Tag - chicago ventures

The First Time Founder Discount
Why Amazon Has Consumer Investors Bemused and Confused
Ideas Matter
Dude, no one will ever buy that online. AKA how incumbents get pwned in tech.

The First Time Founder Discount

Venture is a cyclical business. But in spite of dire bubble warnings, recent unicorn implosions, and a February 2016 nosedive in public SaaS valuations, the NASDAQ has now been on fire for nearly the past decade. In layman’s term, we’ve been on a (only slightly variable) linear up and to the right curve since 2009.

That is contradistinction to the dot com boom of the late 90s which effectively lasted less than five years, from mid 1995 through NASDAQ’s peak in March 2000 – and, more importantly – was quickly followed by a deep recession which lasted for much of the early 2000s.

The effect of this extended period of abundance is a duration long enough for thousands of entrepreneurs to have raised venture money, struggled, solved, raised more money and exited materially (or failed, and, learned something).

As early stage investors, these founders (repeat founders, serial founders, successful founders, what have you) have become increasingly attractive to invest in because they frequently come with the ability to hire and scale up quickly as well as avoid many of the timely mistakes early in a company’s life that can eat up valuable seed stage dollars. Consider this the venture equivalent of a flight to safety, in an otherwise chaotic, early stage market.

The consequence of this flight to safety is that the early stage valuations of first institutional rounds for repeat founders have ballooned and round sizes have increased accordingly. I took a look at the past 24 months of investment data at Chicago Ventures to break out post-money valuation* and round size dependent on founder profile (n=30):


The highlights are that successful repeat entrepreneurs are raising rounds out of the gate nearly double the size of first time founders ($5.65M versus $2.85M, respectively). Anecdotally, the delta may actually be fundamentally wider as we’ve invested in repeat entrepreneurs far earlier in the go to market cycle (often, even pre-launch) than with first time founders (who typically have significant traction).

The effect of this is that first time founders need to thread often competitive markets on limited resources, and then, even with “traction,” will be blessed with only half the resources of more accomplished peers. This is why I tell entrepreneurs that in spite of press to the contrary, it remains a brutal fundraising market.

If there’s a silver lining, it’s that across both founder profiles, first institutional rounds represent approximately 25% of the fully diluted post-money valuation. Seed/A investors have clear ownership targets and that doesn’t seem to change much based on founder profile.

* For rounds raised on convertible notes I have used the cap on the notes as valuation. I recognize this is imperfect. If all notes converted at the cap, this would actually significantly underestimate the valuations of these rounds (as those caps are mostly pre-money caps) but I’m assuming some % of notes will either not convert (company fails) or convert at a discount.

Why Amazon Has Consumer Investors Bemused and Confused

Amazon’s recent entries into home servicesfood deliveryprivate label clothes & shoes, as well as a wide range of private label home items represent its most brazen efforts ever to attack the entire retail stack as well as penetrate seemingly defensible network effect businesses.

Over the past couple of years, Chicago Ventures has made a number of investments in service-enabled (concierge) commerce businesses believing that their service layer provides a real defensibility against Amazon’s low (no) margin approach. Writing in TechCrunch this past December in “The Middleman Strikes Back,” I noted then:

“If you sell practically any physical good online, Amazon, the Internet’s most powerful retailer, is a perpetual threat. With their distribution, leverage and logistics expertise, they have the wherewithal to undercut on price, and process and deliver products faster than practically any startup — not to mention, they can operate at a loss if necessary.

So where is Amazon exposed? On a services level.

Amazon’s operating margins — already tight at 1.3 percent — don’t allow for much room to train and mobilize a large human concierge force. Which means that building a human-focused, relationship-driven personalization platform actually provides for a tangible differentiator against Amazon — one of the few ways to effectively compete against the giant (and, perhaps more importantly, one of the few ways to build defensibility in a commerce segment traditionally dependent on “brand” as its only de facto moat).

One further point: Amazon is predominantly a destination for directed search – either on a specific product or specific category basis. But as purchasing increasingly shifts to mobile, it turns out that it continues to be difficult to search, discover and catalogue individual items. Concierges – especially when leveraged via a mobile interaction point – reduce that friction and enable a new purchasing behavior.”

