to build the most impactful solutions. In the not too distant future investors are going to have to face a reckoning of whether they're funding "feel good" climate-adjacent companies or genuine impact. (Renegade: Lowercarbon)
Different idealogical templates for how to think about a business, how it will scale, the things they need to do, and the likely outcomes / upside all help form heuristics for what we can expect. These are like Da Vinci's rules of art. But instead of becoming academic, and believing those generalized rules are the only reality? We can instead look for the reality of the unrealistic outliers. (Unrealistic Outliers)
These are the kinds of examples that people should constantly be looking for, and studying: businesses that can defy gravity. Study the commonalities in how these companies’ unique positions set them up to defy any of these standards and rules-of-thumb. (Unrealistic Outliers)
A lot of people are ready to jump up and down on these failures and even use the outcome as evidence of a bygone conclusion. But most of the time these are companies that got built around a lot of good ideas that just turned out to be wrong. And often investors are the fuel on the fire that is raging in the wrong direction. (Outcome Distortion Complex)

Reflecting on the past is the best way to prepare for the future

In a market where very little has gone wrong there isn't always as strong a pull to reflect. No one ever found themselves staring into the abyss wondering what went wrong after they just 5x’ed in one year. When looking backwards everyone sees their decisions as a well-measured journey driven by unique insights. Any investor would benefit from an additional dash of accountability. (Taste of Pain)
Times like these are good opportunities to reflect. The last few years VCs and founders have mutually agreed to accept higher and higher valuations. Whether it’s because we believe markets are bigger than expected or companies can grow larger and faster than expected. Whatever your reasoning for paying ever higher valuations it has been an easy thing to do because you would almost always be right. There would always be a markup. That may be less true today so sit back and reflect on your mental frameworks. (What's in a Valuation?)
If the recent market correction has made you question the quality of the companies you've invested in then it isn't the companies you should re-evaluate. It's the process you used when deciding to invest. (What's in a Valuation?)
The reason people don't learn more effectively is because when they're right they're too busy telling people about it to reflect on why they were right. And when they're wrong they're too busy finding someone else to blame. (What's in a Valuation?)
What has always confused me is how rarely venture investors evaluate their own decision making mechanisms. So much is made on gut. If you ask a typical VC why they passed on some of the biggest companies of the last decade most of them couldn't give you a good answer. And they likely couldn't point to how their processes have changed to avoid similar mistakes. (VCs Suck at Talent)
As I spent time thinking about the most common causes of death for startups I found countless resources. The key takeaway for me? Live with paranoia in the back of your mind. Every founder and investor should be curious when they see a founder, startup, or project fail. They should be eager to ask the question "what went wrong?" No failed experience is wasted if someone learns something from it. (Natural Selection Among Startups)
Without a framework for evaluating their own heuristics investors are left to gut-ridden guesswork. A culture of evaluating the good and bad decisions a group has made is a natural result of an effectively crafted organization. And the rampant lack of that reflective culture among most VCs is indicative of the shoddy organization most of them have. (Fantasy Capital)
The less time people spend with failure the less comfortable with it they become. They develop an aversion to the very concept of correction. Acknowledging that something went wrong is to acknowledge that there is blame to be dished out. Particularly in investing there is a lack of easy attribution, both for success and failure, and careers are made or broken based on an investor's ability to take credit for success and avoid association with failure. But there's a better way. The more people can start out with a spirit of humility, execute on their investments under close observation, and reflect on them with an attitude of learning the better off they are. (What's in a Post-Mortem?)
Like the famous quote from John Maynard Keynes: "when the facts change I change my mind." But guess what? Nobody. Changes. Their. Mind. I am convinced that one of the single greatest blockers to social and economic progress is as simple as this: if more people changed their mind when presented with new information we would quickly have even more information with which to improve our thinking. (What's in a Post-Mortem?)
Intellectual honesty is something that is surprisingly difficult. For a combination of reasons: incentives, misunderstanding, ego, public pressure. When people are placed in situations where there isn't as much objective reality (i.e. either something works or it doesn't) it can be quite easy to slip into intellectual dishonesty. Investing in startups is a place without as much objective reality. (Being Honest About Intellectually Dishonesty)
Roelof Botha brought up this same topic in a recent Invest Like The Best episode in an even more poignant way: "Imagine the venture business in a decade, and Sequoia is gone. We presided over the decline of Sequoia, this team, the people here in this room, it was us. What happened? What did we not do?" I loved this concept of evaluating your own potential cause of death as a venture firm. And after reflecting on it for a while I thought, "if Sequoia, who is arguably the best venture firm in the world, is considering their own demise within a decade, then everyone should be doing that." (Death of a Venture Fund)

