Category: Entrepreneurship

Oct 10 2019

JOMO – The Joy of Missing Out

Recently, I discovered a neat new acronym, JOMO, which stands for the “Joy Of Missing Out.”

While FOMO is an endless part of all things technology, entrepreneurship, and investing, I’ve actively tried to ignore and avoid FOMO across all dimensions of my life. On balance, I’m more successful than not on this dimension, but it’s an endless challenge.

I find it entertaining to turn FOMO upside down, backward, and inside out and actively experience JOMO instead.

When I’m depressed, I describe the feeling as “the complete absence of joy.” In general, I self-identify as a “joyful” person. I smile, a laugh, I’m entertained, I’m playful, and I’m generally happy. Even whenever I’m under incredible stress, I still feel, at my core, joyful.

When I think about missing out on things, my joy meter goes to 10. One of my favorite things in the world is reading on a couch in the same room as Amy. For hours. And hours. Or running, alone in the mountains, for hours. Or sitting in front of my computer and writing. For hours. And on Saturday and Sunday afternoons, if I can get in a 90-minute nap, that’s extra joyful.

When I’m doing these things, I’m missing out on a lot of other stuff. And that’s just fine with me since I’m getting enormous joy from the things I’m doing.

I realize that by this description I’ve made JOMO apply to me. I imagine others can apply JOMO in many different ways, depending on what they do that brings them joy. Ponder this for a while.

Not surprisingly, there’s a book on JOMO titled The Joy of Missing Out: Finding Balance in a Wired World. As is my way, I’ve bought a copy, if only to support the author, but I expect I’ll read it soonish.

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Oct 4 2019

Thought Leadership vs. Cult of Personality

In 2011, my now-partner Chris Moody (and then-CEO of Gnip, which I was on the board of) kicked my butt about my endless statements about hating marketing. His thoughts on recasting “marketing” as “thought leadership” appeared on this blog in a post I Don’t Hate Marketing.

It remains a great example of one of the reasons I blog, which is to think out loud, get feedback, learn, and iterate. From that point forward, I changed my entire perspective on “marketing” and now focus almost all of my ideas around “marketing” on thought leadership.

Recently, we’ve seen leaders of several high profile startups implode, along with the current and possibly future expectations around their business. The one everyone was talking about last week is WeWork. Mike Isaac’s book, Super Pumped: The Battle for Uber, which I read a few weeks ago when it came out, is another contribution to this mix. And, there are a number of others, including many who are trying to keep out of the limelight all of a sudden.

A few days ago, I was pondering the idea of a “cult of personality” around a company or an institution and trying to come up with a way to describe when a cult of personality was dominating what was going on within and around a business. In many cases, a cult of personality can propel a company to extremely high profile or valuations, but it can also very quickly cause things to go completely off the rails.

If you ready my writing, you know that I like to use the word “obsessed” instead of “passionate”, and I much prefer working with people who are obsessed with what they are doing, rather than just passionate about it. I think passion is easy to fake, especially around entrepreneurship, and biases strongly toward extroverts. Obsession is almost impossible to fake, and while it can be unhealthy in the extreme, it is a powerful filter for me when talking to entrepreneurs.

While I was meditating yesterday, my mind was particularly noisy. I don’t know why, nor do I judge myself around it, but as I was watching (and labeling) the thoughts bouncing around, simulating a pinball machine in my mind, one popped out and lingered.

Entrepreneurs who create a cult of personality are obsessed about me, me, me.

I remembered the thought again this morning which prompted this post. I now have a simple way to separate between cult of personality and thought leadership.

  • CP: Obsessed about me, me, me
  • TL: Obsessed about the product, mission, idea

When the entrepreneur or CEO becomes the center of the narrative – or more specifically makes themself the center of the narrative – that’s a big red flag from my perspective.

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Aug 15 2019

Venture Deals Online Course – Fall 2019

Techstars and Kauffman Fellows are once again running the Venture Deals online course that Jason Mendelson and I put together several years ago.

If you’re an entrepreneur who wants to raise capital and grow your business, this online course teaches you the basics you need to know for working with VCs. And, if you are starting off as a VC or a lawyer for venture capital deals and you want a refresher on the core issues in a term sheet, this online course is for you.

Venture Deals is a seven-week, collaborative, “learn-by-doing” online course where you will watch videos from us along with doing project work as virtual teams. The workload for the course is about four to six hours per week, includes several live video AMAs with me and Jason, and covers the following topics.

