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10 years of professional blogging – what I’ve learned

Building your personal bat signal
I want to cross-pollinate a tweetstorm on lessons I’ve learned from a decade of professional writing. In a way, it’s a followup to some more general life lessons from 10 years of living in the Bay Area. Writing has been enormously impactful from a professional standpoint, and I continue to recommend to everyone – especially folks who are new to the Bay Area – to do it as a way to send out the “bat signal” on their aspirations, ideas, and interests.

It’s awesome, but insanely hard to get started. Of course, everyone knows the mechanics of setting up a blog – but the hard part is finding your voice, figuring out topics that are interesting for other folks to read, and building a long-term habit.

The lessons
Without further ado, here are a few opinions I’ve developed up along the way:

  • Titles are 80% of the work, but you write it as the very last thing. It has to be a compelling opinion or important learning
  • There’s always room for high-quality thoughts/opinions. Venn diagram of people w/ knowledge and those we can communicate is tiny
  • Writing is the most scalable professional networking activity – stay home, don’t go to events/conferences, and just put ideas down
  • Think of your writing on the same timescale as your career. Write on a multi-decade timeframe. This means, don’t just pub on Quora/Medium
  • Focus on writing freq over anything else. Schedule it. Don’t worry about building an immediate audience. Focus on the intrinsic.
  • To develop the habit, put a calendar reminder each Sunday for 2 hours. Forced myself to stare at a blank text box and put something down
  • Most of my writing comes from talking/reading deciding I strongly agree or disagree. These opinions become titles. Titles become essays.
  • People are often obsessed with needing to write original ideas. Forget it. You’re a journalist with a day job in the tech industry
  • An email subscriber is worth 100x twitter or LinkedIn followers or whatever other stuff is out there. An email = a real channel
  • I started writing while working at a VC. They asked, “Why give away ideas? That’s your edge.” Ironic that VCs blog/tweet all day now ;)
  • Publishing ideas, learnings, opinions, for years & years is a great way to give. And you’ll figure out how to capture value later

But let’s talk about each one of these in more detail.

The lessons, but with more detail!

Titles are 80% of the work, but you write it as the very last thing. It has to be an compelling opinion or important learning

Titles are often written as a vague pre-thought, but in fact, it’s the most important creative decision you’ll make. Titles are the text that’ll be featured prominently in every tweet, Facebook share, and link – and people will refer to it by name. Titles are best when they can pass the “naked share” test – imagine some text that’s so compelling that even if it’s not linked to anything, people will want to share it.

The best example of this in my work is “Growth Hacker is the new VP Marketing” which started out as a tweet with 20+ shares, and then was developed into an essay afterward. To pass the naked share test, this means a title should be an opinion on its own. Or be a factoid (like push notifs being 40%+ CTR) that’s fascinating and shareable. Or if that’s just too hard, the common “curiosity gap” pattern of a listicle can work too. Just avoid vague titles like “Here are my thoughts on XYZ.” No one cares. As a result, in the course of my work, I often write a placeholder title, write the essay, and then at the very end, spend a good chunk of time iterating on titles until there’s a good one.

There’s always room for high-quality thoughts/opinions. Venn diagram of people w/ knowledge and those we can communicate is tiny

You might think that there are too many blogs on tech, startups, whatever. There’s always room though, when you think of the whitespace as Knowledge x Communication x Medium. People with real knowledge are busy, especially when that knowledge is under a huge amount of demand. And even when an expert can poke their heads up and do something besides executing their craft, they often can’t communicate! It’s hard to make professional content – often dry, boring, technical – into something that’s compelling and accessible to a wide audience. And furthermore, I’d add the medium into the mix as a third dimension, which is the idea that the knowledge can be shared via video, long-form essays, podcasts, presentation decks, etc. Even when there are experts writing long-form content about cryptocurrencies, let’s say, there’s still room in the market for a highly visual version. Just figure out the whitespace and dive in!