The importance of a brand and creating your "vibes" in venture

Some of the most recognizable people in the world are right up there with the most recognizable brands like Nike and Coca-Cola in their influence. (Unbundling of VC)
Successful influencers are perceived as genuine, sincere, and most of all, transparent. They differ widely from institutions built during the industrial era. (Unbundling of VC)
The reallocation of trust from brands to individuals is impacting the way founders view the types of investors they want to invite into their companies. The influence within venture has progressively decentralized away from the core brand into renegades leveraging the power of their own brand. (Unbundling of VC)
No VC should ever be famous; at least not for allocating capital. People with ideas that shape cultures or who build technology that changes lives: those are the people that should be celebrated. Venture capital is a tool to help spread impactful ideas. The renegades are recognizing the opportunity to take their own philosophies and change the way ideas are funded. (Renegades of Venture)
While they had interest from traditional VCs they recognized they'd built a business that was sustainable and serving an intense demand even without VC dollars. As a result they were able to skip the traditional VC game and work directly with founders who had perfect empathy for what Synthesis is building and didn't require 20% of the company to justify a round. (Renegade: Synthesis)
The most important thing to do, far in advance of needing to reach out, is to communicate your vibe online. Writing, tweeting, making videos or doing podcasts. My biggest struggle with creating content online was feeling like it would just be shouting into the void. But when you start having lots of these conversations, you realize that these conversations get easier when you have a body of work to communicate your interests and perspectives, in hopes of attracting like-minded people. (You Know Who You Should Talk To)

Venture capital has had very few evolutions

When the VC industry first got started in the 50's and 60's it was 20 people, all connected to Arthur Rock, a lot of whom were related. Fascinating enough, since then the names that started the show are a lot of the same ones who are best known today. (Unbundling of VC)
But by and large venture has stayed the same since its earliest days. Big monolithic brands used by founders as a short-hand for quality whose decisions are controlled by an investment committee behind closed doors. (Unbundling of VC)
Since the old guard of VC firms got started they've largely stuck to the same legal structure: a general partnership. Over time firms have consolidated and added more structure or pieces. What is most interesting is that the core dynamic has stayed the same. The focal point of the partnership is (surprise) the partners. (Productization of VC)
Here's my hot take: venture capital can't just stay a services business. Competition is already going to limit returns, both through less available allocation in the best companies and higher entry prices. Venture capital is going to have to evolve. (Productization of VC)
I've been working in venture for just over seven years. I've loved it. I love working with founders and thinking about how companies get built. I've never considered myself the very best at anything. But what I am is observant. And when you're observant the thing you hate the most is inconsistency. Venture capital is inconsistent. There are some people who hate VCs and think the whole system is bunk. I'm not in that camp. But there are also some people that think venture has been a cottage industry for decades with a lot of participants who believe themselves to be the protectors and deliverers of innovation while sitting on one of the most under-innovated models that exists. I am in that camp. (Renegades of Venture)
Founders want something different. VCs can dismiss things like crypto or climate tech. But guess what? The smartest people are tackling those areas with or without you. But hey. Your old way of doing things is comfortable. So stay there while the world moves on without you. Disruption doesn't come from new technology. It comes from unhappy customers. (Renegades of Venture)
Any venture firm that isn't paying attention to dynamics like this: a world-class company, growing revenue dramatically, effectively profitable, a huge market filled with tailwinds, and no interest in your "ownership thresholds?" There is no clearer sign that the world of venture is changing rapidly. (Renegade: Synthesis)

Venture firms will be forced to value the individual brand of the people they work with, or they'll opt to do their own thing.

