Project Precipice Week 4: a breakfast octopus prequel
27week 1 how’s it going
week 2 say hello to inlo
week 3 strategery and defiance
week 4 a breakfast octopus prequel
week 5 brainstorming with bezos
This week, a departure from progress reports to share a previously untold story, a prequel, if you will, to the breakfast octopus story that I had shared for this article from 8 years ago:
Scene: It’s March, 2006 —16 years ago. I’m 34 years old. About a year and a half after launching Woot. A few weeks prior, I took a phone call. “It’s Mike from Seattle,” my assistant had relayed. Mike said word was getting around about Woot and he was a big fan. A few of his colleagues were enjoying it at his office. He worked at Amazon. They wanted to meet me.
My taxi (remember those) pulled up into the parking lot and I get out to this view. Amazon’s early PacMed HQ on Beacon Hill. I can still feel the intimidation competing with my general feeling of excitement. You can’t help but gaze up at those top center windows and wonder who is looking out at you. No-no, I thought. Look down and walk normal.
Now 2006 was long after the dot-com bust and even well into the Web 2.0 era. Amazon had survived but it wasn’t today’s Amazon. They were not infallible or even yet entirely dominant in ecommerce.
That point on their graph seems absurdly low by today’s valuation, but that $36 share price still represented a $15 Billion company, about the same as meeting with Ford at the time (or much of the time since). So it was actually kind of a relief to walk in (and to the right) to a warm little curio-room of culture that served as a guest lobby. Lots of employee crafted signs and fun-looking dot-com memorabilia. A juxtaposed dot-com museum within an art deco industrial era HQ. Even when I spotted the Time Person of the Year plaque, I wasn’t stressed. That was already a relic of the dot-com boom, 7 years prior.
(plus it’s just not a very intimidating photo!)
So, yes, I was to meet with Jeff Bezos for the first time. There were a few others who said hi and then I was led up to one of the top floors. A large empty conference room. I hooked up my laptop and pulled it up to slide one showing my childhood Apple II computer. Then I went through 15 slides trying to explain how @dave and @luke ran a blog and I was a wholesaler. How Woot came about, the press we’d received and the growth we’d experienced.
During my presentation they had pulled up the website and were reading the story of the day and even in the forums scrolling through all the F1RSST!!!1!! / “I stayed up for this?!?!” comments, alternating from snickers at those posts to a few questions on a couple of my slides. Then it was done. Surreal but simple. Everyone got up, shook hands, thanked me and started leaving.
Except for Jeff. He sat back down and motioned that I join him.
“That was great Matt. I love what you’re doing with Woot,” he started. I offered my comments of appreciation for the invite and some sarcasm I don’t recall specifically managed to solicit a classic Bezos laugh. I was really pleased to just get through this experience smoothly, mostly avoiding eye contact and being cheery. And then, out of the blue he asked me a question that made me pause and really take a look at him in response.
What was the question?
Well. First I’ll tell you my answer. Ok, well after 3 or 4 seconds of silence, it was “Uh… I… Um… Yes, I have actually thought about that.”
The question surprised me then and went on to make me far more curious about Amazon and Jeff than I ever expected to be. I shared it with @dave —most of our team had no idea I took the meeting. Over the next few weeks, I offered up terms on which I’d accept a minority investment from Amazon and they agreed to become the only investor in Woot.
Next week I’ll share what Jeff Bezo’s question was and how it actually relates to an early idea we have for SideDeal.
Feel like making a guess? Fire away. Pretend you’re Jeff Bezos in 2006 asking me a question so unique that I remember it word for word 16 years later.
- 69 comments, 76 replies
- Comment
How would you feel about running Amazon?
@YoDad Nope. But I think I had a nightmare similar to that!
2006, so this predates shirt.woot.
My guess: What if Woot offered multiple items a day?
@narfcake classic! but nope, not insightful enough.
Have you thought about what happens when the deal a day fad ends and all of your customers get bored with that model?
@jaybird lol here we are 16 years later Jeff booyah!
nope that would have been a bit on the nose for him also this was more a sense of discovery meeting vs later.
That pic of Bezos makes me think of Pee Wee
@mehsterious It made me think of Jack Nicholson in The Shining.
Would you feel sad turning your baby over to a hack like me?
@sammydog01 you know, this kind of attempted-respect for founders they acquire did come about during the actual transition. folks mean well who say this but selling a business is more like sending a kid to college. and also, nope.
Have you considered diversifying in a way that allows Woot to push stock on hand daily vs solely utilizing the deal a day model.
@tinamarie1974 I very likely had a slide about Woot-offs in there. (That reminds me that this just predates the time we crashed many nodes of AWS with what amounted to a DDOS attack from Woot-Off viewers pressing F5 and refreshing the page towards the end of each sale. Luckily we were friendly with Amazon dev team by then.)