  • Week 1 – Introduction of key players/Form or join a team
  • Week 2 – Fundraising/Finding the Right VC
  • Week 3 – Capitalization Tables/Convertible Debt
  • Week 4 – Term Sheets: Economics & Control
  • Week 5 – Term Sheets Part Two
  • Week 6 – Negotiations
  • Week 7 – Letter of Intent/Getting Acquired

The course is a great accompaniment to our book, Venture Deals: Be Smarter Than Your Lawyer and Venture Capitalist, which is about to come out in a new and improved 4th Edition that will be available by the time the course starts on September 8, 2019.

It’s free, and you’ll be joining over 23,000 people have taken the course in the past. Sign up for the course here!

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Jul 9 2019

Why Gross Profit Is More Important Than Revenue

I’ve been thinking a lot about gross profit (and gross margin) lately. Yeah, I know I can be riveting, but stay with me.

When I was in Boston a while ago (it was very cold, so it must have been January), I had a wide-ranging conversation with Eric Paley. This was before the IPO Summer of 2019 when all conventional valuation metrics have entered the land of “suspension of disbelief” which is short-term good and long-term well-we-will-see-…-eventually

One of our conversational threads was about how to value companies. We ended up talking about using Gross Profit, instead of Revenue, to do valuation analysis.

We’ve been doing this for a long time at Foundry Group. Since we invest across a number of different themes, we’ve had to deal with very different revenue and gross margin profiles since the beginning, whether we realized it or not.

For the purpose of clarity, in my world GP (gross profit) is a dollar amount while GM (gross margin) is a percentage.

Revenue is often equated with Net Sales, which is true in many cases, but Net Sales is actually more precise a measure than Revenue in situations where you have Gross Sales or Gross Merchandise Value as the “top level” revenue number. Also, I often see GM listed as GM%, which is fine. Some people also refer to GM as Gross Profit Margin.

This is regularly confused, even in accounting texts, so depending on which business class you took, you are going to call it a different thing. Oh, and if you use Quickbooks, you’ll probably refer to Revenue as Income, unless you have the current version of Quickbooks where this has finally been fixed. Isn’t accounting fun?

Even if a lot of people realize that SaaS companies have a different gross margin profile than hardware companies, many don’t acknowledge it when playing the valuation game. And, this logic – or lack thereof – applies to marketplaces where GMV is different than Net Revenue which is different from Gross Profit, or Adtech companies which have yet a different “Top Number to Gross Profit” calculation. And, it gets really exciting when a company has multiple revenue streams that include services and derivative transaction-based revenue (say, BPS in a fintech company.)

Today, I’m seeing almost all entrepreneurs and investors in growth companies talk primarily about revenue and growth rate. They tend to adjust the multiples to try to align with a group of comparison companies, but these comps rarely have a similar supply/demand economic associated with the equity of the company in question. And, when the comps are mature cash flow positive public companies, the multiple math diverges even more from anything particularly rational.

I’ve started encouraging the companies I’m involved in to focus on Gross Profit and the growth rate associated with their Gross Profit, rather than Revenue. Try the exercise and see how you compare to the companies you think you should compare to. And think about how much more value you could be creating with the same Revenue number but a higher Gross Margin percentage …

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Jun 7 2019

Deeply Vulnerable Writing on Startup Failure

Jasper Nathaniel recently wrote a long, detailed post titled When Your Startup Fails. It may be the most vulnerable and honest post I’ve read on failure, certainly in a while.

I spent the day yesterday in Grand Junction at Techstars Startup Week West Slope. After a full day of meetings, events, and talks, I ended up at dinner with a half-dozen CEOs of startups in the area (Grand Junction, Carbondale, Eagle, and Telluride.) I was pretty wiped out from the day and general bail out of dinners between 7:30pm and 8:00pm but we ended up going extremely deep on a bunch of personal and emotional stuff so when I got back to my hotel around 10:00pm I was pleasantly surprised with the tenor of the evening.

While there is endless writing about what to do to build your business, how awesome things are going, and why startups are so magnificent, I experience over and over and over again the intense personal struggle for founders and leaders around creating a business where nothing previously existed.

I wish more entrepreneurs would write extensively about their failure experiences in detail.

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May 23 2019

Bad Entrepreneurial Cliches: Strong Opinions Loosely Held

Michael Natkin at Glowforge recently wrote a great post titled Strong Opinions Loosely Held Might be the Worst Idea in Tech.

I have never liked this entrepreneurial cliche. While I have a large personality, I don’t have a temper and I’m not argumentative. I try hard to listen (although I’m not always great at it), try to express my thoughts as “data” rather than “opinions”, and try to evolve my thinking based on the inputs that I get.

