The Sociology of Business newsletter: the Cadence edit

Newsletter Challenge, v. 9

Quick note: I recently wrapped up a writing coach arrangement with Ari Lewis, host of the Mastering the Attention Economy podcast. We enjoyed working together (see Ari’s ROI here), and he proposed I take on a newsletter editing challenge.

The challenge: Twenty edits by 22 September.

My primary goal: add clarity, concision, and cadence to the newsletters, and sharpen up my own editing process. At the end of the challenge, I’ll provide reflections on each edit and offer some lessons you can use on your own newsletter.

For details on my process, click here, a Google doc. Leave suggestions as you see fit. Thanks!

The 4Cs of the Modern Brand, the Global Pandemic Edition,” Apr 20

@ https://andjelicaaa.substack.com/p/the-4cs-of-the-modern-brand-the-global by Ana Andjelic / @andjelicaaa

–Grey typeface: Ana.

Normal typeface: me.

Key metrics (original -> edit)
–reading level: 12 -> 10.
–word count: 1345 -> 1437
–median sentence length: 19 -> 14 words.
–sentence length, standard deviation (basically, a measure of the variety of sentence lengths): 11 -> 10.


“The 4Cs”: the Cadence edit

Helena Glazer is a fashion and beauty influencer who goes under Instagram handle @brooklynblonde1. On March 30th, she posted a photo of herself in the head-to-toe Everlane look, a mere couple of days after Everlane fired all of its union workers and was publicly called out for it by Bernie Sanders. Helena Glazer is a fashion and beauty influencer who goes under Instagram handle @brooklynblonde1. On March 30th, she posted a photo of herself in the head-to-toe Everlane look, a mere couple of days after Everlane fired all of its union workers and was publicly called out for it by Bernie Sanders. 

On March 30, fashion and beauty influencer Helena Glazer posted a photo of herself on Instagram fully clad in Everlane apparel and, nearly instantly, discovered the contemporary perils of cluelessness. Three days before, Everlane had fired their workers who were trying to unionize. Senator Bernie Sanders drew attention to the kerfuffle and rightly so, given Everlane’s tagline: “Our way: Exceptional quality. Ethical factories. Radical Transparency.”

~~~~~~

Both in her website post and in her Instagram comments, she was called out for supporting a brand with the obviously unethical practices. “Maybe reconsider supporting Everlane. They are under heat and controversy for laying off their workers for wanting to unionize, which says a lot about Everlane,” one Instagram comment read. “It’s hard for me to even consider buying anything from Everlane having in mind their latest choices and horrible behavior … It’s interesting to see how affiliate bloggers are gonna approach the situation,” was one of the comments on the Brooklyn Blonde website. Under pressure, BB later clarified in her Instagram Story that she was “not aware” of what happened and was under contractual obligation with Everlane to promote their products.

On Instagram and her website, Glazer got called out for supporting a brand with apparently shady ethics.

“Maybe reconsider supporting Everlane,” noted one Instagrammer “They are under heat and controversy for laying off their workers for wanting to unionize, which says a lot about Everlane.”

“It’s hard for me to even consider buying anything from Everlane having in mind their latest choices and horrible behavior,” noted a message on her website. “It’s interesting to see how affiliate bloggers are gonna approach the situation.”

Glazer later clarified that she was under contractual obligation to promote Everlane products and was “not aware” of their anti-union stance.

~~~~~~

These days, this particular kind of practiced cluelessness draws ire, as Page Six-labeled #covidiot Arielle Charnas experienced first hand. Almost overnight, consumers went through the cultural climate change and emerged on the other side more receptive to brands’ and influencers’ positive actions and more ready to scrutinize the perceived negative ones. Selfishness, insensitivity, inequality, lack of empathy and compassion, and failure to read the room are quickly socially shamed.

These days, this variety of practiced ignorance can be deadly for brands. Consider “#covidiot Arielle Charnas,” who, according to the New York Post, “used ‘her privilege’ to obtain one of the treasured [COVID] tests — even after she had said she didn’t meet the criteria.” Almost overnight, consumers went through this cultural climate sea change. Now, on the other side, they scrutinize the ethical actions of brands and influencers, and they’re instantly ready to shame those who traffic in selfishness, insensitivity, inequality, and lack of empathy.

~~~~~~

This is the new backdrop for brand strategy. Radical individualism is out, social connection is in. Brand focus is not on the end customer, but on the communities they belong to. Just as personas made individual consumers visible, the new brand methodology makes visible consumer communities and their co-dependencies and influences. New focus of engagement plans is not just on the brand actions, but on their secondary effects. Pre-pandemic consumer-centric brand strategy is now society-centric strategy.

Against this new backdrop, there are the 4Cs of the modern brand: community, content, curation, and collaborations. They impact how a company defines and executes their brand strategy, launches and markets its products and services, and captures, distributes and delivers value to its customers.

 Welcome to the new backdrop for brand strategy. Radical individualism is out. Social connection is in. Brand focus now shifts from the end customer to the communities they belong to. Just as personas made individual consumers visible, the new brand methodology makes visible consumer communities and their success in walking the walk. Engagement plans need to account for brand actions and their secondary effects. Consumer-centric brand strategy is so 2019. Society-centric strategy rules the era of COVID-19 (and after).

Let’s imagine there are 4 Cs for contemporary brands: community, content, curation, and collaborations. All four impact how

a company defines and executes their brand strategy,

launches and markets its products and services, and

captures, distributes and delivers value to its customers.

~~~~~~

Community. A brand community quickly went from a “nice to have” to a “must have.” It doesn’t matter what category a brand is in, it has to find a way to put forward its social mission and values, which are the gel for a community. For brands that already maintain communities, the next step is to activate it more, and more often. Marc Jacobs’ WFH and Drawn Together, and GANNI Talks are examples of capitalizing on a brand’s own creative community. Or, MeUndies is these days featuring customers willing to share selfies wearing MeUndies products on instagram. David Zwirner gallery partnered with the wider gallerists’ community and launched Platform: New York, an online initiative to feature artists from twelve NY-based galleries. Allure magazine activated its community of stylists, makeup artists, photographers, and hairstylists. Or, going beyond its immediate readership, TIME Magazine launched TIME for Giving, a community of those keen to provide assistance to a list of charities and causes in need. The key here is for brands to stop thinking about their community just as top-of-the-funnel tactic, and consider it as a long-term, bottom-of-the-funnel strategy (bonding, advocacy, loyalty). Next step is to define and focus on the most valuable customer communities. Community management overall has to be more personal. For example, high-standard of customer service in physical retail stores can translate in the equally high standard customer service via WhatsApp, Zoom, and chat.

Community: It’s What Holds Us Together

A brand community jumped quickly from a “nice to have” to a “must have.” It doesn’t matter the category: a brand it has to find a way to put forward its social mission and values, because that’s what holds the community together. For brands that already maintain communities, the next step is to activate it more, and more often. Check out how WFH and Drawn Together (both Marc Jacobs) and GANNI Talks capitalize on the creativity of their brand’s communities. Or, if underwear is your thing, check out the customers willing to share selfies wearing MeUndies products on Instagram. The David Zwirner Gallery recently launched Platform: New York, an online initiative featuring a community of artists from 12 different galleries. TIME Magazine launched TIME for Giving, a community to connect their readers to a list of charities and causes in need.