Writing is the most scalable professional networking activity – stay home, don’t go to events/conferences, and just put ideas down

When I first moved to the Bay Area, I was spending at least one afternoon/evening a week at a launch party, a conference. Plus hours and hours of 1:1s as I was meeting a ton of people. After an entire year of hard work, I had met something like 1000 new people for one-off conversations. But it took hundreds of hours. At the same time, I was dedicating about the same amount of time to writing, but quickly unlocked 5,000+ people, and started reaching into their inboxes on a weekly basis.

Speaking at conferences is the worst time suck. You spend hours prepping a deck, speak to a group of perhaps a few hundred people, and retain very few them in any meaningful relationship. It can feel good to be recognized, but at the same time, it just can’t compare to writing a piece of content that lives forever. I’m still getting traffic – and email feedback – on essays I wrote ten years ago, which is insane! But that’s the power of scale – nothing can beat content as a bat signal.

Think of your writing on the same timescale as your career. Write on a multi-decade timeframe. This means, don’t just pub on Quora/Medium

Building your network, your audience, and your ideas will be something you’ll want to do over your entire career. Likely a multi-decade thing that will last longer than any individual publishing startup. That’s why I refuse to write on Medium or Quora. Instead, I prefer to run open source software that I can move around, prioritize building my email list (more on that later) and try to keep regular backups. I used to write on Blogger and watched them slowly stop maintaining the platform after the Google acquisition. Then I switched to Typepad, only to watch the same thing happen. I learned my lesson.

Focus on writing freq over anything else. Schedule it. Don’t worry about building an immediate audience. Focus on the intrinsic.

I get it- the activation energy to start publishing your professional ideas and thoughts are high. Nevertheless, because initially no one will read your work, the key is just to get started. Your initial topics and format should be whatever you can do easily and maintain some sort of frequency. Maybe that’s 500 words a month on a new product you’ve tried, and whether you hate or it not. Just get started, find out what you like, and you’ll have a lot of time to figure out the intersection of what you want to write, and what others want to read.

To develop the habit, put a calendar reminder each Sunday for 2 hours. Forced myself to stare at a blank text box and put something down

Several years in, writing remains hard. It’s something that still – to this day – requires time to be set aside. I turn off the music, stop checking email, and write over a few hours to crank something out. Some parts get easier, but the core activity stays difficult. Since starting a normal job (haha) it’s gotten harder to write on Sunday evenings, since that’s when the work email starts. But a good chunk of the writing on this blog happened over Sunday evenings, a few times a month, blocked out with no distractions.

Most of my writing comes from talking/reading deciding I strongly agree or disagree. These opinions become titles. Titles become essays.

After a lively lunch/dinner discussion where a provocative opinion is blurted out – say, that cryptocurrencies are going to be widely adopted and ultimately cause a global recession – I usually write it down. If it’s fun and memorable, it’s an easy thing to write 3-4 supporting points as paragraphs, and turn into an essay later.

People are often obsessed with needing to write original ideas. Forget it. You’re a journalist with a day job in the tech industry

Thinking of yourself as a journalist that’s covering interesting ideas, trends, products, and everything that’s happening around you leads to much better/stronger content. It means you can write often and build on others’ ideas, without feeling like everything has to be completely new. Just as startup ideas are rarely new, but rather twists on older ideas, the same goes for your observations and ideas on tech.

An email subscriber is worth 100x twitter or LinkedIn followers or whatever other stuff is out there. An email = a real channel

For a professional audience, at least, email is the only KPI I care about. Nothing has more engagement. And importantly, to a previous point, it’s independent/decentralized and will clearly be around in a decade – it’s hard to say that about any of these other subscriber metrics. Given that, I focus on my blog’s UI on collecting emails – both on the homepage, at the bottom of essays, plus those annoying popups that are (unfortunately) super effective.

