I listened to Wintering: The Power of Rest and Retreat in Difficult Times on Audible over the past week. It was spectacular.

Danielle Morrill recommended it to me. We had an intense up and down journey together with Mattermark, which was doing great until we made a fundamentally bad decision around the company’s strategic direction. The ride down, especially against the backdrop of what I expect would have been a success if we hadn’t made that strategic decision, was extremely challenging. We both learned from it, and it’s been awesome to see the journey that Danielle has been on since.

While I often run without listening to anything, I’ll occasionally listen to a book on Audible on long runs. I started Wintering last week during a run at Hall Ranch. I did another run at Hall Ranch the next day and listened to some more. I run a long loop from my house around McIntosh Lake in the dark and almost finished it two nights ago. Yesterday, I did a few miles in a classic Boulder spring snowstorm at the end of the day and finished it up.

Danielle recommended that I listen to it rather than read it, which turned out to be a great recommendation. The narrator (Rebecca Lee) was incredible. There was so much emotional impact and resonance that I thought it was the author (Katherine May) for a while until I looked it up.

Our entire species has been wintering since the Covid crisis hit. We are just starting to emerge from a literal winter, although the four inches of snow that fell at my house yesterday one of the last gasps of winter trying to hold on. Of course, whether we want to or not, personal winters often appear out of nowhere, even in the summertime.

There’s a paragraph from an NPR interview that sums up whatever review of the book I could write.

Wintering is refreshingly free of self-pitying navel-gazing and trite exhortations to buck up. In fact, May complains about a culture in which we are “endlessly cheerleading ourselves into positivity while erasing the dirty underside of real life…The subtext of these messages is clear: Misery is not an option.” Although she agrees that “Happiness is the greatest skill we’ll ever learn,” she insists that it’s also important to learn about sadness. What she calls wintering is “the active acceptance of sadness.”

I love the phrase “the active acceptance of sadness.” It’s a thing. It’s part of life. I can be for an hour or years. Passively accepting it or actively denying it makes it worse. Actively accepting it is profound.

The post Book: Wintering appeared first on Feld Thoughts.

Amy and I watched Bridge of Spies over the weekend. We enjoyed it, but particularly loved one interaction between the lawyer (James Donovan) and the accused Russian spy (Rudolf Abel).

Donovan: You don’t seem alarmed?

Abel: Would it help?

At multiple climactic moments, the line “Would it help?’ got rolled out.

It had the same kind of resonance with us to one of our favorite movie lines ever (from Argo).

For the past two days, each of us have done call and response using this line about multiple things.

Brad: Are you worried?

Amy: Would it help?

It’s so powerful.

The post Are You Worried? … Would It Help? appeared first on Feld Thoughts.

My partner Chris Moody recently sent around a note on a concept he refers to as Leader Leverage. I encourage every CEO to read and consider it. His rant follows.

Many of you are probably tired of hearing me rant about some form of what I often refer to as “leader leverage”. If you’ve been lucky enough to avoid these rants, the quick summary is that your biggest lever as a board member is the CEO and your biggest lever as CEO is your direct reports. I learned this lesson the hard way running a very decentralized business with 70 offices in 17 countries at Aquent.

A critical learning about a company’s leadership is whether or not employees trust and respect their senior-most manager. Yet, asking this question directly often doesn’t get a great answer. However, asking it indirectly can be magical.

Using an NPS approach, the example below asks the question, “The company is in a position to really succeed over the next three years.” The different answers are by department.

The average employee believes the Company is in a position to succeed over the next three years. The exception is the employees in one particular department (the red box) who all believe the company is completely fucked. This perfectly illustrates the point that the collateral damage of having a bad leader goes far beyond that leader’s ability to perform their technical job because a bad leader will usually poison a team’s perception of the entire company. 

We’ve known for a long time that we needed a new leader in that department for the Company. However, we’ve always viewed the issue with the current leader to be an issue around technical skills. It turns out the ramifications of not having a leader that people can trust and respect goes far deeper.

At Aquent, we found similar results around crazy specific things like compensation where people would go from feeling grossly under-compensated to feeling like they were compensated fairly simply because we made a change in the leader of their market.  

If you found this useful and want more of Moody on topics like this, I encourage you to go watch his vlog Venture Kills. For example:

The post Calculating Leader Leverage appeared first on Feld Thoughts.

Over the past year, we’ve seen an increase of people from across the business and political spectrum join the fight against climate change and pledge to support a greener, more sustainable future. Investors are seeking both financial returns and environmental impact and looking for opportunities to partner with ventures that are working to tackle our world’s biggest energy and environmental challenges.

Enter Cleantech Open, the world’s largest and oldest cleantech accelerator for cleantech, climate tech, and sustainability startups. Through Cleantech Open, startups can build their entrepreneurship skills and professional networks, access expert mentorship, and connect with potential investors, partners, and customers. Cleantech Open is currently accepting applications for its 2021 cohort, and you can learn more and apply here by April 18.

Beth Zonis, the Director of Cleantech Open Northeast, and my wife Amy Batchelor met through a mutual connection. They are both Wellesley College alumnae (Amy is a Trustee of Wellesley College, and Beth is Vice President of her graduating class.) They hit it off right away and found a lot of common ground, especially in their shared passions for Wellesley, the environment, and innovation. This led to our foundation (the Anchor Point Foundation) partnering with Cleantech Open Northeast, the northeast region of Cleantech Open, managed by NECEC as the on-the-ground affiliate. 

Cleantech Open is like a mini MBA for startups. Its mission is well aligned with ours, as Cleantech Open is focused on combating climate change, growing the green economy, and improving Environmental Justice through innovation and entrepreneurship. We are staunch advocates for the environment, and we believe that innovation is critical to addressing many of the world’s challenges.

Cleantech Open has a particular focus on incorporating diversity, equity, and inclusion (DEI) values into its program. It is working to increase the diversity of startups, mentors, and partners engaged with the program. In 2020, 63% of the startups in the Cleantech Open Northeast cohort were founded by women or BIPOC leaders. This year, the accelerator plans to offer programming to educate startups on incorporating DEI values into their ventures.

Cleantech Open Northeast is also creating new curriculum content for this year’s cohort to enable startups to measure their greenhouse gas emissions and carbon footprint to help them build a measurement mindset from the beginning. This is an effort in collaboration with NYSERDA, the New York State Energy Research and Development Authority.

Over the years, many Cleantech Open alumni have progressed to be accepted into other accelerator programs, including Techstars. A few examples of recent Techstars alumni who have participated in both programs are Virimodo, Sunthetics, and SparkCharge.

Virimodo is reducing greenhouse gas emissions in cities by making it simple for buildings to become carbon neutral. Virimodo was a 2018 Cleantech Open Northeast Winner and a Cleantech Open National Finalist and participated in the 2020 Techstars EnergyTech accelerator in Birmingham, Alabama.

Sunthetics is developing software in tandem with electrochemical equipment for more sustainable and efficient chemical manufacturing. Sunthetics was a top 10 team in the 2020 Cleantech Open Northeast accelerator and a participant in the Techstars Heritage Group Accelerator for hard tech.