You often see the monolithic brand mothership start to crush the spirits of highly qualified partners. For a lot of these people they'll eventually reach a breaking point and they'll either look for a firm acknowledgement of their own value (their own Magna Carta) or they'll strike out on their own. (Unbundling of VC)
As firms have grown in the kinds of things they do they've maintained this religious focus on "the partnership." Even when you have incredible data scientists, researchers, marketers, recruiters, or sales people join these firms? They bend to the will of "the partnership." Never mind that none of the partners have built a data pipeline before. Or have never run a marketing campaign. Or run an executive talent search. What the partners say? Goes. (Renegades of Venture)

VCs will be on the hook to more clearly articulate their value proposition

But again, this isn't about solo capitalists who can only swing so hard. Renegades will show up in all shapes and sizes. Their ability to win deals will depend on the value of their product. (Unbundling of VC)
For every unhelpful VC there is a story of an investor helping to make a game-changing hire or introduction. There is no binary yes or no answer to the question "are your investors helpful?" It's all a question of the quality of the product any investor can offer. (Unbundling of VC)
Every firm is a product. They have a collection of SKUs. They need to ask if they have good product-market fit. Because if they don't they’ll be in trouble. (Unbundling of VC)
The focus on "partners" in VC funds has largely defined the value proposition of each individual firm. Most people would point to the differentiated perspective, personality, or experience of the individual partners that you're taking on. There are around 2,000 venture funds in the US alone. How are they doing differentiating? (Productization of VC)
The reason for venture firms to consider how to more effectively productize their offerings is tied to the increased number and diversity of opportunities. From the explosion of international startup ecosystems, remote work mixing the groups of talent, and complex new categories from AI to robotics to web3 to climate tech. Funds will find themselves exposed to more opportunities and either they specialize (a product in itself) or they productize. (Productization of VC)
The world is changing to become more dictated by value proposition because it reframes the question. What do founders want? They don't particularly care what stage or sector you want to focus on. They want to understand what you can do for them. Sure, being really good at seed or the very best at a sector can be a value offering. But it can't just be a filter. It needs to be a feature. (Productization of VC)
The point of creating a product is not to make it everything to everyone. A lot of firms feel like they have to add the latest and greatest value offering to keep up. This can confuse an already fuzzy view that founders have of a given firm. Building your firm with a product in mind allows you to more clearly articulate your value proposition. What's the "job-to-be-done" that a founder hires your money for? (Productization of VC)
At Homebrew the core value prop of the firm has stayed pretty similar for almost 10 years. A hands-on seed fund writing a small number of checks to enable their close involvement with the companies they invest in. Some venture funds sometimes do mental gymnastics around who they really serve, talking publicly about the importance of founders while also recognizing the need to continue building AUM and keeping LPs happy. But Homebrew has been clear since day one: “We look at entrepreneurs as our customers." (Renegade: Homebrew)
Homebrew has historically offered one product SKU. "Being the seed ‘investor of record,’ which meant we were working with a small number of founders, beginning at a very specific stage." With their new model they've clearly defined their new SKU. (Renegade: Homebrew)
When you look at Homebrew's unique value proposition you see over and over again this guiding principle of more effectively improving the odds of their portfolio company's success. They've defined their service offering around what can most effectively serve up those insights to their companies. (Renegade: Homebrew)
The core job for a VC is helping founders improve their odds of success. In the olden days just helping founders access cash was a helpful tool. Times have changed. Capital is table stakes. So VCs have had to get more thoughtful in creating the product they offer to founders. This has extended to talent, business development, marketing, governance, etc. (Renegades of Venture)
I can't emphasize enough how different that product is. When most venture firms are trying to be everything to everyone Paradigm took a different approach: try to be everything for a very specific someone. (Renegade: Paradigm)
There are a lot of firms reinventing themselves to better fit the ways the world is changing. It isn't just about paying high prices its figuring out how they'll differentiate themselves going forward. (Fantasy Capital)
When I talk to folks who are either building newer firms or those who are attempting to improve the way their current firm offers value I often see this sentiment: "The idea that founders shouldn't expect their investors to add value should change. There should be a reaction to actually delivering results." (Tales of Their Usefulness)
What is so unique about this model is that TheGP is only making a handful of investments per year and with each company they lay out a specific roadmap for what a successful relationship looks like. No venture fund lays out as clear a path forward as that, they typically just have a laundry list of things they could "maybe possibly hopefully" do for you. (Renegade: TheGP)
I've been fascinated by this idea of a "value-add audit." There is no real tangible way to do this today, which is shocking to me. When you consider the fact that we've invested over a trillion dollars of venture capital in the last 10 years and there isn't a very clear attribution model of dollars to success? That's insane. (Renegade: TheGP)