I started writing while working at a VC. They asked, “Why give away ideas? That’s your edge.” Ironic that VCs blog/tweet all day now ;)

It took a long time for VCs to figure out how to market themselves and their ideas :)

Publishing ideas, learnings, opinions, for years & years is a great way to give. And you’ll figure out how to capture value later

The first year of writing, I had an audience of hundreds, including friends/colleagues from Seattle, my sister, etc. It wouldn’t be until a year later that I figured out it was a helpful asset when you’re going out and trying to raise money for a startup! And years after that, to help get your company acquired. And a great launching pad for market research and side projects too!

Creating is the thing – writing is a subset
For me, writing on this blog has been a real gamechanger in terms of building relationships, a professional reputation, etc. But it’s just one potential method of creating and putting content out there. Maybe your version of this is through videos, photography, or podcasts. Or maybe you’re a developer and want to keep shipping open source projects. All of it can work. The important part is just to start giving out your knowledge and ideas – and over time, to build that into a platform for other activities.

Just get started and I doubt you’ll regret it. And to those who’ve been reading my work for the last decade, thank you! I appreciate it.

PS. Bonus lessons
To close, I’ll point you to some bonus ideas from an old essay, How to start a professional blog: 10 tips for new bloggers, written when I was just starting:

  • Carpet bomb a key area and stake out mindshare
  • Take time to find your voice
  • Stay consistent on your blog format and topic
  • Just show up
  • Go deep on your topic of expertise
  • Meatspace and the blogosphere are tightly connected
  • Embrace the universal reader acquisition strategies for blogs
  • Come up with new topics with brainstorms, news headlines, and notes-to-self
  • Look at your analytics every day
  • Don’t overdo it

More details here.

PS. Get new updates/analysis on tech and startups

I write a high-quality, weekly newsletter covering what's happening in Silicon Valley, focused on startups, marketing, and mobile.

How to build a billion dollar digital marketplace – examples from Uber, eBay, Craigslist, and more

Marketplaces are easily underestimated
When marketplaces get big, they can get really big. Some of the biggest tech successes ever – eBay, Airbnb, Alibaba, Uber – are marketplaces worth tens of billions of dollars each.

And yet marketplaces often start small, in niches and weird corners of the Internet. As we all know, when eBay got started in 1995, it was focused on collectibles. The venerable venture capital firm, Bessemer Venture Partners, famously passed on an early investment:

“Stamps? Coins? Comic books? You’ve GOT to be kidding,” thought David Cowan, a partner at Bessemer. “No-brainer pass.”

An early investment in eBay would soon yield a 50,000% return from Series A to after the IPO, as the company started to help transact on everything from electronics, cars, homewares, and more.

Two decades after eBay was founded, a similar story unfolded itself, this time over Uber (my current employer!) and the taxi market. NYU Professor Aswath Damodaran asserted that Uber was overvalued after a 2014 investment round. Based on data points from the global taxi and car-service market, he concluded the real number should be $5.9B. Since the 2014 article, Uber has blown past his estimate by 10X, with top line revenues to support it. Not bad. The reason the estimate was so off, as investor Bill Gurley pointed out, is that Uber goes beyond taxi use cases and grows the market substantially by unlocking many new categories of transportation. Another example of going from niche into more use cases over time.

(As an aside, a slightly different flavor of the expansion of audiences and use cases leading to wild underestimates – this time my mistake: Why I doubted Facebook could build a billion dollar business, and what I learned from being horribly wrong)

Starting small, and what to do next
In both the eBay and Uber examples, we see that you can start with a niche – whether that’s a geography or product line – and then quickly scale into a huge network of buyers and sellers. It turns out that there are a couple key moves to make this happen, and today I’ll highlight some of the main strategies with examples across the past few decades:

  1. Expand into new geographic markets
  2. Add new products and price points
  3. Decrease friction from signup to successful transaction
  4. Grow supply + demand stickiness

Let’s dive into each one.

1. Expand into new geographic markets
Marketplaces like Uber, OpenTable, Craigslist, and others are hyperlocal in nature, and a critical mass of supply/demand must be quickly built within a constrained geography. If a customer is trying to book a restaurant in the Hayes Valley neighborhood of San Francisco, you don’t care much how many restaurants are also on the platform in Manhattan.