Again, almost overnight, the importance of community for brands stretched across the sales funnel from end-to-end.  The activation of community is now a top-of-the-funnel tactic (attention, interest), and a long-term, bottom-of-the-funnel strategy (bonding, advocacy, loyalty). Likewise, brands need to define and focus on the most valuable customer communities. Community management overall has to be more personal. For example, top-notch customer service in physical retail stores can be replicated via WhatsApp, Zoom, and chat.

~~~~~~

Content. Across categories, brands have been pivoting to livestream, lifestyle content en masse. Spurred by Instagram Live, every brand these days is in the business of enriching our lives – through recipes, daily meditations, virtual exercises, design hacks to fix our living quarters, life coaching, movie lists, poetry reading, puppy photos, and hobbies. While it may feel overwhelming at times, this lifestyle content pivot is a good thing: it moves the brands away from product marketing and forces them to explore, define, and capitalize on their cultural and social role. During the February lockdown in China, hashtags #StayInFashionGuide and #StayInPajamaContest drew audience of hundreds of thousands. Stay-in style manuals on WeChat, put forward by KOLs, promoted at-home stylish living and solicited “share your look” submissions on Weibo and held #WorkFromHome outfit contests. While situational, these calls to action open up agile content opportunities post-crisis. There’s also a welcome content shift towards live programming and away from polished campaign imagery. Brands are currently asking artist and photographer friends to help them shoot new content from their homes, or asking their community to create something new every week, like Alexander McQueen did with McQueen Creators. Brands will hopefully embrace this lo-fi approach, and put forward scrappy, live, and real content focused on communal watching and socializing. Community-oriented content tends to do better at the moment (versus the polished influencer one), as the currently predominant memes and aesthetic language demonstrate.

Content. It’s King, I Hear.

Across categories, brands continue to pivot to livestream lifestyle content en masse. Largely by Instagram Live, brands seek to enrich our lives — through recipes, daily meditations, virtual exercises, design hacks to fix our living quarters, life coaching, movie lists, poetry reading, puppy photos and hobbies. Yes: it may feel overwhelming at times. Still, this lifestyle content pivot is a good thing: it moves brands away from product marketing and forces them to explore and define (and monetize) their cultural value and social responsibility. During the February lockdown in China, hashtags #StayInFashionGuide and #StayInPajamaContest drew hundreds of thousands of fans. Stay-in-style manuals on WeChat, put forward by KOLs, promoted at-home stylish living. They even solicited “share your look” submissions on Weibo and held #WorkFromHome outfit contests.

While some contests are pandemic specific, these calls to action open up agile content opportunities in the post-vaccine world. There’s also a welcome content shift away from polished campaign imagery towards live programming.
Brands ask artist and photographer friends to help them shoot new content from their homes, or request community members to create something new every week: see the Alexander McQueen Creators. Brands will hopefully embrace this lo-fi approach, and put forward scrappy, live, and real content focused on communal watching and socializing. Community-oriented content tends to do better today. Seen any memes lately?

~~~~~~

Curation. With their marketing budgets on freeze and their campaign content in a distant future, this is a perfect time for brands to embrace the role of curators and bring forth their unique POV on everything from food to film and theater to architecture and pop culture. There has never been a better moment for a trip down the memory lane and for opening up the product archives. Very few brands are doing this (instead, they opt for tiresome PSAs) In contrast, Rihanna, ever my favorite, launched Fenty Social Club on Insta Live with performances and DJ sets. Somewhat far-fetched is the attempt of an Amsterdam hotel to bring the Easter weekend experience into your home, complete with a curated welcome basked mailed in and virtual concierge on call. With a little better to do, indulging in this hospitality-at-distance expert curation is not completely unreasonable. Airbnb is already doing it with its newly launched online experiences. On a more tangible level, fashion retailers can quickly reskin their landing pages to put forward tops suitable for those frequent Zoom calls. Curation plays a key role here: within a retailers’ entire inventory, ask what are the especially Zoom-able items that consumers will gravitate towards? What are the comfortable bottoms to go with them? What is considered a desirable outfit in these days of working from home is new, and retailers can curate the best combos. Discounts have to follow the same curatorial logic that makes sales seem exclusive and special (e.g. “archive sale”), rather than inventory offloading.

Curation. People Like Us Enjoy Things Like This.

With their marketing budgets on freeze and their campaign content in a distant future, brands can to embrace the role of curators and deliver unique POV on food, film and theater, architecture and pop culture and, well, underwear. Since we loathe the present, let’s celebrate the past! Who’s up for a trip down the memory lane (of Madison Avenue)? Open up the product archives. Very few brands are, alas, ready to make this move. (Please stop with the tiresome PSAs. We get it.) In contrast, my beloved Rihanna launched Fenty Social Club on Insta Live with performances and DJ sets, so you can dance along at home, nostalgic for those days when sweating in close proximity with others was not taboo.

More far-fetched is the attempt of an Amsterdam hotel to bring the Easter weekend experience into your home, complete with a curated welcome basket and virtual concierge on call. Still, for those folks with little better to do, indulging in hospitality-at-a-distance expertise is not completely unreasonable. Airbnb is already doing it with its newly launched online experiences. On a more tangible level, fashion retailers can quickly reskin their landing pages to promote tops suitable for Zoom calls. Curation here is key: across your entire inventory, figure out the especially Zoom-able items that consumers will gravitate towards. Also ask: what bottoms go best with these tops? What is considered a desirable outfit in these days of working from home is new, and retailers can curate the best combos. Discounts have to follow the same curatorial logic that makes sales seem exclusive and special (e.g. “archive sale”), rather than offloading old stock..

~~~~~~

Collaborations. The other week, I saw that Supreme collaborated with Lamborghini. While we may be well past the time when a fashion collab can excite anyone, the new breed of collaborations are springing up. They go beyond short-term commercial and PR buzz towards something with a greater social impact and no less buzz. Dairy company Chobani partnered with coffee seller Trade to support the community of independent coffee roasters. The effort is spurred by the common belief of Chobani and Trade that food (and coffee) can be a force for good. In a similar collaborative vein, aperitif company Haus launched The Restaurant Project, where it partnered with a selected group of restaurants across America to co-create nine aperitifs with their chefs. Hundred percent of profits go to the restaurants. Collaborations like these will become new Supreme + X.

Collaborations: The More the Merrier

As you may know, Supreme is not collaborating with Lamborghini. While we may be well past the time when a fashion collab can excite anyone, a new breed of collaborations is popping up everywhere. They go beyond short-term commercial and PR buzz towards something with a greater social impact (and still plenty of buzz). Dairy company Chobani partnered with coffee seller Trade to support the community of independent coffee roasters. The effort is spurred by their belief that food (and coffee) can be a force for good. In a similar collaborative vein, aperitif company Haus launched The Restaurant Project, for which it partnered with a selected group of restaurants across America (and their chefs) to co-create nine aperitifs. One hundred percent of the profits go to the restaurants. Collaborations like these will become new Supreme + X.