SparkCharge is making the world’s first mobile and intelligent on-demand EV charging network with a portable, ultrafast charging unit for electric vehicles. SparkCharge participated in the 2016 Cleantech Open Northeast accelerator and Techstars Boston in 2018 and recently had a chance to pitch on Shark Tank, where the company signed a $1 million agreement with Mark Cuban and Lori Greiner.

Cleantech Open is a nonprofit accelerator that takes no equity in its participating startups. This year, Cleantech Open Northeast will award $50,000 in cash prizes, including $10,000 for a carbon sequestration startup that completes the accelerator, and more than $300,000 in goods and services, including incubator and co-working spaces, consulting services ranging from marketing and communications to accounting to assistance on special projects, software packages for startups, and even financial assistance for startups participating in certain states. 

To learn more, register for a Cleantech Open kickoff event between now and the April 18 application deadline. These are great opportunities to meet the Cleantech Open team, entrepreneurs, and mentors. Startups will have a chance to pitch!

Cleantech Open Kickoff Webinar 11, April 13 @ 7:00 PM, Register here

Cleantech Open Kickoff Webinar 12, April 16 @ 12:00 PM, Register here

The post Cleantech Open Northeast 2021 appeared first on Feld Thoughts.

My partner Chris Moody came up with a great idea he’s calling #BoulderStrongTableMesa. This is in response to the mass murder that happened at the King Soopers in Table Mesa on Monday, March 22nd.

What if the Boulder community doubled down on #BoulderStrong to show support for the small businesses located in the Table Mesa Shopping Center directly impacted by this tragedy? After an extremely challenging year trying to keep their businesses running through a global pandemic, the small shops and restaurants of the Table Mesa Shopping Center are now facing the near impossible task of trying to return to business-as-usual. I visited a few of these shops this week and have heard stories of employees hearing gunshots and being forced to shelter-in-place. The parking lots adjacent to King Soopers are occupied by police vehicles and mourners visiting the site. “Trying to hang in there, was a response I heard from one store owner when I asked how things were going. He looked exhausted.  

Moody’s proposal is simple.

Put on a mask and go shop at the Table Mesa Shopping Center this weekend (April 10-11).While you’re shopping/eating, let the employees know you are thinking of them and that you appreciate the service they offer our community.Consider leaving a bigger-than-normal tip! 

His post has a comprehensive list of all the stores in the shopping center. Help everyone who works there get some energy from the community. And – spread the word.

The post Shopping in Boulder at Table Mesa This Weekend appeared first on Feld Thoughts.

One thing that I wish I had learned earlier in my entrepreneurial career is this:

Tools are bought, transformations are sold.

Here's a clip of a talk I gave at the SaaStr conference that elaborates on this.

 

 

First, let's talk about the difference? What do I mean by tools, and what do I mean by transformations?

Tools

Sometimes, the product you are selling is in a category that is well understood. Customers know the category, they know what other products are in that category, and they may previously have used another tool in the category. They don’t have to learn a ton to understand what the tool does. They don’t have to go through an existential crisis to adopt the tool -- it solves a specific problem, and can be implemented without having to rethink how they do things.

Examples of tools are a to-do list app, or a time tracking system. I’m not saying that these products can’t be sophisticated or differentiated, what I am saying is that customers have a pretty good sense for what the product is going to do for them and why they might need it.

Transformations 

Sometimes, the product you are selling is transformational. Adopting it requires customers to rethink all or parts of their business. Often it requires rethinking their career.  It requires transformational change.

Example: The early “inbound marketing platform” HubSpot was selling in our early years. The premise of our product was:  “The way you’ve been doing marketing is fundamentally broken and doesn’t work as well anymore. You’re going to have to do it very, very differently. Our product can help.”  Convincing professional marketers that all the things they had spent their careers doing (and getting good at) was less relevant now (like buying lists, putting up a booth at a tradeshow, etc.) was not an easy thing to do. We were asking for a transformative change in their thinking. 

Change is hard. Convincing someone else to change is even harder.

 

Tools Are Bought, Transformations Are Sold

If you’re selling a tool, you might be able to put a great website up, explain what your product does, perhaps contrast it to other tools in the market, tell customers the price and provide a way for them to buy it. Easy-breezy.  

If you’re selling a transformation, a website is not going to be enough. If you’re asking someone to make a massive change to how they do things, you’re going to likely have to sell.  First, you’ll have to sell them on the reason why change is necessary. Without making that sale, you’re not going to be able to sell them on your particular product.

So, if you've got a transformational product, you're likely going to need sales people to sell it. Not ones that have aggressive sales tactics and worry about how quickly they can close -- but ones that know that the prospective customer has to be sold on the change first before  you can even start to have a conversation about the product.

Tips On Selling A Transformative Product

If ever there was a time you needed marketing, this is it. You need to tell the story of how the world has changed and what companies need to do to leverage the change (or at a bare minimum, adjust to it). When it comes to recognizing the need for change, you don’t have to go it alone. Chances are, there are other companies that also benefit from the particular change you are advocating (just like there were many companies pushing for “inbound marketing” when HubSpot first got started.  Work with other companies (even if they’re competitors) to spread the word, and increase the size of the pie. As you build a base of “converts” that are aligned with how you see the world, work to pull those people into a community.  Help them connect to each other. Support them in their efforts. Recognize their achievements. When hiring sales people, remember that you need people that can help teach people about the change. Why it’s important. What happens if they don’t make the change. Without first convincing the customer that change is necessary, it is impossible to sell them on your product. If you start with “aggressive” sales people that are only interested in selling the product, you are unlikely to be successful. In the early days/weeks/months, recognize that your customers are likely going to need a lot of hand-holding and help. It will feel uncomfortable, because there’s a voice in your head telling you “this won’t scale”. The voice is right -- it won’t. But you still need to do it right now.  For those early customers, you have to go as far as you need to in order to help them be successful. You can worry about scaling later. If you have so many customers that you can’t afford to give them the same level of help anymore, that’s a high quality problem. Much better problem to solve than “We don’t have anybody that’s really succeeded with our product yet.”

I sort of took a Q1 Vacation last week.

2021 didn’t really feel like it started for me until January 21st. Yeah, I took a company public on January 4th, but then January 6th happened. It was a cold, dark, and anxious stretch where January felt like it had about 51 days in it. Then I was deep in SPACland and lots of deals and financings. I definitely had some “I just need to get to March 26th, and then I get a break” in my head.

We got back to Boulder on a Friday, settled into our house on Saturday, and I sort of kind of tried to disconnect (but failed) on Sunday. Monday, I had a full day of work, and a couple of things had landed on Wednesday, so I decided “fuck it” and just worked Monday, Tuesday, and Wednesday before going dark from Thursday to Sunday.

It is delicious to be back in Boulder. The weather is perfect, the birds are singing, and our meadowlark is back in our meadow, chirping away. We missed Cooper (we don’t take him to Aspen), so it has been a fun adjustment to get used to him again (and for him to get used to us.)

I had a monster week of running – mostly on trails. 65 miles with almost 4,300 ft of elevation. That’s the most I’ve done in a long time, and my body absorbed it pretty well.