I’ve always felt that people who had “strong opinions loosely held” (SOLH) were simply being bombastic. Sometimes I could see that they were being provocative. Occasionally I’d give them credit for changing their mind about something based on new data. But usually, I discount their first opinion (or assertion) since I knew they didn’t have much conviction around it.

Michael’s post opened up an entirely new way for me to think about this, and to continue to dislike SOLH. He has two magic paragraphs in the post. The first is the setup:

The idea of strong opinions, loosely held is that you can make bombastic statements, and everyone should implicitly assume that you’ll happily change your mind in a heartbeat if new data suggests you are wrong. It is supposed to lead to a collegial, competitive environment in which ideas get a vigorous defense, the best of them survive, and no-one gets their feelings hurt in the process.

There’s that word bombastic again. Hang on it to it while we get to the punchline of Michael’s post.

What really happens? The loudest, most bombastic engineer states their case with certainty, and that shuts down discussion. Other people either assume the loudmouth knows best, or don’t want to stick out their neck and risk criticism and shame. This is especially true if the loudmouth is senior, or there is any other power differential.

Unless the other people in the room are also bombastic, the discussion shuts down and the strong opinion loosely held is accepted, or at least reinforced. Power dynamics amplify this – if the leader is bombastic, head nodding ensues. If you are an underrepresented minority in the room, challenging the SOLH can be even more difficult.

Even if, as a leader, you have tried to establish a culture of challenging everyone’s’ opinions, the loudest, most forceful, and most assertive person in the room will often have the leading opinion. It’s exhausting, at least for some of us, to have to fight against that.

I’m not even sure that a “strong opinion loosely held” qualifies as something useful. I’m fine with “strong opinions supported by data and experience.” I’m less good with “strong opinions supported by belief” as I don’t really know what underlies “belief” for many people. But it’s the loosely held part that I struggle with.

Basically, a SOLH is simply a hypothesis. If someone says to me, “I have a hypothesis”, I assume they are asking me my view about their hypothesis. So – when someone presents me with a SOLH, you’ll often hear me ask “do you think that is the truth or is that a hypothesis?” I’ve found this pretty effective for breaking through the LH part.

Michael’s article has a gem in at the end about how to interact with the SOHL person that he goes through in the final section called This (Actually) Won’t Hurt A Bit. I won’t spoil it for you – go read it.

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May 1 2019

LinkedIn Learning: Raising Venture Capital and Validating Your Startup Idea

I recently recorded two free courses with LinkedIn Learning. They are each under an hour long and broken up into a bunch of small segments.

The first one is on Raising Venture Capital and is based on content from the book Venture Deals: Be Smarter Than Your Lawyer and Venture Capitalist that I wrote with Jason Mendelson. Amy tells me that this is her favorite shirt from my current rotation of Robert Graham shirts.

Raising venture capital from Brad Feld on Raising Capital by Brad Feld

The second one is on Validating Your Startup Idea which based on the book Startup Opportunities: Know When to Quit Your Day Job which I wrote with Sean Wise. Same recording studio (an Airbnb in Rancho Santa Fe) but a different shirt.

Evaluating your startup idea from Brad Feld on Validating Your Startup Idea by Brad Feld

The team I worked with at LinkedIn Learning was dynamite. They reached out to me about this and I was happy to give them a day of my time to see how it worked. My goal was that in the worst case I’d give them some useful content to do something with.

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Mar 22 2019

Gluecon 2019 Diversity Scholarships

Amy and I are underwriting the Gluecon 2019 Diversity Scholarships through our Anchor Point Foundation.

Kim and Eric Norlin, who run Gluecon, have had a simple goal around diversity at the Gluecon for many years.

The goal is quite simple: to create as diverse and welcoming a conference environment as we can.

The diversity scholarships are one approach to this. The Gluecon code of conduct is another. Kim and Eric have always been deliberate about inviting a diverse set of speakers and panelists and Gluecon has always been a favorite conference of mine when I’ve been around for it.

If you are interested in applying for a diversity scholarship, send an email to enorlin AT mac.com with the following:

  • a quick biography
  • a short paragraph explaining why you’d like to attend, and how you feel you’ll contribute to gluecon

And, if you are interested in Gluecon separate from this, reach out to Eric or sign up online. It’s May 22nd and May 23rd in Boulder. The topics include things like APIs, DevOps, Serverless, Edge Computing, Containers, Microservices, Blockchain-driven applications, and the newest tools and platforms driving technology.