~~~~~~

This crisis is not a short-term acute emergency. It is a call to action for companies to pivot and hit a hard reset on the way they do business. The jobs to be done for a brand, going forward, are communal and social, and the business success is defined through how much a company supports other companies, how much it improves lives of their customers, how much good it does to its community, and what kind of society it reflects. Coronavirus won’t kill brands. Complacency will.

The term crisis still makes sense. In the work of branding, though, it’s not a short-term emergency. It’s a call to action for companies to pivot and hit a hard reset on how they do business. Going forward, branding work is communal and social. Business success is defined by how well a company supports other companies, how much it improves lives of their customers, how much good it does to its community, and what kind of society it creates in its image. Coronavirus won’t kill brands. Complacency will.

# # #

And that’s a wrap. If you like what you see, drop me a line over here.

Thanks!

Happy writing!

Lenny’s newsletter: the Cadence edit

Newsletter Challenge, v. 8

Quick note: I recently wrapped up a writing coach arrangement with Ari Lewis, host of the Mastering the Attention Economy podcast. We enjoyed working together (see Ari’s ROI here), and he proposed I take on a newsletter editing challenge.

The challenge: Twenty edits by 22 September.

My primary goal: add clarity, concision, and cadence to the newsletters, and sharpen up my own editing process.

For details on my process, click here, a Google doc. Leave suggestions as you see fit. Thanks!

A Playbook for Fundraising,” Sept 1

@ https://www.lennyrachitsky.com/p/a-playbook-for-fundraising by Marc McCabe (guest writer)

Between the “~~~~~~~~”:

–Grey typeface: Marc.

Normal typeface: me.

Key metrics (original -> edit)
–reading level: 10 -> 8.
–word count: 1831 -> 1630 (12%)
–median sentence length: 22 -> 17 words.
–sentence length, standard deviation (basically, a measure of the variety of sentence lengths): 12.4 -> 12.7.


“Playbook”: the Cadence edit

For an early stage founder, fundraising is one of the most nerve-racking parts of the job. It’s incredibly opaque, asymmetrical, and is often the difference between having a company and not. Even the most experienced founder may have only fundraised 5-10 times in their life, while VCs engage in this process daily.

Nonetheless, it’s also a very exciting time for a founder. Very few people ever get the chance to raise millions of dollars from top tier VCs. As a result, I often see founders rush into the process, setting up investor meetings before they’re truly prepared and end up with a bad outcome. This is a missed opportunity because the fundraising process is a great forcing-function for getting you to think deeply about your business and where it’s going.

For an early stage founder, fundraising is one of the most nerve-racking and exciting parts of the job. It’s incredibly opaque: which part of my message is taking hold? It’s radically asymmetric: you might do this dance five, maybe 10 times across your lifetime. Venture capitalists (VCs) judge these dances on a daily basis. (So, as I note below, practice, practice, practice.) And, it’s often the difference between owning your own company and life as a cog in a machine.

Still, it’s an exciting opportunity — so exciting that founders often rush into the process, meet with investors prematurely and, not surprisingly, end up with a bad outcome. This outcome, too, is bad in multiple ways: you didn’t get funded, of course, but you also missed the opportunity to think deeply about your business and where it’s going.

~~~~~~~~

Over the last decade I have personally helped dozens of companies raise capital, from pre-seed to Series C rounds, and through these experiences I’ve seen a lot of effective, and also counterproductive, fundraising patterns. I shared many of these learnings in a lengthy podcast interview a year ago in, but with a prod from Lenny I felt like now was a good time to revisit this topic.

This guide is for founders of technology businesses who have raised their seed round, and are thinking forward to their next fundraise. It’s most relevant for Series A, but a lot of the same concepts apply for seed rounds, Series B and to a certain extent Series C. While most tech businesses can benefit from this guide, there are plenty of exceptions, especially companies with products which take a long time to get to market, and companies raising capital outside the US. Consider yourself caveated.

Over the last decade, I have helped dozens of companies raise capital, from pre-seed to Series C rounds. So, I’ve seen a lot of effective, well-prepared pitches and, well, other stuff. I I’m delighted Lenny invited me to share a few of those lessons here on his newsletter.

This guide is for founders of technology businesses who have raised their seed round, and are thinking forward to their next fundraise. It’s most relevant for Series A, but most of these ideas apply for seed rounds, Series B and, to a certain extent, Series C. I figure most tech businesses can benefit from my counsel here. Likely exceptions include:

● companies with products which take a long time to get to market, and

● companies raising capital outside the US.

Consider yourself caveated.

~~~~~~

Ultimately, fundraising is an exercise in building trust. Every week we read about new Series A, B and C rounds. We hear about pre-emptive offers and blank check term sheets from prominent investors. All of this can lull us into thinking raising capital is easy. Yet, each partner at a fund generally only makes 1-3 early-stage investments per year, and their career is ultimately staked to how successful these investments are. Each investment is incredibly significant to each fund and in order to convince a fund that you are worthy of that big check, you need them to feel incredibly confident that you will take the money and use it to take your business to a new level, whereby you could raise future funding and ultimately build a huge business. With that in mind, let’s get started with how I like to manage the various steps from thinking about fundraising to closing.

You’re a Builder of Trust, Relationships, and Market Share

Every week we read about new Series A, B and C rounds. We read about pre-emptive offers. And we read about blank-check term sheets from prominent investors. So, raising capital must be easy, right?

No. Understand that each partner at a fund makes one to three early-stage investments per year, and that their career is tied to the success of these investments. So, each investment is a significant component of each fund. In order to convince a VC that your company is a sound investment, you need to persuade them that you (and your company):

● have a great product or service

● will use their money to upscale your business

● will be in a good position for another round of successful funding, and

● will capture real market share.

So, how do you get from first steps to closing?

Let’s think of the four phases of fundraising over the course of a year (yes, a year):

● Preparation

● Outreach

● Navigating the process

● Partner meetings + closing

~~~~~~

Phase 1: Preparation

First, you need to figure out why and when you should raise a round. Maybe this seems obvious, but rather than looking at new investment as an opportunity, many founders only start fundraising when they are running out of money. VC’s don’t invest because you’re running out of money – they invest because they believe their equity stake will be worth a lot more in the future.

When you should raise a Series A round is a blog post unto itself, and I’m not going to go in depth here. The truth is that there isn’t just one factor that will say you’re ready to raise Series A. For example, in SaaS, it’s common that companies that have achieved $1M ARR are told they are ready, but growth rate is a factor as well, and ARR doesn’t always apply for consumer focused businesses.

Tap into your inner Simon Sinek: start with why, then move to when. Seriously: don’t ignore the obvious. Look at a new investment as an opportunity. If you only begin to fundraise when you’re running out of money, you look more like a charity than a business. VC invest because you’ve convinced them that equity purchased today will be worth a lot more in the future.

The matter of when is a big question, and likely a newsletter unto itself. In brief: there isn’t just one factor that indicates you’re ready to raise Series A. In SaaS, companies that have achieved $1M annual recurring revenue (ARR) may be ready, but don’t discount growth rate. ARR isn’t always the best metric for consumer-focused businesses.