When I wasn’t running, napping, or eating, I read. A lot. And there are some themes in what I’ve been reading.

Lighten Up!: A Complete Handbook for Light and Ultralight Backpacking: I knew of ultralight backpacking (and have heard the phrase a bunch recently in marketing stuff), but I didn’t really know the parameters or the style. This was a great intro.

Allen & Mike’s Really Cool Backpackin’ Book: Traveling & camping skills for a wilderness environment: Recommended by the previous book. Some new stuff, some repetition. Some ultralight. Some normal backpacking.

Ultralight Backpackin’ Tips: 153 Amazing & Inexpensive Tips for Extremely Lightweight Camping: Again recommended by the first book. I fell into the Kindle content market trap and clicked on links. Mostly repetitive, but good reinforcement on a few things.

Ask Your Developer: How to Harness the Power of Software Developers and Win in the 21st Century: Jeff Lawson and Twilio are awesome. This book is phenomenal, both as the story of Twilio with the underpinning of Jeff’s management philosophy. If you ever use the Marc Andreessen phrase “software is eating the world,” but you haven’t read this book, go read it to understand what the phrase really means. I’m going to host Jeff for two book events: one with Techstars and one with our portfolio. Yes, every entrepreneur and would-be entrepreneur should read this book.

Guantánamo Diary: Now published as The Mauritanian. Amy and I watched the movie a few weeks ago in Aspen when it came out. It was powerful. The book was even more powerful. I wish Guantanamo never existed – it’s a massive negative on American values. I wish Obama had followed through on closing it down. I hope Biden closes it down. If you disagree with me, read the book.

Lost in Startuplandia: Wayfinding for the Weary Entrepreneur: I recently did a talk for a class Ted Zoller teaches at UNC, and he recommended this book. I had it on my Kindle but had never read it. It was a fun memoir-like story of Keller Fitzsimmons’ entrepreneurial journey. Having read hundreds of these by men, I always learn a lot more now when I read one by a woman. It’s excellent.

Living with a SEAL: 31 Days Training with the Toughest Man on the Planet: Another one that had been lingering on my Kindle since 2017. Another recommendation. Hilarious, awesome, fun, and inspiring. I guessed that Seal was David Goggins pretty early on based on what I knew of Goggins. But I had no idea who Jesse Itzler was (now I do.) So, the next book I read was …

Can’t Hurt Me: Master Your Mind and Defy the Odds: Goggins is an epic specimen of a human. But I didn’t really know his story beyond his ultrarunning. It’s an incredible story at many levels. It’s not as fun as Itzler’s book but still awesome and much more inspiring. And it led me to read Itzler’s other book …

Living with the Monks: What Turning Off My Phone Taught Me about Happiness, Gratitude, and Focus: Still funny (Itzler is hilarious and writes well about his own hilarity), somewhat inspiring, but lots of fun. Not as powerful as Living with a SEAL, but now I know Itzler even better.

The Stone Sky (The Broken Earth Book 3): I listened to N.K. Jemisin’s Broken Earth trilogy on Audible while I’ve been running. This series deserves its own blog post and will get that at some point. I think Jemisin may have moved to the top of my contemporary sci-fi writer list. I realized all I was reading were books by white men, so I found a few non-white women sci-fi writers. Jemisin is a world builder at the level of William Gibson and Neal Stephenson and may even be better than them at this point. It was an incredible series.

Not All Fairy Tales Have Happy Endings: The rise and fall of Sierra On-Line: I still remember playing Mystery House on my Apple ][ and being blown away. I spent hours and hours playing Ultima. I felt naughty when I bought Softporn as a teenager, even though the game wasn’t really porn (or even very salacious.) I didn’t know Roberta and Ken Williams, but as an early Apple ][ aficionado, I bought or pirated everything Sierra On-Line did when I was a teenager. And played them all. Choplifter and Olympic Decathlon got more playtime, but Sierra On-Line had a special place in my heart. I loved this book – Ken Williams doesn’t pull any punches anywhere about Sierra On-Line’s rise and fall. It’s a great entrepreneurial software tale from the 1980s and 1990s.

Too Old to Ultra: When a marathon is just not enough: A quick jolt of inspiration from a bunch of storytelling and some advice from a serious ultrarunner who is older than me.

I wish I’d really taken the beginning of last week off. I feel fresher, but after a very busy Q1, I didn’t get the full vacation I needed. Oh well – such is life. At least it’s springtime.

The post Partial Q1 Vacation – Books and Running appeared first on Feld Thoughts.

The following is a guest post by Joe Uddeme the founder of Name Experts. Joe started the company 12 years ago and specializes in complex domain, purchases and sales. I’m a client of Joe and have used him for a number of domain purchases -- but am otherwise not affiliated. I do not make any money should you use Joe’s company. I just found his expertise useful so I am sharing it with the OnStartups community. -Dharmesh

Finding a domain name for a startup is tricky. Particularly with the scarcity of quality domain names that are available these days.If you spend extra time brainstorming the perfect domain name, you may achieve better brand positioning and credibility to keep you way ahead of your competitors, right off the bat.

Of course, it’s much easier said than done. It's often frustrating and takes a tremendous amount of effort. This article will guide you in the right direction and have you closer to that perfect domain name.

Finding a Great Startup Domain Name

Choose a Specific Name

Tools to use when searching for a domain name

Most Brands Stick With .COM

Buying a Premium Domain is an Option

Ideally, a business name and domain name should match. By doing so, a startup establishes a solid brand clients will remember. If the domain is taken, there are some steps you can follow by using a variation of the domain name or using a service that may help you buy the domain (discussed later).

Here are some things to consider when looking for a domain name for your startup:

Sounds positive and upbeat- Avoid negative connotations and meanings. Fewer syllables are also better. Keep it simple - The easier the word is to spell, the better for consumers. Top of mind names are very important when scaling a business. Choose the right Top-Level-Domain for the brand. What is the intent and growth trajectory of the company? That can help determine the ideal URL for the brand positioning into the future. Do your research - After you come up with a name, look it up. Do a legal name search. Does it already exist? Is it trademarked? Are there similar companies or brands that currently trade under your intended brand name?

General words or phrases work okay at times, but specificity is going to be your partner in success. A general name's pitfall is that no real sense of identity is formed, as it's just way too vague.

Not only that, but you'll be competing with literally all the top contenders in that niche when clients are searching. Do a few searches on Google to see what results appear. Make sure there are no competing brands that will make it difficult for your business name to rank on top of the results.

As a startup, you often can't compete, nor are you likely to have the resources to do so. By having a specific name, you can avoid this a lot more. Sure, there's still going to be competitors, but at least you won't be face to face with billion-dollar companies.

 

To guide you towards a more specific name, try to reflect your identity and what your product can do for people. Specificity still needs to sound comfortable and catchy.