As you might imagine, breaking into each new local market can be incredibly painful. Marketplace companies often end up employing teams of “launchers,” a specialized ops role focused on cracking new cities.

Here’s a great Quora writeup on Uber’s Launcher team from Chris Ballard (these days, GM SoCal):

The “Launcher” role at Uber is one of the most physically, emotionally, and mentally challenging roles that an individual will come across.  It is also one of the most rewarding. […]

Once in a city, the Launcher must simultaneously:

  • recruit, hire, and train a local team
  • develop partnerships and manage relationships with local hire car operators (NB: Uber does not own any vehicles.  We work with existing accredited, licensed, and insured hire car owners)
  • create a marketing strategy to scale the client base and increase visibility
  • explore biz dev opportunities (sponsorships / partnerships / co-promotions)
  • form relationships with local press
  • throw a legendary launch event to officially kick off the city!

The travel is intensive.  Launchers are on the road over 300 days per year.  We live out of suitcases, and our most important possessions are our MacAirs and our Passports.  If you tend to get homesick after a few days or don’t sleep well unless you’re in your own bed, this is definitely not the position for you.

Launching is hard work, but the good news about these hyperlocal marketplaces is that if it works in one market, then it will probably work in hundreds more. Sometimes there will be stronger cross-network growth across geographies than you initially imagine, enabled by factors like Airbnb’s global travel use case, which can supercharge your addressable market.

Furthermore, if you are a new startup, you can go after hyperlocal markets where your competitors are weak, and build a local network effect that will be hard to dislodge.

2. Add new products and price points
The next variable that marketplaces can play with is expansion of product lines and price points. Both of these directly unlock new use cases and addressable market, and there are strong examples of how this happens. Craigslist, the mother of all free marketplaces, started with events and then expanded to jobs and apartments.

In an Inc interview in 2016, Craig Newmark reminisces on the early form of Craigslist – literally just an email list – and how he intuitively added product categories over time:

Craigslist began with a single email in 1995–you simply shared interesting things going on in San Francisco. What was in that first email? The first ones had to do with two events: Joe’s Digital Diner, where people would show the use of multimedia technology. It was just emerging then. Around a dozen of us would come and have dinner–always spaghetti and meatballs–around a big table. And a party called the Anon Salon, which was very theatrical but also technology focused.

How many people did that first email go to? Ten to 12.

And then? People just kept emailing me asking for their addresses to be added to the cc list, or eventually to the listserv. As tasks started getting onerous, I would usually write some code to automate them. And I just kept listening. At first, the email was just arts and technology events. Then people asked if I could pass on a post about a job or something for sale. I could sense an apartment shortage growing, so I asked people to send apartment notices, too.

Today, Craigslist in over 57,000 cities, generating $700M in revenue per year (on job listings fees!) with just 50 employees. Amazing.

A related move is to offer new price points to the market, which can unlock new use cases and grow the addressable market as well. A good example of this is Airbnb, which provides a much wider set of offerings to guests – from super cheap to super expensive – as compared to their hotel competitors. The low-end of this enables new, higher-frequency use cases to emerge, like weekend getaways. The high-end allows for large family gatherings, like weddings or reunions, to all share a huge house together.

Pricing is a key strategic move because it’s often the main factor for customers, as seen in this Morgan Stanley survey of Airbnb customers:

And of course, we’re also seeing direct product expansion from Airbnb, via their new Experiences product that can be an upsell in addition to accommodations.

3. Decrease friction from signup to successful transaction
The dual levers of geographic and product expansion are powerful, and decreasing the friction of conducting transactions on the marketplace amplifies both. This grows the TAM in two ways: 1) First, directly growing the market because lower friction transactions mean more sales. 2) But also, more subtly, it unlocks more transactions when your marketplace can be incorporated into new use cases that require reliability and ease of use.

For example, few people use taxis to commute, because the service can be expensive/flaky, whereas many folks use Uber POOL to commute because it’s reliable and affordable. You’re bound to use OpenTable more to snag last minute reservations when restaurant inventory is up to date, making it convenient for even casual get-togethers.