~~~~~~

Generally the way to think about whether you are ready for a Series A is whether you’ve proven a credible value hypothesis. This is a combination of factors including the market you’re attacking, the features you’ve built to exploit the opportunity, and how well your product is finding its fit in the market. I often describe Series A as the “Product-Market Fit Round”: You want to show that you’ve convinced a slice of your market that your product is valuable enough to pay for (or if it’s free, use very regularly), and that this user base is growing. While seed rounds are intended to explore an idea and find some fit in the market, raising a Series A helps you pour more fuel on the fire.

Instead, assess the metrics that you’ve confirmed a credible value hypothesis. This hypothesis tests a number of factors, including:

● the market you’re attacking

● the features you’ve built to exploit the opportunity, and

● how well your product fits in this market.

Think of Series A as the “Product-Market Fit Round”: you want to show that you’ve convinced a key market segment that your product is valuable enough to pay for (or, if it’s free, use regularly), and that your user base is growing. While seed rounds are intended to explore an idea and find some fit in the market, raising a Series A helps you sharpen that idea and secure that fit.

~~~~~~~~~

Investors ultimately want to invest in growth. If a company is growing fast relative to its peers, this can make up for lower ARR especially if the business seems defensible and sustainable. It’s often helpful to speak with your seed investors early on about it, especially if they have experience raising capital themselves, to understand what milestones would make most sense to support a new round in the future.

At this point, investors are a key buyer persona, and you need to know their desires. Ultimately, of course, investors desire growth. If a company is growing fast relative to its peers, this can make up for lower ARR, especially if the business seems defensible and sustainable. Talk to your seed investors — especially if they have experience raising capital — about which milestones are most attractive for a successive round of funding.

~~~~~~~

When you think that you’re ready, the first step is to start pulling together your key metrics and wins, such as your growth rates, revenue numbers, customer testimonials, user feedback, and achievements. As mentioned, what makes you ready for Series A varies greatly, so find data points that will get investors excited about your business.

Here are some of the data points that are likely to get investors excited about your business: growth rates, revenue numbers, customer testimonials, user feedback, and achievements.

~~~~~~~

In terms of materials, I advise founders to prepare the following at a minimum:

A short blurb about your business, including a couple of headline numbers that indicate the business is doing well

A short teaser deck (3-7 slides)

A longer presentation deck (12-15 slides)

A 2-3 year forecast with assumed fundraise secured

Optional: Metrics deck or a data room. Sometimes you will get asked for this at Series A, sometimes not. It helps if you ask your prospective VCs in the first meeting whether they’ll ask for it.

You can find some good references for building pitches here, here and here.

Founders should prepare the following materials:

● a short blurb about your business, including a couple of headline numbers that indicate the business is doing well

● a teaser deck (3-7 slides)

● a longer presentation deck (12-15 slides)

● a 2-3 year forecast with assumed fundraise secured

Optional: Metrics deck or a data room. Some VCs will ask for one or the other at Series A. To find out if that’s the case, ask them.

Check out these ideas on how to assemble these materials here, here, and here.

~~~~~~~

The key is that your materials tell a compelling story. They need to explain what you’re building, why you’re building it, and how your strategy will capture considerable revenue in the future. The better this story ties everything together, the more your business will seem insightful. Ultimately we’re all human, and strong narratives that help explain the world around us are more compelling than a selection of disparate, albeit impressive, data points.

Beyond growth, though, investors desire a compelling story. You need to offer a crystal-clear explanation of what you’re building, why you’re building it, and how your strategy will capture considerable revenue in the future. Humans love stories, and a strong narrative will beat a disparate set of data points — no matter how impressive — nearly every time.

“If you can’t tell a credible and compelling story about your vision and how your plans will capitalize on broader societal, market, cultural, economic or other trends, you’re dead in the water. I believe my own secret to fundraising success was that I always spoke to the broader changes I saw happening in the world and my conviction about the opportunities they presented.”

— Eoghan McCabe, co-founder Intercom

As an early investor in Intercom, it always impressed me how consistent the narrative stayed from when the company started up until today.

Eoghan’s a smart guy, and I remain impressed by how consistent Intercom’s narrative has been since the early days.

~~~~~~~

The shorter teaser deck is for sharing over email but be mindful that you don’t want to share everything with VCs ahead of meeting your lead partner. Hence the longer deck for your in-person (or Zoom meetings). Remember, it’s a trust building exercise. In a relationship, trust is built over many interactions over a long period of time. You want to show some positive elements to get investors interested, but leave good content in reserve.

Share the teaser deck over email. The longer deck is for face-to-face or Zoom meetings. Remember, your responsibility is to build trust, which is going to take time, over the course of many interactions. You want to show some positive elements to pique your investors’ interest, but you also want to keep some good content in reserve. We call it a teaser for a reason.

~~~~~~~

One thing that Covid has changed is that building a relationship with a VC, with fewer in-person meetings, is now harder. Think about this with respect to your materials. To make up for the lack of in-person face time, you need to find more digital approaches to building this relationship than before. Caitlin Bolnick recently had an excellent thread about this  so consider preparing some of the following extra materials:

A Loom of your product flow explaining how you made key design decisions and how these relate to the use case or market

An appendix of interesting information you yourself have read or viewed that inspired your approach

A compilation of customer testimonials

Covid makes this part of your job especially difficult. Building a relationship with a VC, with fewer in-person meetings, is tough. Think about this with respect to your materials, and figure how which digital solutions will allow you to seed and grow that trust. Caitlin Bolnick has an excellent thread on this topic, which advises you prepare some of the following extra materials:

● a Loom video of your product flow explaining how you made key design decisions and how these relate to the use case or market

● an appendix of information that inspired your approach

● a compilation of customer testimonials

~~~~~~~

You will need more content than ever to help build a shared belief in what you’re doing and why. I typically recommend spending at least 4 weeks building the deck and supporting materials. I find founders realize there are stronger elements they should have included 1-2 weeks into the pitch process. Taking time to get the narrative right and letting your points crystallize will likely result in a stronger deck from the start.

You will need more content than ever to help build a shared belief in what you’re doing and why. Spend at least four weeks building the deck and supporting materials. In the midst of the pitch process, founders often realize which elements not originally included help them make the best pitch. Take the time to get the narrative right. If you build in the time to let your points crystallize, you will have a stronger pitch deck.

~~~~~~~

An important component in building this content is a part of the process I like to call “Hardening the Pitch”. Typically I recommend founders prepare their materials to about 70% completeness and then test them before going into battle. Put together a coherent story with great supporting data (not necessarily heavily designed). Find 4-6 people in your network, who have either fundraised at Series A for their own startup (ideally in the same or similar space), are friendly investors who know the space (perhaps from your seed investors), or even growth stage investors. Practice your pitch with them. Testing your materials and thesis before you hit the full pitch gauntlet will build your confidence and reps on the pitch. It will also provide you with helpful feedback and, potentially, warm introductions to relevant funds. I’ve seen this be immensely helpful in securing strong investment leads.