Coming up with the perfect name is by no means easy. But, there are tools you can use to help with the search:

Leandomainsearch - A domain generator created by the same team that currently manages WordPress. It’s incredibly easy to use, and all you need is one “seed” word that defines your niche and your brand. Within seconds, thousands of domain suggestions will appear before you. The best part: all the generated names are available for use. Domize - This tool tells you whether your domain name idea has been taken. If the domain name is taken, the tool will tell you how long until the domain expires. For available domains, the site gives pricing estimates on how much it will cost to own them. Namestall - A domain generator with intensive customization options. Like Leandomainsearch, it's super easy, and all you have to do is enter a "seed" word. Pick whether you want the keyword to be at the end or the beginning, enable or disable hyphens, and choose a “word group”. These word groups are a unique feature that allows even more customization to your generated name. Examples of word groups include “1000 top keywords” and “500 popular 4-letter words”. They even have entirely different generators, ranging from rhyming to keyword domain generators. Wordoid - Ever wonder how companies come up with such catchy but somehow made-up words? Wordoid might be it. You can filter the quality, length, and even language of the generated phrases. Go to the filter, and under "pattern", input what phrase or word you want as the basis of the generated word. After the domains are generated, you can see if each one is available and purchase them directly if you wish to. DomainTyper - A reliant and secure way to easily find out if the domain you come up with is available or not. Just type the domain name, and real-time information on the availability of the name will appear. Both unavailable and available TLDs will appear, along with prices if applicable. Use this after you come up with a domain name to polish it up.

New Top Level Domain extensions (TLDs) have added many new options into the market. About six years ago, the Internet began to be flooded with new TLDs. The traditional extensions of .com, .net, and .org, .co, .info, and .biz were now competing with more than 1500 new extensions.

As more supply hit the market with new extensions like .Tattoo, .law and .club started to increase availability and added more registrations to their registries. Many brands began to see the overall importance and dominance of .com.

The .com TLD has existed for almost four decades and is ingrained in our culture and part of the global business dominance that drives the World's largest brands.

A .COM TLD is harder to find and can be more expensive, but your startup's success may significantly increase from using a .com. Users see .COM as the most reliable TLD, helping to build credibility and upside for your brand. Additionally, .COM is the leading TLD in global commerce, and most effective at appealing to the globally-diverse world of business.

A few additional notes: There are a few important notes about some of the legacy TLD’s.

The .io TLD may be considered for tech startups instead. It has gained traction and is becoming a favorite amongst tech enthusiasts. .ORG is a strong tld for health care and professional and non-profit organizations, .AI has grown in popularity with artificial intelligence.

Ultimately, the .COM is the king of commerce and should always be the top target of any emerging brand.

You come up with the perfect name, but it's already registered, or in use. Now what? Though settling for another TLD like .net or .co might sound like a good idea, it can get confused with the .com version. You may also run into trademark issues.

One important thing to do before investing money in the desired domain: Make sure it isn't trademarked. Trademarks can be tricky, and will sometimes require an attorney’s review before potentially spending considerable amounts of money on your domain name.

To test if your domain idea is already trademarked, you can go to the U.S. Patent and Trademark Office website and search the trademark database. If the domain is not trademarked and seems inactive or bought simply for reselling purposes, you may be able to buy the domain.

Attempting to buy the domain directly from the owner can be tricky. Domain brokers are experts in buying domains and can make the process stress-free and easy. Here are a few other benefits of using a domain broker:

Settle at a fair price - Startup owners are passionate about their businesses, and the domain owner may use this fact to inflate the price of the sale. With a domain broker, you stay completely anonymous, and the domain broker handles all negotiation, paperwork and escrow while coaching you through the entire process.  This guarantees a fair price that you may have difficulty negotiating yourself due to many underlying factors. Broker experience - Many brokers have worked in this field for years. With their  experience comes qualification and also relationships. Did you know that about 60/70 percent of the top, aftermarket domain names are owned by domain-Industry professionals? Reputable domain brokers often have long-standing relationships with the largest aftermarket domain owners in the world. This could help you tap into previously inaccessible domain names that would never appear on your radar. Handles the paperwork - An experienced broker will be able to help with all aspects of the transaction from beginning to end. This includes all the paperwork and coordination of the transaction. From soup-to-nuts. Escrow coordination and Speedy transfers between registrars. Remove Emotional Attachment and add a layer of security and expertise to keep things moving forward.

Premium domain names should be treated as such, and require an expert to help negotiate a fair market value for a domain name. In most instances, you only have one chance to secure the perfect domain name, and should take the necessary steps to secure the perfect domain name.

Coming up with the perfect name for your brand is far from easy, and you really have to dedicate a lot of time to it. But it's the centerpiece of your brand. Spent extra time now, and you'll reap the benefits later.

It has been a long winter. Really long. From my perspective, winter has been about 17 months, going back to November 2019. The Covid crisis started just as spring 2020 was beginning. As a result, winter continued through the spring, summer, and fall. And then, well, winter …

I took a half-week vacation last week. I planned for a Q1 vacation, but I had some stuff on Monday and some more stuff on Wednesday, so I just decided to start my vacation on Thursday. I went off the grid, had Amy drive me to Superior, and spent Thursday and Friday running in the mountains back to my house in Longmont. I did an easy run on Saturday and then drove to Waterton Canyon early Sunday and went for a long run there. Between runs, I read a bunch of books and napped.

Being outside on the trails cleared my head and let me completely reset. It’s beautiful in Colorado right now, and even though there continues to be a lot of trauma everywhere, I’m letting my paranoid optimist take over and embrace that we finally are once again in springtime, which is my favorite time of year.

The post Welcome to Spring appeared first on Feld Thoughts.

Disclaimer: I am not an investment advisor or a lawyer. Don’t invest money (fiat or crypto)  based on anything you read  here.This blog post is for entertainment purposes only. Disclosure: I do not own any shares in BitClout (but would like to).

Me: Sorry we haven’t chatted in a while, I’ve been up late nights playing around on BitClout.

Other Me (the skeptical  one): Yeah, I saw you tweet about that. Something about”verifying your account”. First of all, what the heck is BitClout?

Me: It’s a new social networking site built on the blockchain that allows you to invest in (buy shares) in people on the site. It’s like twitter, but you can buy/sell shares in people.

OM: So it’s a trading platform -- where you’re trading in people?

Me: Yes, sort of. I’ve heard Shaan Puri (who's super-smart and even more bullish on BitClout than I am) describe it as:  “If twitter and Robinhood had a baby”.  That’s mostly accurate. It uses its own cryptocurrency called BitClout as the foundational currency

So, for example, similar to twitter, I have a “profile” on BitClout here: https://bitclout.com/u/dharmesh and it looks like this.

OM: Alright, so talk me through it. First of all, why are you even spending time on this? Why are you excited?

Me: Well, remember way back in 2015, which feels like 150 years ago, I invested in this company called Coinbase?

OM: Yeah, seemed crazy at the time, because they let you buy/sell this made up currency called BitCoin. You couldn’t pay rent with BitCoin, you couldn’t even buy a coffee at Starbucks with it.  

Me: Exactly. But it turns out, BitCoin became a very, very real thing, and Coinbase became a rather successful company. Speculation is that they might go public soon at a valuation over $50 billion.

OM: Yeah, I heard about that, kind of amazing. So, you’re saying this BitClout thing is going to be a blockbuster hit like Coinbase?