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Jan 15 2019

Implicit Gender Bias in Startup Funding

While there have been many words written about gender bias in the context of entrepreneurship and funding, I thought the following TED Talk from Dana Kanze presented one of the best frames of references, supported by a real research study, that I’ve seen to date. In addition, she has some clear, actionable suggestions at the end of the talk to help eliminate the bias.

Her research emerges from her own exploration of a social psychological theory originated by Professor Tory Higgins called “regulatory focus.” This theory explores the different motivational orientations of promotion and prevention.

While listening to Dana’s explanation and examples in the video, I had a deep insight – around how to ask questions of an entrepreneur – that hadn’t occurred to me before. Here are her direct definitions of promotion focus and prevention focus.

“A promotion focus is concerned with gains and emphasizes hopes, accomplishments and advancement needs, while a prevention focus is concerned with losses and emphasizes safety, responsibility and security needs. Since the best-case scenario for a prevention focus is to simply maintain the status quo, this has us treading water just to stay afloat, while a promotion focus instead has us swimming in the right direction. It’s just a matter of how far we can advance.”

Dana’s punchline is that investors approach female entrepreneurs with a prevention focus and male entrepreneurs with a promotion focus. Interestingly, she finds this is consistent regardless of the gender of the investor!

The talk has a clear recommendation for female entrepreneurs in it. Basically, if you get a prevention question, reframe the answer in a promotion context.

“So what this means is that if you’re asked a question about defending your start-up’s market share, you’d be better served to frame your response around the size and growth potential of the overall pie as opposed to how you merely plan to protect your sliver of that pie.”

Dana also has a suggestion for how investors (both female and male) can help eliminate this implicit bias.

“So to my investors out there, I would offer that you have an opportunity here to approach Q&A sessions more even-handedly, not just so that you could do the right thing, but so that you can improve the quality of your decision making. By flashing the same light on every start-up’s potential for gains and losses, you enable all deserving start-ups to shine and you maximize returns in the process.”

Her talk is only 15 minutes long and well worth it. Or, if you are a fast reader, take a look at the transcript.

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Dec 10 2018

Category Collapse

It’s the second week of December, which is about the time that all of the predictions for 2019 start occurring. Last week’s announcements of the confidential S-1 filing of Lyft, Uber, and Slack helped prime the pump for some of these. By the way, did anyone other than me think it was a strange turn of events that companies are now announcing their confidential S-1 filing?

Fred Wilson’s post Thinking Ahead To 2019 is worth reading. Unlike the endless stream of predictions that are about to come out, it’s an analysis of the spread between the public market and private company valuations. Fred is not predicting anything in particular but makes several useful observations, including the following:

“And yet storm clouds are on the horizon for the capital markets in 2019. Rates have risen significantly in the last eighteen months, pulling capital out of the equity markets and into the fixed income markets. There are some leading indicators that suggest a business slowdown is on the horizon, which would be the first one in the US in a decade. And, of course, the situation in DC is getting dicey and that will weigh on markets as well.”

Last week I was talking to a friend who is a growth investor. He and his firm see most of the bay area growth deals (e.g. the unicorns stampede to their front door). He made an observation that a number of deals he’s now seeing are for flat rounds with companies that need to raise more money to keep going and he’s feeling the slow down of investor interest at this level. This dynamic is reflected in the article Scooter Firm Chases Funding to Staunch Losses about the current Lime and Bird financings.

Any student of history knows that there is a linkage between the push to the public markets, demand dynamics of the public markets, and the availability and attractiveness of capital in the private markets. If you lived through the Internet-bubble between 1999 and 2002 you know this cycle well. And, you know that the companies that survived it were the ones with very strong fundamental businesses (e.g. Google), regardless of whether they were private or public at the time.

At the same time, entire categories collapsed. The web hosting business – lead by Exodus – almost entirely went bankrupt or was restructured. Out of this mess came several long-term companies and a huge number of pennies on the dollar type acquisitions. If you were on the winning side of this, it was incredibly lucrative, because even in a massive collapse there is a huge long-term opportunity. But you had to be thinking about the economics and capital structure of the business, versus just chasing growth with more equity dollars.

I have no interest in predicting anything, including how any specific category or company will perform. I also have no idea what the timing of anything is. I do know that if you are an entrepreneur or investor, you should pay attention to the context but be very focused on building a durable long-term business. And this moment in time is one that feels like you should be aware of how much capital you have, how you are spending it, and when (or if) you will need to raise more.

Remember – it can all go to zero (a post I wrote when Bitcoin was at $12,000.)

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