But outside of these concierge commerce businesses – which by the very nature of their human capital costs will inherently be lower margin businesses[1] – are there still opportunities to build consumer businesses in a world increasingly dominated (or potentially undercut) by Amazon?

At an event today in Chicago, Amazon employees from nearby fulfillment centers packed 2,000 care packages to send to soldiers abroad who are not able to come home for the holidays Friday, December 4, 2015. Since 2010, Amazon has shipped more than 12 million packages to APO and FPO addresses. The Amazon care packages for the troops included holiday chocolates and snacks alongside an Amazon Fire tablet. The care packages for soldiers headed off in an Amazon branded trailer—one of thousands that Amazon has started to roll-out to increase capacity in the supply chain. Amazon’s Vice President of North America Operations Mike Roth said, “I couldn’t be more pleased that our very first Amazon trailer headed out on the road carrying such special packages—thousands of boxes filled with beloved holiday items and Amazon Fire devices to support troops abroad this holiday season.  (Photo by Peter Wynn Thompson/AP Images for Amazon)

Although many investors and operators I’ve asked privately have expressed mostly bemusement or skepticism about Amazon’s recent efforts, I’ll admit that Amazon has me perpetually on edge.

On Brand Authenticity

On a recent swing through the West Coast I asked several experienced e-commerce entrepreneurs (generated hundreds of millions in annual revenue, raised hundreds of millions of dollars from bulge bracket VC firms) the Amazon question.

The responses were similar: that it is fundamentally unlikely for Amazon to win a branding war in many product categories. For example, one founder noted, Proctor & Gamble or Johnson & Johnson, both of whom are seeing many of their product categories be unbundled by startups, lack the credibility to build authentic new brands in today’s social and content based environments.

How can a corporation claim to represent certain values as underpinning its products when its entire history of operations has been largely antithetical to those same values? Consumers, he argued, are simply too well informed now to be tricked by that ruse.

That strikes me as true – in certain categories. Here’s my view on how many product categories break down from a consumer’s perspective on importance. For context, I believe that purchasing decisions primarily hinge on four variables: Recall Impact is the speed at which a name brand is immediately recognized by a consumer, Authenticity Impact is the natural fit between company (or founders) and its product and messaging, while Review Impact refers to the import of 3rd party or peer-to-peer product reviews.


The takeaway is that authenticity matters – but not always. Bargain shoppers are focused less on company values and story and a lot more on trusted brands who will provide a consistent quality of product at a low price point. Whereas mid-tier buyers care a lot less about traditional household brand names and base far more of their purchasing on crowd sourced information and reviews. This trend is more eloquently described by Itamar Simonson, a Professor at Stanford GSB who argues that we’ve reached “the decline of consumer irrationality,” that is, a large segment of consumers are less malleable to high level branding than in the past.

Amazon’s platform allows it to potentially excel within reviews, recall and price. Reviews, because it has habituated its customers to checking peer reviews before purchasing (and if its products warrant positive reviews, consumers will take note), and Recall, because the Amazon name is effectively ubiquitous with quality and convenience.

What this means is that Amazon has a very credible case to steal market share from bargain brands and mid-tier brands, but will face resistance as it moves into categories where authenticity matters a lot or if its product is subpar, irrespective of price. This is likely why its AmazonBasics line has fared well (low cost, commodity products, mostly electronics), whereas its initial line of diapers was pulled from the market. I am personally suspect that its forthcoming “Mama Bear” line of baby products and organics will be successful

On Irrationality and Execution

As an investor, my job is to pick and help businesses that I believe can execute on models that are defensible and sustainable. But Amazon has shown an unwillingness to accept any network effect as impenetrable and a preference for building, rather than acquiring.

That said, the questions I wanted to unpack are: (a) Is Amazon likely to out-execute a focused, fast growing startup and (b) Are they rational?