Me: No, I’m not saying that. I’m saying that people felt similarly about BitCoin back then. They just weren’t sure exactly what it would do or how it worked. To me, BitClout is less about the buying/selling shares in people, but what has me excited about the potential is that it’s the first real social platform that is powered by the blockchain and cryptocurrency. There are so many possible use cases that come to mind.

What has me excited about BitClout is that it is the first real social platform that is powered by the blockchain and cryptocurrency.

OM: What kind of use cases?

Me: Well, since everyone has a currency (they’re called “Creator Coins”) and information about who has bought them is out in the open (because it’s all on the blockchain), then you can use that data to make specific services, features available. For example, I’m also on LinkedIn but I get a ton of spammy self-promotional messages there. It’s very one-sided. So, I have no choice but to ignore most of those messages. But imagine on BitClout someday, I can set a rule:  “If someone owns $1,000 of this non-profit’s coin, their message will make it through to me. It’s like the reverse of spam -- it’s a VIP inbox of sorts. That’s just one idea that pops into my head.

OM: Ok, fine, so say those use cases will exist some day. What can you do *now*?

Me: Right now, it’s kind of like a Twitter-lite (you can post, you can like, you can follow) -- but then, you can buy.  There’s a button right there on the profile page. So, if someone visited my profile on BitClout (@dharmesh), they could buy my Creator Coin for whatever the current price is (right now,,around $5,000).  

OM: Wait, they’d have to spend $5,000?! Why would they do that?

Me: No, it doesn’t have to be $5,000. It can be any amount (because the system deals with fractional coin purchases).  

OM: Ok, fine. But why would anyone “buy” This email address is being protected from spambots. You need JavaScript enabled to view it.

Me: Well, actually referred to in the biz as $dharmesh, kind of like a stock ticker symbol.  Which is weird, but work with me here.  Now, back  to why? Any number of reasons, but the simplest is that they think the price of $dharmesh is going to go up over time, and that they can make a return on their investment. Or, they just like me and trust me.

OM: How does your price get established?

Me: Just like most markets, based on supply and demand, and predictions of the future.

OM: OK, so someone can just put their credit card information in and buy shares in $dharmesh? By the way it feels weird to refer to you as a ticker symbol, but I guess that makes sense.

Me: Yeah, it is weird. Still getting used to that. And no, you can’t use a credit card yet. Right now, there’s a bunch of friction in the system. First off, you have to transfer BitCoin into the system. Then, you have to convert that BitCoin into BitClout -- which is a whole other thing.  And then, you can use BitClout to buy someone’s Creator Coin.

OM: Sounds complicated.

Me: It kind of is. But my guess is that it’ll get simpler over time. But for many that are familiar with cryptocurrencies, they already have a way to send BitCoin to a particular address, so it’s not that big a deal. Took me less fewer than 5 minutes.  (finally using "fewer" when referring to discrete vs. continuous amounts -- yay grammar!)

OM: So, is this something other people should be trying out?

Me: In most cases, probably not. If you’re already a crypto-believer, then sure...take some small amount of it (< $100) and try out BitClout.  Or, if you like to play with All The Things. Perhaps it's part of your job, or like me, you like to believe it is. Anyhoo, buy coins in people you know who you think will rise in prominence. But remember, it’s pure speculation. But, the fact that it’s speculation is not what should hold people back.

OM: Then what should hold them back?

Me: Well, as it turns out, although there’s a way to move money (BitCoin) into the system, and there’s ways to trade within the system, there’s no way to actually move money out. I’m sure that will come, but right now, your money’s locked in there.

OM: Sounds like Hotel California. Kind of sketchy.

Me: It does sound sketchy -- but it’s not. BitClout is not a scam. There are prominent investors behind the project. We know them. It’s not some ghost operation that’s going to take millions of dollars of people’s BitCoin and just run away with it. Could happen, but that’s highly unlikely. But, it’s still problematic for a lot of people that you can’t take money out. I just don't think they've figured out how to (safely) allow withdrawals yet.

OM: OK, so if someone wanted to give this a run, what do they do?

Me: Well, there’s good news. Until yesterday, BitClout was mostly closed to the public (because they were going through some growing pains and the servers couldn’t keep up). So, you needed a password to get to the site. They’ve since removed that. So, you can just go to bitclout.com and setup your account. Be very careful to save that initial passphrase, because you ever lose it, you lose everything -- it’s not recoverable.

OM: OK, so I create an account.  Then what?

Me: Then, for most people the easiest thing to do is give them your phone number so they can verify you. As part of that, they’ll gift you a tiny amount of coin so you can do some minimal things -- like update your profile.  An alternative is to send BitCoin into your new account so you can then start trading. Eventually, you'll have to transfer some BitCoin to do anything meaningful.

OM: Fine. And, back to that weird tweet you posted, what was that?

Me: Well, to verify that my BitClout profile (https://bitclout.com/u/dharmesh) is actually me (i.e. linked to the @dharmesh twitter account), they make you tweet out a special tweet that includes my “public key” (just a random set of letters and numbers) from my twitter account, so then they know it’s me.

OM: It all makes my head hurt.

Me: Like I said, it’s early.  

OM: You actually didn’t say that.

Me: Right. Well, it’s early. 

OM: I’m going back to lurking on Clubhouse. At least that, I understand.

Me: Peace be with you.

Generation X: Tales for an Accelerated Culture is weekend reading for anyone who wants to understand me and my generation.

I was born in 1965 – right at the beginning of the transition from “Boomers” to “Xers.” I’m glad my parents had me in 1965 instead of 1964, where I’d spend my life arguing (maybe with myself) that I’m not a boomer.

A millennial friend of mine didn’t know anything about Generation X, so I sent her a copy of the book. I suppose I was teasing her too much about being a millennial, which was just me mostly being a typical ironic Gen X slacker.

I reread Generation X a few weeks ago, and it held up. The definitions in the margins made me flash back to phrases we used in my early 20s. Douglas Copeland’s brilliant imagination shines throughout. And, at 55, I’ve become comfortable saying “Kids today …” which is what I’m sure my parents (and the boomers) said about me and my generation.

This week sucked emotionally. The Boulder shooting on Monday took the wind completely out of Amy and me. It’s Friday, and I’m winding down for the weekend. Work was intense, so I didn’t have a lot of time to feel my feelings. We were in the car for a while this morning driving back to Boulder from Aspen, so I let myself settle into how I felt. Now that I’m not shocked anymore, the best word I can come up with is “sad.” Very sad.

Grunge is my music. Pessimism abounds in Gen Xers. I’ve adopted the mantle of “paranoid optimist,” which I first heard from Madeleine Albright. At 55, I prefer to be happy and optimistic, but underneath it all is cynicism.

I’m glad to be back in Boulder.

The post Book: Generation X appeared first on Feld Thoughts.

Thanks to everyone who sent a note to me in the past few days about the shooting in Boulder on Monday.

10 people murdered in a city of 100,000 people, in a place that I love where I’ve lived since 1995, is an extremely difficult thing for me to process.

On Monday, Amy and I were shocked. On Tuesday, we were both shaken and stunned. The emotions really hit us both on Wednesday.