Startups are being built on established playbooks and exceptional talent

We're seeing the professionalization of startup investing as an asset class. The risk of starting a company has gone down and big money has caught onto the absolutely mind-blowing potential returns that some funds have seen and they want a piece of the pie. (Unbundling of VC)
Talent is quickly becoming the final frontier for tech companies. Open source software, GTM playbooks, and thousands of experienced advisors and investors have decreased the need to reinvent the wheel. Talent, on the other hand, is a zero sum game. (Tale of Two Markets)
Creating a talent vortex sounds like something everyone will say they have but very few companies actually do. When you ask the smartest people you know "where are the smartest people YOU know going to work?" you can't fake it when the response starts to get consistent. (Tale of Two Markets)
With the dramatic race forward in technology you’ve seen an explosion in the number of people who can build and scale technology companies. In just the last few decades we've gone from a small group of hobby hackers to a professional workforce of highly trained tech employees. (Professionalization of Startups)
If you step back and look at the breadth of startup experience that people have today you'll start to appreciate two things. First, it's impressive the kinds of incredible experience people have now built up. And second, we're really just getting into the first generation of that experience being widespread. (Professionalization of Startups)
There is a growing population of people that have learned the lessons of the last few decades through their experience building the greatest generation of technology companies in the history of mankind. And as those lessons get distilled to a broader group of people we no longer have to spend so much time reinventing the wheel. Progress comes out of learning from past experiences. And it comes more quickly when those lessons are effectively distributed. (Professionalization of Startups)
These are the people that build the future. No one who has been the visionary founder would disagree with the game-changing role these people play in turning that vision into reality. As the art of building technology companies has progressed and become more demystified it has become easier to see the people who make things happen. These are the people to watch. (Professionalization of Startups)
Many VCs pride themselves on their pattern recognition. They've seen so many different companies come and go that they've honed their sense of what "good" looks like. But the vast majority of investors have some fundamental weaknesses when it comes to identifying and appreciating high quality talent. (VCs Suck at Talent)
The reality is talent is becoming one of the most critical and potentially limiting factors in a company's success. As useful as VCs believe themselves to be the most significant thing anyone can do to make a company successful is to get the smartest people to tackle the right problems in the right way. (VCs Suck at Talent)
I have a secret for you. Very few investors have a good framework for what good talent looks like. The problem with unchecked "gut-trusting" is that you leave yourself exposed to a whole host of psychological bias' and disconnected feedback loops. When you don't have a framework for how you invest or what "good" talent looks like you can't effectively learn from your own experience. (VCs Suck at Talent)
People want to associate, but very talented people want to associate with other very talented people. I've written before about talent vortexes; this idea that a talented group of people starts to become self-perpetuating. (Talent Vortexes)
As an investor one of the most critical things you can do is identify and support the companies run by the smartest people who are getting the best people into the best positions to drive success. There is a lot to learn when you identify pools of talented people and why they came together. (Talent Vortexes)
There is a particular kind of person that is drawn to a culture that focuses on the quality of the learning experience over the size of the paycheck. Smart people want to associate with smart people because they know they can trust them to find the best solution, and that they themselves will be held to the highest standard. That's how talent vortexes are born. (Talent Vortexes)
Identifying the right initial people to kick off a talent vortex is crucial because the first 10 people who get hired will likely hire the next 90. In terms of identifying the most crucial characteristics of those critical contributors, Keith Rabois talks about this idea of "barrels and ammunition." The key idea is that most people are actually mostly good ammunition; high quality but require something to point them in the right direction. (Talent Vortexes)
Stripe who, in addition to being an index bet on digital payments, is making an index bet on their people. Between Patrick and John Collison and Stripe directly they've invested in almost 100 companies, many of them founded by Stripe alumni. Their talent funnel has given them a unique index on high quality people. (Index Bets)
Contrary was built around a key insight that you can build a lifelong platform to invest in a person even before they start a company. I've written about about the incredible pool of talent that exists in tech today unlike any other time in history. New talent vortexes are getting built but they’re few and far between. (My Renegade of Choice)