Let’s start with (b) – are they rational? I asked a respected consultant to the Fortune500 on strategy and corporate development with deep experience in retail. His thoughts:

“Amazon has always had a very unusual way to do strategy, breaking many of our rules.  But along the way, they have also proved that it is a very bad idea to do that.  How do I know that?  Look at the profit margin per sales dollar, the profit margin per employee, and simply the lack of net profit over the many years.  They are masters at “trading dollars” rather than making money.  Until very recently, profits have been essentially zero.  Never before in history has a major retailer grown without making buckets of money all along the way.

Along the way, to provide the appearance of dynamic growth, they have aggressively been crashing into markets and selling things at or below their real cost (including all true costs of operations).  How do I know that?  They make no money in the end, and that shows me their true costs, which they work very hard to hide in the individual business sectors.

Amazon does appear to act irrationally, and it is only the superior irrationality of the stock market that allows them to have the capital to do that.  Can the profit from AWS actually support the entire enterprise?  I have no idea.  But I would not want to compete with Amazon in any product space.”

Irrespective of whether one is an Amazon bull or bear (and I think it’s important to learn Chamath Palihapitiya’s take on the bull case) it does appear that their actions in any given business unit are highly experimental, to the point of appearing irrational (though employees will tell you Amazon is extraordinarily data driven). As an operating business, they are either fools or geniuses – both of which are reasonable perspectives – but many of their business launches do appear irrational. For example, Handmade, a direct Etsy competitor announced more than a year ago, has yet to launch and seems an odd market to attack given that Etsy’s market cap at $1.1B, or 33bps of Amazon’s, is downright immaterial.

The second question worth exploring is whether Amazon is likely to out-execute a more nimble startup. Amazon’s past is riddled with failures such as the Fire phone, Amazon Local (its investment in Living Social was also unsuccessful), and others. Whereas its successes, led by Amazon Web Services, Prime, and Echo are undeniably game changing. The reality, like most of life is likely grey – that Amazon’s outliers are outnumbered by its hundreds of somewhat successful experiments

Insights From Public Markets

To date, Amazon’s aggressive low cost pricing and capex-intensive logistic arsenal has most visibly punished traditional brick & mortar retailers. Sears, Macy’s, Nordstrom, Williams-Sonoma, Kohl’s and others have all lagged the S&P 500, often precipitously, for more than five years. In the following two graphs, the S&P 500 is the blue line.



But there’s one glaring exception (in the second graph). Off-price retailers, led by TJ Maxx & Ross Stores have surged, doubling the return of the S&P500 over the same period, and trading at multiples double to triple those of traditional retailers:


In fact, the three brick & mortar retailers with the highest multiples: TJ Maxx, Ross Stores and Michael’s share one unique characteristic: they have effectively zero e-commerce. In fact, the retailer with the next highest multiple is Costco – who do not rank in SEO and whose e-commerce gated and exclusive to annual members.

So what’s the logic? Has Wall Street simply lost its mind & just hates online shoppers?

No. Each of the retailers in the high multiple bucket shares a commonality: a perception of being Amazon-proof. Off-price retailers have a particularly complex business model: frequently changing merchandise, material inventory differences on a store-by-store and geographic basis [3], and opaque relationships with the brands themselves. Those are complexities that are difficult to productize online because of the fast changing nature of the inventory – and for the time being the street assigns a premium to that non-commoditized revenue. [4]

The same is true of both Costco and Michaels. Costco, historically, has enjoyed a structural moat against other retailers because of its membership club and unique approach to high volume/bulk items. That, of course, may be changing – sales were flat for the first time in six years in the last quarter – and it’s possible that slowdown is related to Amazon’s Subscribe & Save. Michael’s stores, the behemoth craft superstore also trades at a material premium to most retailers, presumably because of a combination of (a) its custom framing business, a major revenue driver, has been reluctant to transition online and (b) over 50% of the store’s product revenue comes from private label brands, insulating itself from selling purely commoditized supplies.

High level – these are the insights investors and entrepreneurs should be focusing on when innovating in direct to consumer businesses. With an effectively infinite war-chest and a fearless leader, Amazon’s willingness to compete, even with mid-cap companies such as Etsy and Grubhub is unprecedented and its potential impact, significant. Those insights suggest a focus on building deeply authentic products, innovating in product mixes that are not naturally leveraged by Amazon’s existing logistics, and/or focusing on defensible transactional network effects businesses[5] – while avoiding mid-tier, commoditized product tiers or businesses that compete on logistics.