Last night I went for a long run with some of my favorite childhood music (Pink Floyd). I listened to Dark Side of the Moon, The Final Cut, and half of The Wall before getting back home. I sat in the hot tub for 30 minutes and then went to bed. I woke up this morning feeling a little calmer but still unsettled.

Some of you have asked if there’s anything you can do. The Boulder County Crisis Fund is the best choice. The Community Foundation: Boulder County is partnering with others to support the victims, their families, and our community in dealing with and processing the March 22 supermarket shooting in Boulder. Some of the partners include:

9News, the City of Boulder, The Daily Camera, iHeartMedia, The Colorado Healing Fund, Community First Foundation, The Denver Foundation, Longmont Community Foundation, Rose Community Foundation, Boulder Mennonite Church, Community Church of Lyons, Congregation Bonai Shalom, Congregation Har Hashem, First Congregational Church, First UMC of Lafayette, Islamic Center of Boulder and Westview Church.

If you are up for making a financial contribution to help people out in the crisis, please make a donation to the Boulder County Crisis Fund.

The post Processing the Supermarket Shooting in Boulder appeared first on Feld Thoughts.

Today’s book recommendation, for anyone interested in venture capital, is The Business of Venture Capital: The Art of Raising a Fund, Structuring Investments, Portfolio Management, and Exits by Mahendra Ramsinghani.

A decade ago, I got a cold email from Mahendra. He was investing in Detroit and eager to write a book about the art and science of venture capital. At the time, Jason and I were just finishing up the 1st edition of Venture Deals: Be Smarter Than Your Lawyer And Venture Capitalist and I was enthusiastic about helping anyone else working on a book that demystified venture capital investing.

I immediately introduced Mahendra to a bunch of Foundry Group LPs, partners, and entrepreneurs. He made progress quickly, and I fondly remember the first edition with the green cover.

Mahendra and I kept in touch. During a book tour for the 1st Edition of Venture Deals, Jason and I visited the University of Michigan. Mahendra cornered me in a hallway and pitched the idea of doing a book together around how a board of directors works at a startup. A few months later, we started working on it.

Startup Boards: Getting the Most Out of Your Board of Directors was released in 2014. Soon thereafter, Mahendra started to work on the second edition of the Business of Venture Capital. Given our recent collaboration, he asked me to write the foreword for the second edition, which was an easy yes for me. The 2nd edition had a blue sky cover and was also released in 2014. In the foreword, I wrote that “VC is a business where each investment teaches you something new – the book provides only a basic framework but each one has the ability to carve a different path in this universe.”

Mahendra recently came out with the 3rd edition of The Business of Venture Capital: The Art of Raising a Fund, Structuring Investments, Portfolio Management, and Exits. It’s now 500 pages and includes much-needed frameworks for culture, diversity, and values that are timely topics when we look at the challenges we have seen in venture capital around gender, race, diversity, and sexual abuse. This time the foreword is from Scott Kapor of A16Z who in 2019 wrote an excellent book on venture capital titled Secrets of Sand Hill Road: Venture Capital and How to Get It.

 

If you have suggestions for the fourth edition, please reach Mahendra at mr “at’ secureoctane.com.

The post Book: The Business of Venture Capital appeared first on Feld Thoughts.

A mass shooting happened at a King Soopers on Table Mesa in Boulder Monday afternoon.

Amy and I are safe. So are our friends and family. But 10 people in Boulder, including one police officer, are dead.

The King Soopers was the one that Amy and I shopped at from 1996 – 2014 when we lived in Eldorado Canyon. I’ve been there hundreds of times. It was at the six-mile mark of my ten-mile run to town. Many friends live within minutes of it, including my brother and his family, my partner Chris Moody and his family, Amy’s current assistant Rebecca and her family, and Amy’s prior long-time assistant Naomi and her family.

Amy’s nephew Jason had gotten his groceries there fifteen minutes earlier. A friend of a board member worked there and snuck out the back. So did a neighbor of my brothers.

Whenever something tragic happens, the quick rationalization is “Well, at least that won’t happen here.” Boulder has always felt incredibly safe to me. I won’t even read a popular crime/thriller novelist whose books are set in Boulder because I don’t want anything to damage my calm.

My calm is very damaged right now. I was going to head out for a long run at the end of the day but couldn’t leave the house. I just sat with Amy, while she doom scrolled through Twitter and texted with friends and family. I ate something but don’t remember what it was. Upon reflection, that sounds a little like a shock response to me.

Last night, an endless set of IMs and emails rolled in checking on us. That calmed my nerves a little, to be loved, but I kept realizing how fragile and arbitrary things are. The phrase “the victims are in our thoughts and prayers” is nice, but it seems so inadequate. We find ourselves in 2021, still in a pandemic, with extraordinary heath, financial, and emotional stress everywhere, and then this.

Boulder has been a special place for me and Amy since we moved here in 1995. Evil showed up in our town yesterday.

The post A Sad and Scary Day In Boulder appeared first on Feld Thoughts.

David Cohen and I recently interviewed Maëlle Gavet, Techstars new CEO. It’s a great way to get to know a little more about her in under 30 minutes.

I met Maëlle about a week before I talked to her for the first time by reading her book Trampled by Unicorns: Big Tech’s Empathy Problem and How to Fix It. I knew I’d like her before we talked, and after almost two months of working with her, I’m psyched she’s at the helm of Techstars.

The post Give First Podcast with Maëlle Gavet, Techstars New CEO appeared first on Feld Thoughts.

Amy and I have been collecting contemporary art since we started dating in 1990. Every morning at our place in Aspen, over morning coffee, we get to enjoy this amazing piece by Julie Maren.

When I wrote the original post, I got a short email from Phi Pham.

I hope you’ll be mindful of collecting art from Black and POC artists too! 

My response was:

We have some, but not mindfully. For example, we are a huge collector of Emilio Lobato.

It’s a good reminder.

Do you have any recommendations for artists in the Western US who are Black or POC?

A few months later, I got another email from Phil with an amazing list that was compiled by Phil and his sister with help from Hannah Leathers and Solomon “Solo” Muhammad,

Phil, Hannah, and Solo – thanks for the great list.

The post BIPOC Artists in Colorado appeared first on Feld Thoughts.

I no longer subscribe to many daily email newsletters, but I’ve kept a few. My favorite to wake up to is Ryan Holiday’s The Daily Stoic.

Today’s headline was It’s Possible to Tune These Things Out but it linked to an older post titled The True Power Behind Stoic “Indifference”.

At morning coffee a while ago, Amy and I had a long conversation about the phrase “I don’t care.” I struggled to explain what I was trying to say and how it was often misunderstood when I said it. Through her reaction and feedback, she helped me better understand what people heard when I said “I don’t care.”

I tried shifting to the phrase “I’m indifferent” instead of “I don’t care.” I continued to feel that I was being misunderstood when I said this. I’d often provide strengths and weaknesses of each option presented but then end with “I’m indifferent.” I knew that this was confusing to some, but I didn’t know why until I read The True Power Behind Stoic “Indifference”.