Batter Up: Get on the Mound and Pitch

You’re a pitcher and, in this stage, you get to “Harden the Pitch.” I recommend founders prepare their materials to about 70% completeness and then test them with live hitters. Put together a coherent story with great supporting data and some modest design elements. Find 4-6 people in your network who have either fundraised at Series A for their own startup (ideally in the same or similar space), are friendly investors who know the space (perhaps from your seed investors), or even growth stage investors. Practice your pitch. Fine tune your content and your delivery. The more reps you take, the greater your confidence. Plus, it’s not just the feedback: it may result in warm introductions to relevant funds. And warm leads can be immensely helpful.

~~~~~~~

“Fundraising can be a lonely experience, especially as you will want to protect those in the company from the highs and lows during your round. Finding some good external people to lean on for vetting your pitch or providing introductions can really help relieve some of the burden on founders.”

— Jonathan Golden, NEA

I generally think you should plan to spend somewhere between 8-16 weeks working on your fundraise from start to term-sheet. You’ll be ideally speaking to 50-60 funds for your Series A. Starting early in the year makes sense, but if you’re in July and contemplating raising, it might make sense to wait for late August or early September to begin your outreach to funds. There are a lot of great jokes I could share about VC vacations in August, but the truth is that plenty of VCs work through August. Just maybe not enough to run a tight process with every fund.

Plan to spend eight to 16 weeks working on your fundraise from start to term-sheet. You should speak to 50-60 funds for your Series A. Start early in the year. If it’s summertime, though, you may want to wait until late August or early September to begin your outreach. VCs, like therapists, often vacation in August.

~~~~~~~

Another factor to consider when you go out to raise is runway. Generally I recommend having at least 8 months of runway when going out to raise. The most important thing is that your business is showing the signs that you should raise Series A. If you only have 4-6 months of runway, it might make sense to raise a bridge round from inside investors to gain leverage in the fundraising process. You will want to continue to show traction during the fundraising process as often investors ask for updated numbers as you get close to the end and a downturn can shake their confidence. It’s really helpful to think about fundraising at least 12 months before you need it so you can time things well. I pulled together a quick fundraising calendar below to help you think about the overall timing of the different elements of your round.

Consider, too, the length of your runway: I recommend no fewer than eight months for a Series A runway, and only if your business is showing the signs noted above. If you only have four to six months of runway, consider a bridge round with inside investors to gain leverage in the fundraising process. Be prepared to show traction during the fundraising process, too. Investors often ask for updated numbers as you get close to the end, and a downturn can shake their confidence. Ideally, you’re thinking about fundraising at least 12 months before you need it, in order to optimize the timing of each phase. Check out the fundraising calendar below, which outlines the overall timing of the different elements of your round.

https://cdn.substack.com/image/fetch/f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fbucketeer-e05bbc84-baa3-437e-9518-adb32be77984.s3.amazonaws.com%2Fpublic%2Fimages%2F9c45e391-60ea-4a07-949e-5e909cd28a18_1600x621.png

# # #


And that’s a wrap. If you like what you see, drop me a line over here.

Thanks!

Happy writing!

The Maybe Baby newsletter: the Cadence edit

Newsletter Challenge, v. 7

Quick note: I recently wrapped up a writing coach arrangement with Ari Lewis, host of the Mastering the Attention Economy podcast. We enjoyed working together (see Ari’s ROI here), and he proposed I take on a newsletter editing challenge.

The challenge: Twenty edits by 22 September.

My primary goal: add clarity, concision, and cadence to the newsletters, and sharpen up my own method.

For details on my process, click here, a Google doc. Leave suggestions as you see fit. Thanks!

“Who are you online?,” Aug 23

@ https://haleynahman.substack.com/p/20-who-are-you-online, by Haley Nahman

Between the “~~~~~~~~”:

–Grey typeface: Haley.

Normal typeface: me.

Key metrics (original -> edit)
–reading level: 8 -> 7.
–median sentence length: 17 -> 14 words.
–sentence length, standard deviation (basically, a measure of the variety of sentence lengths): 11 -> 11.


“Who are you … “: the Cadence edit

August 23, 2020

Why hello,

Today marks my 20th Maybe Baby newsletter. That feels like nothing and also something! For my 21st I promise to get drunk. Today I’m writing about who we are online, and the difference between habitual deleters and those who let it all hang out. Which are you? Let me know in the comments. Also please enjoy some of my old Instagrams, sprinkled throughout for posterity and starting with the first selfie I ever posted:

C’mere weekendddd!!!

Why hello,

Today marks my 20th Maybe Baby newsletter. That feels like nothing and also something! For my 21st I promise to get drunk. Today I’m writing about who we are online, and the difference between habitual curators and folks who let it all hang out.

Which one are you? Let me know in the comments.

Also please enjoy some of my old Instagrams, sprinkled throughout for posterity and starting with the first selfie I ever posted …

~~~~~~~

Pulling levers

I’ve gotten into the bad habit of deleting Instagram Stories after I post them. Three from recent memory: A flash of me lifting my shirt up to reveal a ridiculous banana bikini. A video of me dancing alone in my apartment to a pop song, muted and scored with classical music to make me look like someone who died 50 years ago. A series of memes wherein I overlaid photos of animals with text that indicated I hated the internet. All equally stupid. None remotely useful. Delete delete delete!

I’ve recently developed the habit of deleting my Instagram Stories, including:  

–me lifting my shirt up to reveal a ridiculous banana bikini

–me dancing alone in my apartment to a pop song, muted and scored with classical music, and

–a series of memes wherein I overlaid photos of animals with text that indicated I hated the internet.

All equally stupid. None remotely useful. Delete delete delete!

~~~~~~~

I never used to do this. I’ve historically seen deleting as a kind of failure—at being authentic, maybe, or at least being consistent enough to not renege on a decision you’ve ostensibly made of sound mind. I’ve only ever archived three Instagram photos from my feed because I felt they were misunderstood. I’m pretty sure this places me squarely in the millennial generation, known to hoard our internet output as if it were a time capsule, compared to our younger counterparts, known for whittling their accounts down to only the most relevant information. One of my distant cousins only ever has between 10 and 20 photos on her Instagram feed, which change regularly. I’m sure the real shit is elsewhere, hidden from nosy people like me. My feed, meanwhile, has 1,216 posts dating back to 2011.

I never used to do this. I’ve long regarded deleting as a failure of authenticity, maybe, or a failure to honor a decision you’ve ostensibly made of sound mind. I’ve only ever archived three — yes, three — Instagram photos from my feed because the feedback indicated they were misunderstood. This ethos places me squarely among the millennials of Gen Y, which hoards its internet output as if it were a time capsule, rather than Gen Z, which whittles their accounts down to the most relevant information. One of my distant cousins maintains 10 to 20 photos on her Instagram feed, and they change regularly. I figure the real shit is elsewhere, hidden from nosy people like me. My feed, meanwhile, has 1,216 posts dating back to 2011.

~~~~~~~

A few eras of my internet life are gone. My old Myspace account, decorated with embarrassing photoshops; an old Tumblr I panic-deleted when I was 19. But most of it is out there—old blogs, try-hard posts, bad writing—even if I’d never willingly guide someone to it. Something about this feels right to me. As if by refusing to hide my former self I am standing by my right to publicly evolve, and by extension am preserving the right for others. Or at least that’s what I tell myself. On a creative level, I love reading undercooked writing from writers I now think are brilliant. It gives me hope to bear witness to the arc, rather than just hear about it once it’s been mythologized in an interview about The Creative Process. Real canon is more inspiring, and I appreciate people brave enough to leave their early work up. Not sure it makes sense to apply this moral framework to my “work” from 2012, but that’s what I’ve done.

Still, a few eras of my internet life are gone. The two big ones include my Myspace account, decorated with embarrassing photoshops, and a Tumblr account I had when I was 19 and panic deleted. Otherwise, it’s out there: old blogs, try-hard posts, bad writing—the kinda stuff I’d never willingly guide someone to. Something about this feels right to me. By refusing to hide my former self, I stand by my right to publicly evolve and, by extension, preserve that right for others, too. Or at least that’s what I tell myself. On a creative level, I love reading the early, undercooked work of writers I now consider brilliant.

Rather than hear about how the writer represents that arc in The Creative Process, I want to bear witness to the arc. The Real Canon is a source of inspiration. I really appreciate people brave enough to leave their early work up. Not sure it makes sense to apply this moral framework to my “work” from 2012, but it’s right there where I left it.