[1] There may be exceptions. There’s a reason Stitchfix has been investing heavily in data science, reportedly employing 60 FT data scientists. Data, even if only partially automated, is they key to reducing these concierge related overhead costs.[2]

[2] The paradoxical element of it all is that if a concierge commerce business (such as Stitchfix) becomes a purely data/AI personalized retailer, then they have unknowingly just played into some of Amazon’s greatest strengths: data leveraged personalization. It would seem there is a balance to be struck in this cycle.

[3] As an aside, one of the amusing nuances of the off-price retailers is that because of their changing inventory, and store-to-store inventory differences, each visit provides a sense of surprise and often delight – that same “surprise” many of the e-commerce based curators have tried to recreate online with mixed success. Turns out you could’ve just walked into an off-price store all this time!

[4] This is also why I am personally intrigued by the online consignment players. TheRealReal for example has enormous operational complexity because of the one off nature of its inventory – and forced to streamline processing costs (photography, content, authenticity verification, tagging) to the point of being profitable even on $100 items. Our investment in Luxury Garage Sale takes this complexity even further: moving thousands of truly unique SKUs across the country to its different retail stores, and even further re-leveraging the consigned items by putting them in try on at home and return boxes, called Luxbox

[5] Grubhub’s network effects, though strong from a technical perspective, are arguably weaker as consumer behavior shifts towards expecting a holistic delivery experience. This is because the company at present does not fully control that experience. Amazon, by virtue of its logistical prowess, can begin to recast the network in its favor, especially if it is willing to undercut on price and subsidize the costs of speed. Whether that is cost effective for them is irrelevant – Amazon is not concerned with short term profits.


Ideas Matter

The debate amongst venture capitalists over whether to prioritize markets or people in investment decision making is as old as the industry itself.

Fred Wilson, famously authored an oft quoted 2004 blog – Execution Matters, Ideas Don’t – which referenced USV’s failed incubation of FaveMail leading to the following conclusion:

“The lesson i take away from the whole thing is great ideas don’t make great investments – great entrepreneurs do.”

Three years later, Marc Andreessen, co-founder of Andreessen-Horowitz, opined differently in “On product/market fit for startups,” noting:

In a great market — a market with lots of real potential customers — the market pulls product out of the startup.

The market needs to be fulfilled and the market will be fulfilled, by the first viable product that comes along.

The product doesn’t need to be great; it just has to basically work. And, the market doesn’t care how good the team is, as long as the team can produce that viable product.

Most recently, University of Chicago Professor Steven Kaplan in his 2009 study “Should Investors Bet On the Jockey or the Horse” in the Journal of Finance concluded:

The results for both of our samples indicate that firms that go public rarely change or make a huge leap from their initial business idea or line of business. This suggests that it is extremely important that a VC picks a good business. At the same time, firms commonly replace their initial managers with new ones and see their founders depart, yet still are able to go public, suggesting that VCs are regularly able to find management replacements or improvements for good businesses.

In spite of Andreessen’s comments, I would say that the working consensus in the early/seed stage venture world for the duration of my tenure has been to bet on special people and let the rest fall into place. That approach was verbalized in my interview with David Hornik on this blog where he outlined his investment approach as “people, people, markets, people.”

But the world is changing. The vast majority of companies I’m referred to are largely derivative ideas of larger tech/startup competitors. Problematically, this is actually fundamentally different than going after large monolithic incumbent corporates in a given space. For whatever reason I think it’s because entrepreneurs are trying to improve processes/better execute on problems rather than re-imagining the reasons those habits/processes even exist.

My sense is that the market is cycling back to the importance of bold, unique, creative ideas – above and beyond the obvious focus on “big markets” or “founder/market fit.” Of course people still matter, just as a large addressable markets have always mattered, but in my estimation there is a subtle yet undeniable shift of interest away from improved processes/products towards ideas that challenge the fundamental assumptions underlying the existence of those processes or products themselves.