Of all the loaded words in Stoic philosophy, “indifferent” is one of the most provocative. Marcus Aurelius, Seneca, and Epictetus each tell us that the Stoic is indifferent to external things, indifferent to wealth, indifferent to pain, indifferent to winning, indifferent to hope and dreams and everything else. You hear it enough times and it starts to sound like these people don’t care about anything. Especially since the modern definition of the word means precisely that. But this is a dangerous misreading.

Recently, I got feedback from several people that I was profoundly unhelpful in a particular situation by saying, “I’m indifferent.” I thought about it on a run, which is unusual for me as I rarely focus on one thing during a run but prefer to let my brain go all over the place. In this particular situation, my brain seemed to lock down on the dissonance around this phrase.

The situation in question had two paths: A and B. I had a modest preference for A, but I was good with either A and B. I had explained this, but when asked which I preferred, I said, “I’m indifferent.”

After my run, I explained this more clearly, reiterating that I had a modest preference for A but was good with either A or B. Instead of “indifference,” I stated that I was “tranquil.” After even more reflection, I think a better concept would have been “equanimity.”

Back to the The True Power Behind Stoic “Indifference”.

The Stoics were not indifferent in that sense at all, it’s that they were good either way. It’s not that they didn’t care, it’s that they were good either way. Does that make sense? The point was to be strong enough that there wasn’t a need to need things to go in a particular direction. Seneca for his part would say that obviously it’s better to be rich than poor, tall than short, but the Stoic was indifferent when fate actually dealt out its hand on the matter. Because the Stoic was strong enough to make good of it—whatever it was.

Boom. After reading this, I got the disconnect people were having, which was reinforced by the contemporary view of equating “I’m indifferent” to “I don’t care,” which is very different from “I’m good either way.”

Think of that today, that it’s not about apathy or even a lack of expectation. It’s simply the quiet strength of not needing a preference, because you’re that strong.

Ryan – thanks again for helping me understand myself a little better.

The post What I Mean When I Say I’m Indifferent appeared first on Feld Thoughts.

An Odd Start To My Angel Investing

I started my first company at around the age of 24. It was called Pyramid Digital Solutions and it was a CRM (Customer Relationship Management) company in the financial services vertical. I bootstrapped it, ran it for about 10 years and then sold it to a large software company in an all cash, no attachments deal. Now, I had something I’d never had before -- liquidity. Or in simpler terms -- money. Which, as it turns out is a highly underrated thing (more on that in another blog post). I didn’t make enough money whereby I’d go off buying planes and yachts and such (not my style anyway), but it was enough that I didn’t really have to work anymore.

I did not plan to do another startup. I had done it for 10+ years and lived the notorious startup life. I’d told my wife I was ready to hang up my entrepreneurial hat and get on with the next chapter of my life. To do that, I took the next logical next step:  I enrolled in graduate school (at MIT) working towards an “M.S. in the Management of Technology”. Yep, it’s as cool as it sounds. Kind of an MBA for geeks. I’d always liked school, but never really got to enjoy it and immerse in it, because --- well, that just wasn’t the life I had. Until now. Now, I could pour myself into graduate school and actually enjoy it -- which I did. My loose plan was to get my Masters degree, then possibly get a PhD, and then maybe teach.

My conviction to not do startups lasted only a few...weeks. Best laid plans and all that. 

During classes (which I loved), I missed the startup life. So I thought of an idea: Why not invest in startups? That way, I still get to stay in touch with the thrill of startups, but I could do it vicariously through other entrepreneurs.

Angel investing is like having a niece or nephew. They’re adorable and fun but then you get to hand them back to their parents and go back to your life -- and get some sleep.

My thesis was: I’d get to brainstorm and strategize with the founders, but then I’d get to hand their baby back to them and go back to my (so called) life.

After some quick research (basically Googling for about 10 minutes), I discovered that you didn’t really have to train or be certified to be an angel investor. There’s no skill that was required. There was one simple requirement: You had to be able to afford the risk and that was simply measured by how much money you had -- or how much money you made. So, I discovered that lo and behold, I was a legit accredited investor. So, all I had to do to become an angel investor was to start writing checks.

But, where do I find these mythical startups to write checks to? And, how do I pick them? And, why would they take money from me? As fate would have it, that first year of grad school, I was enrolled in a class at MIT called “New Enterprises”. It was for learning entrepreneurship. (That was not a required course -- I picked it).  During the first week of that class, we all had to do a short pitch of a startup idea and convince our classmates to join our “startup”.  Then, the students would “self configure” around their favorite 5-6 ideas and form startup teams. I pitched a startup called “HubSpot”, which ended up being one of the ideas chosen. Two other ideas that were chosen were “Visible Measures” and “PawSpot”. Both were actual companies (not academic exercises), and I decided to make an angel investment in both of them -- mostly because I really respected the two guys: Brian Shin and Mark Roberge. 

The Entrepreneur vs. Investor Dilemma

During my two years as a grad student, the idea of HubSpot became more and more real. I would get together with one of my classmates, Brian Halligan, and we would noodle on the idea. I’ll save the story of me and Brian for a different blog post, but suffice it to say, HubSpot ended up doing pretty well.  It is now the #1 CRM platform for scaling companies with over 100,000 customers. It is publicly traded with a market capitalization of over $20 billion.

Anyways, back to the story…

I had promised myself I would at least enjoy grad school before "officially" jumping back into a startup and so I held off on officially launching HubSpot until the day I  had my graduation ceremony (June 9, 2006).  I then wrote a seed round investment check of $500,000 to HubSpot. We were off to the races!

Not so fast...

This presented a dilemma for my fledgling role as an angel investor. I’m a big, big believer in focus. And I knew how all-consuming startups can be. So, I figured I’d have to give up the angel investing thing so I could commit myself completely to HubSpot. Presumably, angel investing takes a lot of time -- and I wanted all available time to go to HubSpot.

This was unfortunate, because I liked angel investing. And I thought it could help with the growth of HubSpot too, because I’d learn a lot. And someday, I hoped HubSpot would have many, many startups as customers. [Fast forward to today, HubSpot has thousands of startups as customers, and a special program, creatively named "HubSpot for Startups"]

Ultimately, I came up with a hack which changed everything.

Instead of solving for maximizing my investment returns, I’d solve for minimizing time spent.

If you know anything about investing, you will quickly (and correctly) come to the conclusion that that’s kind of a crazy thing to do. But, if I had to choose between not doing angel investing at all -- and doing it such that I spent near-zero time, I’d rather choose the latter.

So, I setup a weird and wacky set of rules/constraints for myself, all grounded in one simple principle:  Minimize time.

They went like this:

No due diligence. Due diligence takes time. So, I won’t do it. Candidly, at that early a stage, I wasn't sure there was much diligence "due". In most cases, I wanted to deliver a yes/no decision within 24 hours -- and often the same day. I'm just going to write checks.

No calls, no meetings. I’m not going to meet with founders or have phone calls with them. That takes time. I’m just going to write checks.

No negotiating deal terms. I’m not going to “lead” an investment round, because leading a round usually involves helping set the “terms” of the deal (including valuation). And, that takes time and research (and is also unpleasant). Instead, I’ll just make it a rule to accept whatever the terms are that the founders or other investors have decided were “fair”. I just write checks.