~~~~~~~

Thus, my rule has been: don’t delete. Live with our stupid internet choices like we live with any choice we’ve made in our lives, whether it’s an outfit we wore or a thing we said or a place we went. So maybe we wouldn’t do the same thing now, but that’s just how life works, doesn’t it? Shouldn’t we be allowed to disagree with our former selves? In fact, wouldn’t it be an issue if we didn’t?

My rule, then: don’t delete. Let’s live with our stupid internet choices like we other choices, from an embarrassing outfit, a too-aggressive comment or a place we used to go. So maybe we wouldn’t do the same thing now, but that’s just how life works, doesn’t it? Shouldn’t we be allowed to disagree with our former selves? In fact, wouldn’t it be an issue if we didn’t?

~~~~~~~

The problem with thinking this way is it implies a stronger parallel between online and offline life than actually exists. No matter how stubborn I am about “embracing the arc,” I can’t deny that the internet registers as far more flat. We may be able to understand, intellectually, that a stupid joke was posted 10 years ago, when “Tik Tok” was a #1 song and everyone was blowing their load for Avatar—the timestamp says as much. But on Twitter the joke is clear as day, next to the person’s current photo and handle as if it were said just now. It feels current. In real life our memories can’t recall 10-year-old offhand comments with such clarity—we’ve forgotten or overwritten the information with new context and data. We understand that a lot of time has passed because we lived through it. Online those barriers don’t exist; your identity is divorced from linear time. It is a readily available mosaic of everything you’ve ever done.

There’s one problem with this way of thinking: it depends upon a stronger parallel between our lives online and offline than actually exists. No matter how stubborn I am about “embracing the arc,” I can’t deny that, on the internet, that arc appears far more flat. We may be able to understand, intellectually, that a stupid joke was posted 10 years ago, when “Tik Tok” was a #1 song and everyone was blowing their load for Avatar—the timestamp says as much. But on Twitter, that decade-old joke appears next to your current photo and handle, as if today’s you said it just now. It feels current. In real life, we can’t recall 10-year-old offhand comments with such clarity—we’ve forgotten that stuff, and mercifully so. We understand that time has passed because we lived through it. Your online identity is divorced from linear time. You are a readily assembled mosaic of everything you’ve ever done.

~~~~~~~

Maybe, then, Gen-Z—or however you’d define the now-cross-generational population of people who hyper-curate their feeds—has it right. The way they approach content is in better harmony with how it’s interpreted: as an upload of who you are, timestamp-agnostic. Why not delete everything you don’t currently stand by if that’s how it will be understood by others? Obviously this is the appeal of Snapchat and Instagram Stories; they self-destruct, thus saving you the trouble. The journalist and prolific tweeter Elizabeth Bruenig has a bot that deletes all her tweets after two weeks. When I first heard that, the digital hoarder in me was horrified. Didn’t she want a record of what she’d said, conversations she’d had, articles she’d posted? But the more I thought about it, the more I got it. The trend of disappearing content is a response to the fact that the internet is functionally similar to a printing press, providing ideas with a permanent home, while being used more like a casual, everyday forum. The utility and its medium are incongruent, and manufactured ephemerality is trying to address that.

Maybe, then, the hyper-curators of Gen-Z have it right. Gen-Zers regard their content in a much more harmonious way with how it’s interpreted: as an upload of who you are, timestamp-agnostic, since that’s how you’re bound to be understood by others. Hence the appeal of Snapchat and Instagram Stories: they self-destruct, and save you the trouble. The super-tweeting journalist Elizabeth Bruenig has a bot that deletes all her tweets after two weeks. When I first heard this story, the digital hoarder in me was horrified. Didn’t she want a record of her comments, her conversations, and the articles she posted? But the more I think about it, the more I get it. The trend of disappearing content is a response to the fact that the internet is functionally similar to a self-archiving printing press. It typesets ideas and provides them with a permanent home.  It’s primary use, though, is like the table of communal magazines at a coffee shop, where things are regularly tossed into the dustbin of history, as they say. The medium and its utility are incongruent, and the trend toward manufactured ephemerality is a logical way to address that.

~~~~~~~

Still, I resist it. I don’t want everything online to self-destruct. I don’t like that the most impulsive content is now gone in 24 hours, and I resent that this has imbued anything posted to the feed with an air of importance—or more accurately, performance. I’ve never really wanted my internet presence to “represent” me like a one-sheeter on who I am. I find that stressful. As an increasing number of my followers are strangers to me, it’s made me more aware of the gap that exists between who I am online—much softer, less goofy, more careful—than I am offline. It’s as if I’m a muted version of myself in 2D, so self-conscious and censored. That’s the insecurity that drove me to post those three stories I ended up deleting; I hoped they might show a looser side of me, and then I became certain, ironically, that they felt forced. There are some things we simply can’t transmit digitally—how we behave in conversation, how much we roll our eyes, the way our faces move, how we dance in a crowd. All the visceral information that fills out a person.

Still, I resist it. I don’t want everything online to self-destruct. I don’t like that the most impulsive content is now gone in 24 hours, and I resent that this trend has imbued anything posted to my feed with an air of importance—or, more accurately, performance. I never wanted my internet presence to “represent” me like a one-sheeter. That’s too stressful. An increasing percentage of my followers are bound to be strangers, and that fact’s made me more aware of the gap that exists between who I am online—much softer, less goofy, more careful—and who I am offline. It’s as if I’m a muted version of myself in 2D, self-conscious and self-censoring. That insecurity drove me to post the three stories I ended up deleting. I wanted those posts to show a looser side of me and, once I saw them online, I became certain, alas, that they felt forced.

There are some things we simply can’t transmit digitally.

How we behave in conversation, and the way we roll our eyes.

The way our faces move, and the way we dance in a crowd.

All the visceral information — nay, the viscera itself. Our flesh. Our blood. What it feels like when we touch.

~~~~~~~

Our accounts are meant to reflect us, but posting is an entirely different form of expression, bringing out different sides of different people. In some ways you can do so much more to express yourself online than you can in person, and in others ways, so much less. And as much as we’re aware of the gap that exists within ourselves, it’s easy to forget to appreciate it in others. It’s the digital equivalent of: “We judge ourselves by our intentions and others by their behavior.” I know that you can’t really understand me based on my Instagram, we might think, but I completely understand you based on yours. I’m sure my increasing focus on this has come with developing a following, but I also think it’s increased for everyone as the venn diagram of “presumed identity” and “online presence” has moved closer to a circle. And especially as the stakes of who we are online have been raised by our inability to interact in person.