In that vein, I was recently asked to prep some talking points for a firm offsite on the state and challenges of investing in consumer tech. I’ve attached those slides here. The theme was very clearly that we are in the “reimagination” stage of venture and my observation is that companies solving pain points but not re-imagining or re-conceptualizing consumer behavior are out of favor with top tier investors.

[Note: It’s always nerve wracking putting detailed thoughts into the market – I’m sure a lot of people disagree with me – but I do appreciate any feedback and counter-examples of places where I’m wrong.]

Dude, no one will ever buy that online. AKA how incumbents get pwned in tech.

I’m blessed to work at Chicago Ventures with some extraordinary people who are continually pushing me to evaluate whether I’m too accepting of the status quo, challenging me to re-imagine the future, and, ultimately, the types of investments we make.

Most recently my colleague Pat Ryan Jr. pointed me to a recent Fred Wilson blog, Don’t Automate, Obliterate, and the corresponding Harvard Business Review article. Tl;dr? Cliff notes are that it’s far more valuable to re-imagine an industry from the ground up rather than trying to build an efficiency focused, automated piece of software on top of it. Two examples: Instead of building call routing and dispatch software for the taxicab industry, re-imagine the taxi industry as P2P ride sharing, a la Uber. Or, instead of building document management software for the legal industry, fundamentally re-consider what the legal world might look like under a crowd-sourced model, for example UpCounsel.

The whole discussion reminded me of a conversation I had with a well known VC about three years ago in NYC. In it, he reminded me that in the early days of e-commerce, shoes were considered an untouchable category – “who would ever buy shoes online? You need to try to them on!” And they remained elusive until Zappos came along and offered a seemingly implausible value prop: what if we were to ship you unlimited shoes for free? Let you keep them for a year to try them out? And then let you return them for free? We all know how that story turned on.

Similarly, he noted at the time, furniture – sofas, mattresses, tables, etc – were one of those categories that hadn’t been cracked by e-commerce. The unit economics made delivery expensive. And, like shoes, consumers wanted to try them on. Is it comfortable? Do the colors match up with room palette? What if, he proposed at the time, a furniture company offered the following value prop: We’ll show up at your home, for free, with ten different sofas of varying feels and colors, let you try them all out for free, and then just keep the one you want and send all the rest back for free?

Compelling. But entirely impractical, if not outright impossible. Right?

Enter Casper.

If you’re not aware of Casper, they’re a web-only millennial focused mattress company promising free delivery within 90 minutes in NYC, a 100-day try out policy, and free-returns (for any reason) if you’re unhappy. Oh, and they’re a fraction of the cost of traditional Serta, Stearns&Foster, Tempurpedic mattresses. Oh, and they come with a 10-year warranty. Oh, and the reviews are off the charts. Oh, and it goes on and on.

Casper actually was an impossibility. Until very recently. Its success is a combination of the availability of low cost on-demand delivery (powered by Zipments no less! [Disclosure: Chicago Ventures is an investor in Zipments]), reduced costs via vertical integration, and innovative customer acquisition channels. Most importantly, Casper is evolving into a lifestyle brand.

Casper exists because its founders elected to challenge incumbent assumptions about what a mattress felt like, how it could be purchased and what it would cost. While their new assumptions were, even recently, implausible, they are now entirely actual.

It is similar to a refrain that famed angel investor Gil Penchina likes to use: “What has fundamentally changed about the world today that enables your business to succeed when all previous attempts have failed?”

As an investor, I am continually scouring the ecosystem for founders who are challenging incumbent assumptions and looking to reimagine industries. Just like it was once considered impossible to disrupt the floral wire services because of their mass marketing spend, David, Farbod & Gregg at Bloomnation challenged that belief by asserting that florists themselves, if empowered with proper tools, could side-step these incumbent middlemen. And they are winning. And florists love them.

Trying to accomplish the impossible can be dangerous – hell, often delusional. But if you’re challenging incumbents because you’ve noticed a shift in the axioms they depend on for success, I’d love to chat.


Copyright © 2014. Created by Meks. Powered by WordPress.