No follow-on investments. When startups go on to do subsequent rounds of funding, you often have to choose which ones you’re going to put more money into. That requires due diligence -- which I don’t do. It has the added problem of the “signaling effect”.  For those startups I didn’t choose to do follow-on investments in, it was a negative signal to the market, because people assumed I knew more about the startup than the average person, and if I’m not investing more, it’s probably not a good startup. To remove both those problems, I decided to not invest in follow-on rounds, at all. Professional investors think I’m an idiot because part of the value of making early investments is to be able to “double down” on your winners. But, I’m not looking to maximize return, I'm looking to minimize time. And also, this freed up more cash for early investments in other startups. So, I could just write more checks.

No board seats or advisory roles. That takes time. No accepting “advisor shares” or other perks.  If I'm going to be a user of the product (which I often am), I'm going to be a paying customer. Accepting things for "free" leads to possible guilt for not spending time -- and I was not going to spend any time. Always side with the founders. If ever there comes a time when the founders are making a tough decision involving the investors (like whether to sell the company or not), always side with the founders. If they want to sell. Great. If they don’t want to sell, great. If they want to sell, but the acquirer is putting most of the money into the founders and team and little money is going back to the investors (which happens a lot) -- fine.

Keep startup investments separate from HubSpot. I knew it would be tempting to get companies I had invested in to consider buying/trying HubSpot. It'd also be tempting to get HubSpot to use the products created by startups I had invested in. But, I also knew that would get messy -- and present potential conflicts. Even well-intentioned conflicts have to be explained. That takes time.

You get the idea. Whenever presented with a choice on how I should do my angel investing, I always try to ask myself: What is the option that involves minimizing the expenditure of time?

Shockingly, My Weird, Wacky Way WORKED!

I’m going to preface this section with an important note: DO NOT TRY THIS AT HOME! I am not recommending that anyone try and do what I did. Because what I did was not right.  It just happened to be right for me.

So, at this point, I’m an investor in 80+ companies (this is as of March, 2021).  Since I’m trying to minimize time, I haven’t tried to actually calculate what my IRR (internal rate of return) or even realized return is. But, all modesty aside, I think it’s stunningly high.

Here is a sample of some of my notable investments.

Okta. I was an early investor because I knew Freddie (one of the founders), since he went to MIT too. Today, Okta’s market cap (it’s a public company) is over $28 billion. That ended up being a 300x+ return on investment. Not 300%, 300 times.

If every other investment I had made in the past decade+ went to zero I would still be a super “successful” angel investor on that one investment alone.  (Related note: I’ve committed to Todd and  Freddy, the founders of Okta that I would be donating 100% of my gains in Okta to charitable causes -- thanks again, guys!)  

Dropbox: I have several “batches” of shares because two of the other startups I had invested in got acquired by Dropbox along the way, and I made a direct cash investment as well.  Dropbox is now public, market cap: $11 billion.

WP Engine. A leading provider of premium WordPress hosting.

Life 360: Went public.

Backupify: Acquired by Datto, which then went public. 

Creative Market: Acquired by Adobe.

A few other companies (still private, and growing) that you may know of: Buffer, Help Scout, Drift, Stack Overflow, Gusto, 15 Five, Crayon, Clearbit, Jebbit, Lola, Outschool, Reforge...

Oh, and I’m an investor in Coinbase which has been in the news lately and is rumored to have a valuation north of $50 billion. (Note: this is not investment advice).

Enough bragging. Point is, I did alright.  :)

You’ve Got Questions, I’ve Got Answers

Q: How do you pick which startups to invest in?

A: I tend to stick to what I know (software) and products that I’d use myself, or someone I know would use. And, I invest in people. If you’re thinking: “But wait, you don’t even talk to founders!”. You’re right. I mostly don’t. But, I have a different set of “inputs” (like late night emails). My #1 filter? Seek a low arrogance:accomplishment ratio. I love founders with humility -- and it has served me well.

Q: Why should founders take money from you if you’re not going to add value?

Not all of them should. But, often, they’ll have other investors that want to be more involved -- and provide guidance and help. They require a board seat. The upside to picking me is that a) my money is just as green. b) I strive to be the lowest-maintenance investor on the planet. I don’t ask for a meeting or a call. Or references. Or business plans (yuck!) or much of anything. I won’t blink an eye if this particular startup ends up not working out. I know that’s how things go, it’s part of the game.

Q: How should I pitch my startup to you?

A: Honestly, you shouldn’t. Of all the deals I’ve done, not a single one was the result of a cold outreach or pitch. Especially over social media like LinkedIn or twitter.  I tend to find startups I’m interested in myself. Often, they’re referrals through friends, accelerators like Y Combinator (congrats W21 batch!) and AngelList.

Q: What if I want to be an angel investor?

There are some exceptional resources out there. Look up Brad Feld and Jason Calacanis, they have really great advice and support resources for angel investing.

MBAs have had a bad rep in the startup world for a while now.

This short, fun video I did captures the sentiment -- and also answers the question: Does hiring an MBA into your startup reduce its chances of success?

 

The video shares a story from the early days of HubSpot. 

Here's my advice: Don't shy away from hiring the right kind of  MBAs in your startup. 

What are the right kind? You want the good side of MBAs: The fact that they're analytical, have learned some critical thinking, have likely dug into business cases, can think more strategically, etc. And, you want that in combination with a proclivity to get things done and execute.

The MBAs you don't want are those that would rather spend most of their time writing business plans or forecast spreadsheets (and other works of fiction). Instead you want those that will have animated, well-reasoned debates around hard decisions with tricky trade-offs. You want those that don't just understand the "market" at a macro level -- but understand customers at a micro level.  You want those that will bring a smart, diverse perspective to the table, because they've been exposed to different things -- and have had different experiences than you have.

There's more to creating a successful startup than just building the product. And often, MBAs are a great choice for helping with the rest and putting an operating system in place that will power your startup. 

p.s. I just started my YouTube channel (less than 24 hours ago). I had 2 followers (one of whom is my wife). Will be interesting to see where it winds up in the next 48 hours.

Two of my favorite men on planet Earth have birthdays today.

Happy birthday Dad.

Happy birthday Dave.

I’ve learned an incredible amount from each of you. And, given all the time the three of us have spent together, from both of you.

One of the best things I’ve learned from each of you is a love of wide-open physical spaces. Dad – I’m so glad you and Mom created Woodcreek Ranch.

Dave – thank you for all the 14ers. I hope to climb many more with you.

Even though we’ve spent a lot of time together as a threesome, one, in particular, stands out. We had a Feld Technologies board retreat in the fall of 1987. I remember the date because it was during the Bork confirmation hearing. We spent the time in New Hampshire, drove around looking at leaves, and talking about what Feld Technologies could become now that the summer of 1987, which was full of missteps, was over. We did a huge reset that weekend on what we were doing, which set Feld Technologies on a path where it was profitable every month for the rest of its life. The other path could have been the death of the company, so it remains a potent and formative moment for me.

Happy birthday to you both!

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