So I would have said we were happy with Woot-offs back then but I see where you’re headed with my SideDeal tease
(but also, nope not it)
@snapster
/giphy back to the drawing board
Have you considered an nth price auction model with a fixed available quantity? https://cpb-us-w2.wpmucdn.com/voices.uchicago.edu/dist/f/1276/files/2018/09/21-28-full-1qgrrp9.pdf
@lehigh this is probably the opposite of a risky click in many ways but I feel a strange aversion. I’ll come back to it.
Well we know how that story ended…
so I’d imagine some question along the lines of being acquired. Or since he is rich trying to entice you by offering to make you rich.
@Kidsandliz “Ok so I am rich and I hereby offer to make you rich” would have been refreshing but nope!
@snapster Hmm… so he is a greedy little bastard then… But then again we already knew that…
I am loving this engagement, this process, and the peeks into history.
As for the question, I think it might have been “Have you ever thought about what it’s like to do the backstroke in a pool of gold coins like Scrooge McDuck?”
The early idea: to replace the balls in a McDonald’s ball pit with a few truckloads of surplus Mardi Gras doubloons and rent swimming time by the hour to nascent YouTubers, but it was really too early for influencer culture to support that model. You could probably make a killing if you had that in L.A. now, though. Until some influencer house just fills their own pool with actual gold coins and it’s all over TikTok.
@djslack
@narfcake in sufficient quantity, coins are definitely a non-Newtonian fluid.
Either get waivers signed or invest in no diving signs.
“Ever wonder what it’s like to be rocketed into orbit…inside a giant dildo? I’ve got plans, Jimmy. BIG plans!”
@StrawHousePig now I want a twilight zone or black mirror build up to that moment where I shake my head and leave the building. Nope but lol.
“If I told you that you had a beautiful body, would you hold it against me?”
@ACraigL security help!
That was my knee-jerk, comedy response. My real guess is:
“Can you syndicate that experience so that you can capture additional market and audiences that are not wooters today?”
@ACraigL where were you when he needed you. nope, his question was simple – no MBA required.
“Have you thought about what you’ll do if you become a millionaire?” Or maybe “Have you thought about what it would be like to be as successful as me?”
@Kyeh nope. I know money is the first thing that comes to mind when thinking what one of the worlds now-richest men would say but I’ll categorically eliminate it to help here. Maybe he asks his kids this to piss them off
“Have you ever thought about dipping pizza in ranch dressing?”
OK so I guessed wrong up higher. What about this guess then: “You want to come to breakfast with me to talk further and eat octopus?”.
@Kidsandliz nope but it would have been funny to then stall him with excuses forever (the breakfast was a few years later)
“Can you get me a B.O.C.?”
(Ok, I know the answer, but I still wanna play)
@dave ha - you know, I might have been equally stunned by this one
“Do you think you could use SideDeal to dispose of very small lots of things we could slide off to you at a really deep discount?”
@werehatrack ha nope - a bit tactical for his level even back then. I don’t know a start date for the SideDeal mention but I doubt it was by this meeting. The Bezos question to SideDeal connect is a fresh one.
“What else would you do if you didn’t have to worry about the money?” (Or maybe I’m still fixated too much on the
…)
@Kyeh it’s a good question but not unique enough for me to write about, nope.
“You looking for an angel investor to help you expand”?
@Kidsandliz I suppose it was implicit that I’d be interested by being there with my cute little slides. not clever enough of him, nope.
@snapster Well then again in the end he turned out to be the devil investor… corrupting and wrecking your baby.
Where do you see yourself in five years?
@tinamarie1974 ha, nope. I wasn’t applying for a job (though I guess that was later mandated by the acquisition)
“Have you thought about what you will do if your company fails?” (Because the failure rate for small business startups is around 90 percent.)
@rockblossom a fun fact: I merged my first company (Synapse Micro, started in 1994) with Woot in 2005 so I was actually sitting there with technically longer tenure than Bezos by a few months. When we were acquired, I was also the longest tenured Amazon employee (until they bought Whole Foods, I figure)
also nope – too blunt of a negotiation question
Have you thought about a live (or recorded) video about the item of the day, ala HomeShoppingNetwork but with Woot trademark humor?
@harder nope, but I like how progressive that would have been. Believe it or not, Youtube was still an independent company at time of this meeting (Google bought them November 2006)
“do you like gladiator movies?”
(i abused /giphy so many times trying to get the right image)
@zippyus well I guess it crapped out on the image.
/giphy Boy Trapped In Refrigerator Eats Own Foot
Some years prior to the Woot! deal I visited Amazon’s PacMed HQ after they had bought my company. Not my company but my employer. Soon after Amazon had an all hands jamboree in a theater in downtown Seattle and I’d guess it was under a thousand employees (back when Amazon’s warehouse was in Seattle). Heady days shortly before the dot com crash.