Our accounts reflect who we are, but in a fun mirror sorta way. Posting is a form of expression unto itself, and it brings out different sides of different people. In some ways you can do so much more to express yourself online than you can in person. In other ways, it’s so much less. And as much as we’re aware of the gap that exists within ourselves, it’s easy to forget to recognize that gap with others. It’s the digital equivalent of: “We judge ourselves by our intentions and others by their behavior.” I know that you can’t really understand me based on my Instagram, but I’m certain I completely understand you based on yours. I’m sure my increased focus on this has come with developing a following, but I also think it’s increased for everyone. The Venn diagram categories of “presumed identity” and “online presence” appears to be nearly a unified circle. And, our inability to interact in person, to remind others of our visceral selves, has raised the stakes of curating our online personae.

~~~~~~~

In this way I guess I don’t really disagree with hyper-curators; we’re merely responding to the same insufficiency in different ways. I’d imagine most people don’t really want to be summed up by their shitposts. If the original promise of the internet was to connect us to more people, the challenge now is to remember it can only do that to an extent, or through a very particular type of lens. I’ll never forget interviewing a communication scholar years ago who told me that humans evolved to communicate and cooperate in person using not just words, but tone, context, and body language. She explained that when phones were invented, there was a barrier to understanding because facial expressions were lost, and when email became a primary mode of connection, tone was lost, and when talking to strangers online became the status quo, context was lost. Our tools have evolved faster than our biology. In other words, we are not ready. (Weird, because honestly things seem to be working out!)

So, I suppose I actually agree with the hyper-curators. We’re merely responding in different ways to the gap between the real and the representation. I imagine most people don’t really want to be summed up by their shitposts. If the original promise of the internet was to connect us to more people, the challenge now is to understand the limits of those connections, or to recognize how the impact of a particular lens on those connections. . I’ll never forget interviewing a communication scholar years ago who told me that humans evolved to communicate and cooperate in person using not just words, but tone, context, and body language. She explained that when phones were invented, there was a barrier to understanding was built in, because facial expressions were lost. When email became a primary mode of connection, that barrier shifted, as tone, volume, and timbre were lost. When talking to strangers online via new video platforms, the old barriers were reduced, but context was lost. Our tools have evolved faster than our biology and raises a key question for pandemic times: how ready are we, for any of this? (Part of me thinks, yeah, sure, as things seem to be working out. Another part of me, well … )

~~~~~~~

Anyway, it’s easy to shrug off social media anxiety as silly, or to assume that worrying about how we’re coming off online makes us vapid—and there is something undeniably narcissistic about it—but social belonging is at the center of society, and has been since the beginning of it. Humans fear ostracism more than death. Whether we’re extremely online or not, we’re making a choice about how we participate in modern life that has real social implications. The pandemic has of course brought this into sharper relief, with our sloppy way of digital cooperation bringing about meaningful political movements as much as mass conflict. I’m still convinced we’d all fight way less in real life. The question is how do we adapt to the fact that the internet isn’t a digital reflection of the physical world but a paradigm shift away from it? I don’t think my hope that we’ll start giving each other the benefit of the doubt is remotely realistic (lol), nor do I find it existentially satisfying to edit ourselves into oblivion. What do you think is the solution?

It will be fascinating to see how the internet evolves, and a miracle if it even manages to before we light the whole thing on fire. Anyone’s guess as to which comes first.

Anyway, it’s easy to shrug off social media anxiety as silly, or to assume that worrying about how we present ourselves online makes us vapid. Sure, there is something undeniably narcissistic about it. And yet: we crave belonging We’re social creatures, with IRL needs. Humans fear ostracism more than death. (It’s scientifically confirmed here. For most species, ostracism is social death.) Whether we’re fully digital or mostly analog, we choose how we participate in modern life, and that choice has real social implications. The pandemic has of course brought this into sharper relief, with our sloppy modes of digital cooperation producing meaningful political movements as well as mass conflict. I’m still convinced we’d all fight way less in real life. (Anyone can pick a fight on Twitter.)

For me, here’s the key question: how do we respond to the fact that the internet isn’t a digital reflection of the physical world but a paradigm shift away from it? Can you imagine that it’s remotely (lol) realistic to hope that we’ll drum up the generosity to see “the Real Canon” online and give each other the benefit of the doubt? And, if not, is it either sustainable or existentially satisfying to repeatedly edit ourselves into oblivion?

What do you think is the solution?

It will be fascinating to see how the internet and humans co-evolve. It may be a miracle if web 3.0 emerges before we light the whole thing on fire. Which comes first is anyone’s guess.

# # #

And that’s a wrap. If you like what you see, drop me a line over here.

Thanks!

Happy writing!

Dave Nemetz Rises: the Cadence edit

The man behind Bleacher Report and Inverse returns.

Newsletter Challenge, v. 6

Quick note: I recently wrapped up a writing coach arrangement with Ari Lewis, host of the Mastering the Attention Economy podcast. We enjoyed working together (see Ari’s ROI here), and he proposed I take on a newsletter editing challenge.

The challenge: Twenty edits by 22 September. In paired blocks below, you’ll find the original and my edit, separated by a “~~~~~~.”

My primary goal: it’s typically simple: “add clarity, concision, and cadence.” Mr. N.’s essay poses a different challenge. Check my note at the end.

For details on my process, click here, a Google doc. Leave suggestions as you see fit. Thanks!

“Making things and putting them on the internet,” Sept 2

@ https://davenemetz.com/making-things-and-putting-them-on-the-internet/, by Dave Nemetz

Regular face: Dave.

Bold face: me.

Key metrics here: not really useful, since the essay was already at a reading level of 5. (My edit is grade level 4, in case you’re curious, but I’m after the question of voice here — see my note at the end.)


Making things …”: the Cadence edit

August 4, 2020

Last year, a friend who runs a middle school in Red Hook, Brooklyn invited me to speak to a group of eighth graders at their career day. My fellow speakers were an education administrator and a pharmaceutical salesperson. Compared to them, my career arc was a little harder to explain.

My message boiled down to this: I had built a career off of making things and putting them on the internet.

A dear friend of mine runs a middle school in Red Hook, Brooklyn and, last October, invited me to speak to a group of eighth graders on career day. My fellow speakers included an education administrator and a pharmaceutical salesperson. They both provided a clear sense of what they do at work. For me, that wasn’t quite so easy, especially when it came to explaining how I made it to this point of adulthood.

My message boiled down to this: I made things, I put them on the internet, and people really, really liked them.

~~~~~~

If it weren’t for the pandemic, class would be in session.

I started with an idea: a sports website called Bleacher Report that my friends and I had dreamed up. We didn’t feel like there was a sports site out there that covered the teams we cared about, or talked about sports the way we did with our friends.

So we built it. We put it on the internet. People liked it. We kept improving on it. Kept creating and building. Rinse and repeat, that’s been my career.

I wasn’t telling these kids to go post everything they did or thought they had to the internet. In today’s era of oversharing and social media anxiety, that sounds irresponsible. I may have even seen the teacher wince as I started to go down that path.

Most things start with ideas — or dreams, really. Years ago, my friends and I dreamed up a sports website called Bleacher Report. The bleachers, as you probably know, are the cheapest seats at a stadium, and they’re often filled with the most devoted fans. We started Bleacher Report because we believed the world needed a sports site that covered the teams we cared about. And talked about sports the way we talked about sports with our friends.

So we built it. We put it on the internet. People liked it. We kept improving it. Create, build, improve. Rinse and repeat. That’s my career model.

Now, I didn’t tell these kids to go post everything they did or thought onto the internet. In today’s era of oversharing and social media anxiety, that would be irresponsible. I even saw the teacher wince, as she seemed to think I was headed down that path.