Your strategy reflects your org chart; for better or worse

Structure your organization around productization. Like I said, the center of a VC firm's universe has always been the partnership. They dictate how everything works. Maybe start to borrow from an org structure that has created phenomenal products. (Productization of VC)
Lowercarbon is a whole new level of commitment as a specialist funds. There are a lot of people that believe specialist funds will struggle to generate the same massive returns that generalist funds can achieve. Having scientists, PhDs, and policy people on staff is a new way of doing things. I love thinking about innovative new org charts in venture, and Lowercarbon's is certainly unique. (Renegade: Lowercarbon)
This fundamental immersion in the frontier of crypto required an entirely different org chart than most traditional venture firms. The way Paradigm has built their team is, I believe, going to be something people point to for decades as the starting point of a fundamental shift in how all venture firms are structured. (Renegade: Paradigm)
I can't emphasize enough how much Paradigm's org chart will change the way they're able to innovate as a firm. We're moving out of the age of a handful of old white dudes around a table with identical backgrounds telling everyone else what to do. The caliber of people working at Paradigm have passed up opportunities to work at some of these game-changing crypto companies because they're valued as contributors at Paradigm. No one is going to do that if they just have to go cow-toe to whatever a GP decides he wants them to do. No world-class engineer is going to go to a firm just to be bossed around by someone who hasn't built a product in 10+ years if ever. (Renegade: Paradigm)
A lack of clarity around the org chart creates problems for both investors and the talented people these firms have brought on to help their portfolio companies with things like recruiting, marketing, and business development. The closest analogy for what venture funds look like today would be a company run by a committee made up of the sales team (investing) who dictate the strategy to every other organization. (Fantasy Capital)

Storytelling can rewrite reality; for better or worse

If you had a hedge fund analyst and a venture capitalist on a game show you could ask the question "a company's valuation is primarily based on BLANK." The analyst might say "the cash flows that a business will produce in the future." The VC's answer? "The narrative." (What's in a Valuation?)
As an investor you're trying to use a valuation to balance risk and opportunity. If you look at the bull and the bear case you're looking at a wide range of possible outcomes. You have to ask the question, "what do I believe?" (What's in a Valuation?)
Your attitude towards money will always have more impact than how much money you actually have. For better or for worse. (Cash: Kingmaker or Killer)
Companies have to adjust to the level of scrutiny and interest from the outside world. People become invested in the stories and then they become invested in how the game is played. The same thing is happening in venture capital. (Fantasy Capital)
I've written before about the storytelling of investing, and how important a narrative is in evaluating an investment. Dan Loeb said being an investor "is to live constantly at the intersection of story and uncertainty." But unpacking that story comes later; dreaming the dream is letting yourself optimistically imagine what could be true, and then seek to help bring it about. (Learning To Dream)
I was excited to help build Contrary Research because I love company storytelling. Every company deserves to have their story told, but that's not an easy thing to do. There's no Bloomberg terminal or quarterly filing that shed enough light on these companies. But does that mean telling their story is impossible? (Open Source Knowledge)
“The way we construct our consciousness is to tell the story of ourselves to ourselves, the story of who we believe we are. I feel that a really public shaming or humiliation is a conflict between the person trying to write his own narrative and society trying to write a different narrative for the person. One story tries to overwrite the other. And so to survive you have to own your own story.” (Being Honest About Intellectual Dishonesty)
There is a quote floating around in my head that I've never been able to find again. The basic idea is this: "Bad ideas with strong support will often do better than good ideas with poor support." As uncomfortable as many people may be with storytelling impacting outcomes the reality is storytelling is a weapon that can be wielded for good or evil. (The Storytelling of Investing)
But planning is an exercise in storytelling. Articulate the story that you genuinely believe (not just the one you're selling to candidates, customers, or investors). And then constantly evaluate that plan to identify the dependencies you have. (All According To Plan)

A private company's valuation is as much a story or narrative, as it is a valuation

On the one hand a private valuation, even more so than a public one, is a function of supply and demand. As Post Market likes to say, “VC rounds are priced. Not valued.” Any competitive funding round is, by nature, under-valued. As Peter Thiel points out, the clearing price in venture is rarely satisfied. (What's in a Valuation?)