There are many ways to decrease friction, but in particular we should look at this from the perspective of the customer (both buyer/seller) through their journey from signup to transaction:

  • Reducing friction from signup to first transaction
    • Signup and onboarding
    • Setting up payment
    • Finding the desired transaction
    • Trust infrastructure (depending on product: Reviews/photos – or ETA – or availability calendar)
  • Reducing friction from the transaction to receiving the product/service:
    • Reliability and consistency – driven by both market liquidity and UX
    • Determining the right price
    • Timing and logistics on completing the transaction
    • Resolving post-transaction issues

Focusing on reducing the friction on the above doesn’t just generate more revenue for the marketplace, but it’s also just a much better customer experience.

4. Grow supply + demand stickiness
Transactions require strong retention of both demand and supply, and if a marketplace can improve that stickiness, more activity can be generated on the platform. In many ways, this is just a classic retention problem, except with multiple players within the ecosystem. Just as you would on a social network product, you can tackle using traditional growth methods:

  • Notifications: Creating a strong notifications platform to engage buyers/sellers at the right time
  • Use cases: Understanding use cases and how to up-sell and cross-sell the stickiest ones
  • Offers/promotions: Using offers and content throughout the calendar cycle to engage
  • Optimization: A/B testing growth levers – from email/SMS/push copy – to when/how to reach out

However, beyond the traditional techniques, we’ve also seen a recent trends towards deeper productization of workflows for buyers and sellers within a platform. This solution, coined in recent years by James Currier and the NFX crew, is to build a “market network” that’s part SaaS tooling and part marketplace.

As a reminder, Market Networks provide useful tools to each side of the market – for instance, OpenTable’s seating system, you get stickiness purely through utility. Combine that with a marketplace, and you get even stronger effect.

Here’s a diagram illustrating the ecosystem:

And below are some examples based on AngelList and Honeybook – showing how multiple players on a market network ecosystem might interact with each other.

As one can see, sometimes these relationships between ecosystem players happen via money, and sometimes it’s through content/community. These rich interactions, facilitated by a great product UX, can retain multiple players and generate a rich stream of transactions. It’s still early years for market networks, and I’m excited to see this sector develop.

Marketplaces can start small, and end up big. Very big. 
To build a billion dollar marketplace, you have to build expansion into your model from day 1.

For some, this will look like focusing on geographic growth and building your team of launchers. For others, it’ll be about adding new product lines and price points quickly, to create new use cases for your market. Or you can improve the core platform, by increasing efficiency – whether that means onboarding or the friction of each transaction. Others can double down on retention, by building utility and workflow automation, to set a foundation for more transactions.

Each of these moves can be valid, and different marketplaces will do each. Or perhaps all of them!

PS. Get new updates/analysis on tech and startups

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VIDEO: Three things you need to know to raise money in Silicon Valley

 

Raising money is hard. And it’s even harder if you’re an entrepreneur from outside the Bay Area.

Entrepreneurs from outside of Silicon Valley often struggle to raise money here. There’s issues with culture and style, differences in expectations, as well as our emphasis on growth over monetization. I’m reminded of this every time I travel and meet startups. Earlier this year in Paris, my girlfriend Brianne (at Zendesk!) and I gave a talk that touched on many of these issues. We recorded the session and wanted to share it with you.

The video has a variety of topics, including:

  • How the startup ecosystems are different in SF and in Sydney (and Paris!) (2:30)
  • An alternative to influencer marketing, for startups (5:09)
  • A different way to think about your competition (7:02)
  • Customer service as a competitive advantage (9:25)
  • Why ecosystem matters, and why the Bay Area is cushier than most people think (12:50)
  • Why you should look for failed experiences if you’re hiring or interviewing (14:56)
  • Insights on Uber’s “give / get” program (18:17)
  • Breaking into VC as a teenager (19:02)
  • Advice for starting your own blog or thought platform (26:27)
  • Biggest fiascos working in growth and the downsides to being “too good” at acquisition (29:20)
  • The 4 -5 stages to building a great growth team, and what profiles to look for (33:13)
  • Does the rise of “growth” mean that “marketing” is dying, and should we expect to see the end of the CMO? (36:18)
  • Why you need “growth” when you work in a company with a million-dollar acquisition budget? (39:39)

Here’s a direct link to the video.