~~~~~~

My message was more about trusting the creative process. Not being afraid to think of something new. To create and put it out there for the world to see. To share your ideas and dreams with others. To seek feedback and collaborators. If you have the courage and conviction to do that, good things can happen.

Being creative means being vulnerable and avoiding self censorship. Do that, and you can open up new pathways and possibilities. I never would have imagined that the sports website I started with friends in my early 20’s would one day rival ESPN. And yet here we are.

I’ve built my whole career on making things and putting them on the internet.

My message was reckless, but in a different way: trust the creative process. Think of something new, and don’t be afraid it. Make it real. Put it out there for the world to see. Share your dreams with others. Seek feedback and be grateful. Find collaborators. If you have the courage and conviction to do that, good things can happen.

Being creative means being vulnerable. You will have impulses of self-censorship. Accept them when they sneak into your brain, and gradually show them the door. Now open up new pathways and possibilities. I never would have imagined that the sports website I started with friends in my early 20’s would one day rival ESPN. Yet here we are.

I’ve built my whole career on making things and putting them on the internet.

~~~~~~

First there was Bleacher Report. Then inspiration struck again. I had an idea for a site that covered science and innovation alongside science fiction and comic books. So I created Inverse. Within each of these larger projects there have been countless smaller components of creation.

There’s no greater adrenaline shot for me than creating. The process of forming an idea, building on it, and bringing it to life never fails to get me into a flow state. Every startup or creative pursuit provides boundless opportunity for this process. That’s where the fun is.

The internet is the perfect medium to engender this process. You can think of something, and instantaneously put it out there for all the world to see. Others can find it, and build on it. It’s magic.

After Bleacher Report, inspiration struck again. I wanted a site that covered science and innovation alongside science fiction and comic books. So I created Inverse. Within these two big projects, we created countless, smaller components of value for our audience.

I love a good shot of adrenaline, and there’s no greater adrenaline boost for me than creating. The process of forming an idea, building on it, and bringing it to life delivers me into a state of flow. You know that state: it’s what dreams are made of. Every startup or creative pursuit provides boundless opportunity to get back in that space. That’s where the fun is.

The internet is the perfect medium for this stuff. You think, you build, and you put it out there for all the world to see. Others find it, and they build on it. It’s magic.

~~~~~~

Over the course of building two companies, I found less time for being creative. Many of my days filled up with managerial and operational responsibilities. Those parts of building businesses are essential, especially as you scale. But for me, nothing beats the spark of creativity.

Recently, I’ve been re-evaluating how I spend my time and mental energy. After selling Inverse last year, the thought of “What’s next?” has become more front and center. And spending more time at home these last few months has led to more moments of introspection.

We all have the choice of what we focus on, what activities we make time for in our lives. As I’ve pondered that decision, the path for me has become clear. It’s led me back to the one thing that has been a through line my entire adult life.

I’m excited to go back to the beginning. To making things and putting them on the internet.

In the course of building two companies, I couldn’t avoid the growing list of managerial and operational responsibilities. Those parts of building businesses are essential, especially as you scale. But for me, nothing beats the spark and the rush of creativity.

Recently, I’ve been thinking again about how I spend my time and my mental energy. After selling Inverse last year, one question loomed: “What’s next?” And spending more time at home these last few months has given me plenty of time to answer that question.

We all have the choice of what we focus on, what activities we make time for in our lives. For me, again, that path is clear. It’s led me back to the one thing that has been a through line my entire adult life.

I’m excited to go back to the beginning. Again. To make things, put them on the internet and, best of all, to see what you do with them.

# # #

Note: Dave’s essay posed a real challenge, a fun challenge, really, since it is distinctively autobiographical.

Folks like my friend @arilewis might call Dave’s style “authentic.” It’s from the heart. It’s easy to connect with. It inspires you to call Dave and ask him to share a beer with you over Zoom. (I don’t know Dave, so I don’t know what weird things he does on Zoom.)

An anecdote: Years ago, while riding in the car with a mentor of mine in Orange County, CA, we started talking tacos, and I mentioned my devotion to El Gallo Giro, in Santa Ana. “The best I’ve found,” I said. “Totally authentic.”

“Authentic?,” he chortled. “What does that even mean?” He asked if I could imagine Italian food without tomatoes. “Of course not,” I blurted. Then he reminded me that tomatoes are a New World food. He went silent, and let me draw my own conclusion: so, is every red sauce a fake? Of course not.

The tomato is not the problem. The esteem we give authenticity is the problem. It was a great lesson to learn, one that is useful to recall in discussions of cultural appropriation: nothing is innocent (or pure or authentic). Everything is hybrid. (Is there theft? Sure, but that’s a different question.)

So it’s important for talking about food, music, art … so why not writing? What does it mean to be “keeping it real”? How is writing hybrid, a mix of a personal voice and stylistic variations? (Let’s imagine a voice can be personal — rather than completely social.)

I do believe in stylistic mastery, and Dave’s got a brilliant sense of style. It’s conversational, of course, and deceptively simple. It takes work to master any style. My changes here aim to give his work a slight boost in that regard.

For example:

Dave: “Last year, a friend who runs a middle school in Red Hook, Brooklyn invited me to speak to a group of eighth graders at their career day.” For the lead, I made it a dear friend (more familiar) and pegged the date to October (more specific). If Dave’s friend reads this and is surprised to learn Dave considers them a dear friend, no harm done.

Dave: “My message boiled down to this: I had built a career off of making things and putting them on the internet.” I love a good power trio. Jimi Hendrix in 1967. Duke and Max and Mingus. And I love a list with three things, too. So, I elaborated that line into,

My message boiled down to this: I made things, I put them on the internet, and people really, really liked them.

I was first tempted to say something about money, but Dave steers clear of any mention of money. (It defies the unwritten rules of this style of voice.) Since Dave — like all writers — is writing for an audience, it’s useful for him to regard them here and, of course, now he’s all set up for the coda.

Part of this style, too, entails a willingness to explain. Dave uses no insider acronyms here, so I took that a step farther to explain the likely inspiration for the name “Bleacher Report” to the non-baseball fans. (Serious question: are there bleacher seats in other sports?)

Dave: “After selling Inverse last year, the thought of “What’s next?” has become more front and center.” This question is a big one — big enough that it should come with the emphasis that’s only available at the end of the sentence.

After selling Inverse last year, one question loomed: ‘What’s next?’”

I hope that gives you a sense of why “authentic” might not be the best adjective here. How could any editor make Dave’s voice more authentic?

I’d like to imagine I recognized the parameters of Dave’s style and nudged it forward a bit.

And that’s a wrap. If you like what you see, drop me a line over here.

Thanks!

Happy writing!