Incentives are everywhere

There is no real tangible incentive for venture investors to mentor anyone. "No one trusts each other and you don't know how to sort through people. So you let these people prove themselves until you trust them. And you usually don't really trust them until you've already established your own career. Trust is a luxury." (VCs Suck At Talent)
Venture capital is a constant balance between a company's completely unpredictable lifecycle and a fund’s very strictly contractual ~10-year lifecycle. By removing the typical LP relationship Homebrew has more directly aligned incentives between themselves and the companies they support. With Satya and Hunter as the sole LPs they just have their own money and the returns their effort generates to incentivize them. (Renegade: Homebrew)
"I want to sell to people who are acting out of sheer self interest. We have maybe 200 million people who will think about climate when they make a purchase decisions and I need to get 7 billion more. I'm not going to get all these people on the planet to pay a premium out of just consciousness. I just have to offer them a better product. Guilt and shame aren't going to cut it." (Renegade: Lowercarbon)
Most firms will tell you they emphasize collaboration. They'll tell you they work to incentivize every aspect of the job of serving founders. But by and large firms have setup systems that force everyone to seek visibility and credit. (Renegades of Venture)
The partnership structure forces people to focus on making sure they're getting credit for as many good deals as possible. Where are the incentives for training the next generation of investors? Building better processes for tracking companies? Creating networks for supporting founders? Again, that top-line focus can work if you're just incentivizing the sales team. But that's not how you build an organization! (Renegades of Venture)
I can't stop thinking (and ranting) about how much this is like if the only way to progress in a company was for engineers or designers to eventually pivot to being on the sales team. If the best incentives in your company are around generating revenue then the only way to be successful is to "be a salesperson." (Renegades of Venture)
Every time a company celebrates a title change they "undermine the perception of the company as a meritocracy." The focus should instead be targeted on finding and amplifying those great people who are focused on the scope and impact of their work. Not titles. (Talent Vortexes)
On the one hand, founders can be visionaries who see the future as they shape it. They can execute relentlessly and, when left to their own devices, can remake the world. On the other hand, founders are also human. And as humans they're subject to their own biases, incentives, and heuristics. Those can often lead them down a rough road. (Stewards of Capital)

Market size can sometimes be all that matters

Anyone who doesn't recognize the fundamental shift that climate change represents isn't paying attention. These are the biggest markets that exist globally. Transportation? Everyone that moves. Agriculture? Everyone that eats. 50 years from now we'll either be marveling at the way climate tech innovation changed the way we live and dwarfed the outcomes from investing in software and internet companies or we'll be wishing it had as we watch sea levels rise and large swaths of the planet become uninhabitable. (Renegade: Lowercarbon)
This is such a better principle to have in mind as people build climate tech. Don't rely on people's guilt because it will dramatically limit your TAM. Go find the greediest climate deniers out there and build a solution that they can't help but love. (Renegade: Lowercarbon)
In building a business there are no sure bets. You can have the most tenured executives, the most advanced technology, the strongest tailwinds, and the most direct access to capital and still fail. You can also have little more than an idea and a computer but still be wildly successful. Cash can only ever be a part of the equation. (Cash: Kingmaker or Killer)
Valuation, growth, burn, and ambition are all a function of the size of the opportunity. High valuations, high growth, high burn, and large ambitions are all pretty foolish if the opportunity is small. But sometimes? The opportunity turns out to be so big that it was foolish not to pursue them more aggressively. (Markets, Markets, and Markets)
Whether you're an investor or not the more you can build up an understanding of different trends the more you'll start to see patterns that can be applied in other areas. Whether with other companies, or in companies you want to start. Understanding the headwinds and tailwinds in life make you a much more informed participant. (Tailwinds)
Many people laude the success of zero to one companies. When you've built "something" from nothing it really is exceptional. But just as difficult as it is to be something its also difficult to build "something else" for the first time. Becoming a multi-product company is an intense journey. Bucco Capital calls this capability "economies of scope." The ability to expand TAM by introducing new products. (Building a Product Engine)

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