For those who are too busy/lazy to watch the video, I want to deep dive on a particular topic: The challenges of entrepreneurs from outside the Bay Area who are pitching investors here.

1. Your company right now doesn’t matter as much as your company’s trajectory.
I’m going to generalize a bit from startups I’ve met from Australia/Europe. One common anti-pattern is for startups to pitch what they have right now, to their detriment. Bay Area investors seek to understand the trajectory of a company. They want to know what it could be in the coming years, and so it’s not good when a pitch is literal and descriptive to the present state of the company. “This is exactly what I’m doing today, and these are the current numbers.” And so on. While this is concrete and feels real, it’s also not the right approach to create a strong vision and narrative that’s exciting.

If you’re a SaaS company, you don’t talk about this last month’s MRR with X% monthly growth rate. You should also talk about how this is the beginning of a platform/suite of products. And why it’s strategic, and sticky, and will be hard for companies to rip/replace in the future. If you’re a consumer startup, then it’s not about how many installs your app has today. Instead, you want to talk about the network you’re building when hundreds of millions of users are actively engaged in your product. And what this will enable you to do that’s unique in the market.

Where the startup is now is just a supporting bullet point to that story about where things are headed.

2. Investor motivations are different. Large outcomes matter more than high probability of success.
The second observation is that Bay Area VCs often have different motivations than investors elsewhereFor traditional Series A venture capital firms, their biggest limitation is not high quality dealflow. There’s a ton of great startups here. Instead, it’s that a partner can only be on the boards of about ten active startups at a given time. Thus, what they care most about is maximizing those ten startups. They want to make sure that those ten are the ten biggest possible companies they could be investing in, with the best possible outcomes.

They care less about whether or not your startup is profitable because that’s sometimes irrelevant to the size of the future outcome. In fact, profitability can be interpreted as reducing the potential scale of the business when the company isn’t growing fast enough. When you can only invest in ten startups and have a billion dollar fund behind you, then it’s all about opportunity cost. I’ve heard a VC say that they’d rather inject more risk into a business to avert a small/medium size outcome ($100M) to have a smaller percentage chance they can get a multi-billion dollar outcome. This can be a disorienting point of view until you understand the economics of a large professional investment fund.

3. At the startup stage, scale and velocity matter more than depth of monetization.
Finally, the third observation is also related to the emphasis on monetization from investors I’ve met in Sydney, Sweden, and France. There’s exceptions of course, but speaking in generalities, investors will naturally have a different investment strategy when they can’t assume that there’s a ton of follow-on funding behind every check. As a result, there’s a focus on getting to profitability so that the company can be self-sufficient.

This also means that there tends to be more B2B and even enterprise startups than we typically see in the US. This is because there certainly are major advantages to that model — you’re able to book revenue faster and show initial traction. But, the key problem that this approach introduces is that it limits the scale and velocity of growth because it’s just much harder to scale an enterprise business than it is to scale a consumerized SaaS or a purely consumer business.

Wrapping up
There’s a ton more content in the video, but ultimately, a lot of the differences in startup cultures for the Bay Area versus other regions comes from these varying investor and entrepreneur motivations. I’ve seen it directly from my meetings with startups from various communities.

It’s often tempting to think that there’s so much investor money here that they’re giving out checks at SFO – and as soon as you land, you’ll get funded. But it’s not quite that easy. For a new entrepreneur to come to SF and succeed, one has to often rethink the style, content, and even growth strategy of their pitch to adjust to a very different ecosystem and set of perspectives.

PS. Get new updates/analysis on tech and startups

I write a high-quality, weekly newsletter covering what's happening in Silicon Valley, focused on startups, marketing, and mobile.

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