@zippyus neat. I heard later that beyond the amazing exterior, there were a lot of crazy things wrong with PacMed. Leaks and maintenance issues I gather. The employees that had worked there sure have a lot of amazon street cred though.
was it any of these classic lines?
It wasn’t about the money. He wanted to know if a sellout product, your version of a grand slam or bowling a 300 game, produces a visceral reaction.
@Frcal nope, but this is an interesting topic. It later shocked us how conditioned they were as retailers to see “sold out” as a complete failure of the Amazon customer promise. A first take in how they would change Woot for the better was an assumption that they’d avoid sellouts. You’d be amazed how much energy we wasted saying that meant the price was too high. Around in circles / different perspectives.
Did you ever consider this meeting may have been a trap like what befell Joe Pesci in Goodfellas?
@medz If that’s the proposed Bezos question, it would have been a funny one (nope). If it’s to me from you, then I’d say I remain far more naive than Mr Pesci. I can’t even find a conspiracy theory to support these days.
You ever just wanna build your own rocket and fly into space?
@medz nope as a guess and nope for my answer!
What is your next business after Woot?
@poids nope, this was just a few months from our Wall Street Journal article — I would have just looked at him strange
“You’re the octopus that I’m having for breakfast … When I look at the menu, you’re the thing I don’t understand, the thing I’ve never had. I must have the breakfast octopus.” was what Bezos reportedly said next.
It has become legend in that he didn’t understand Woot!
And IMHO Amazon still doesn’t. Bezos’ Woot! is a far, far cry from Rutledge’s Woot! The Amazon accountants and bean counters have ruined the spirit of Woot! or didn’t, or couldn’t or wouldn’t understand it now or ever.
There was a playfulness and an irreverence of ad copy and merchandisers who, though in business to make money, did not appear to take themselves all that seriously in the Woot! of yore.
Daddy Warbucks and his legends of cringing minions, on the other hand, take him and themselves all too seriously.
Mort and Monty are but a shadow of their former selves.
A Bag of Crap, is just that. A bag of crap. No fun. No suspense. No anticipation. No complaints on not being “in on the deal,” or when the next one is going to suddenly appear or bragging rights on who’s got the better crap or better bag.
Ho. Hum.
Amazon, you clearly don’t understand this marketplace and your customer.
They (Amazon) have no shame in their daily deals offering popcorn or some such on “gourmet” Woot! as it used to be known for $30+ for a half dozen bags or worse. Even their ad copy seems to me to be less and less interesting and far more pedestrian than it was back in the day.
@Jackinga ah but in the prequel, his question might make you think otherwise.
WTF does “Woot!” mean, and how invested are you in holding onto the name?
@G1 that’s two questions. nope, nope.
Have you considered off-loading leftover, broke, returned or other miscellaneous crap in a random grab-bag of unknown contents for which you charge your customers actual money, with enough occasional “jewels” thrown in here and there to make them fall over themselves to acquire, and then complain incessantly about them afterward, but still keep coming back for more?
@ybmuG you know, I sort of assume this was before our first Random Crap sale but I actually don’t know. Wouldn’t it be great if Bezos was credited with inventing the Bag Of Crap. But nope.
Do you want to sell a daily book?
@DTominator I did think about that being a fun model but nope, he was long past bookseller mode.
Have you thought about what you’ll do if this really catches on? Do you have an exit strategy (or retirement plan)?
@xobzoo I imagine we were 350k visitors a day by then — the NY Times and WSJ boosts came early. Nope.
@snapster Sure, but it could always grow, right? (and you didn’t say he wasn’t asking ironically…)
You ever kissed another man?
@medz boy the SideDeal spin off of that question… but nope!
“Are you happy?”
@punkynpye if nothing else that day, I looked happy. nope.
“What is the airspeed velocity of an unladen swallow?”
@macromeh African or European?
@macromeh he’s more of a star trek buff I’ve read. ha but nope.
That building has lines in common with old European cathedrals with an Art Deco overly. Sort of cool looking unlike many of the buildings built today.
@snapster was his question something like
Have you considered creating a subscription for free shipping?
Or something in regards to the VIP membership
@mbersiam nope, that’s a neat guess since the meeting is maybe a year after Prime launched but we’ve already done that across all sites.
“Would you like to see my soul before I sell it to Satan in exchange for world domination?”
@OnionSoup I guess these days it’s that and not being the best damn fiddle player the world has ever seen. Nope.
Have you thought about what you’d do if you didn’t run Woot!?
@callow nope, was essentially a “just launched” thing so status quo was more me not running woot.
Why did you spend time/money to do Woot?
Why does Woot work when so many do not?
Why did I want to meet you?
Questions that can to mind that are not right but curiosity and the cat thing.
@speediedelivery I probably answered the first one in the deck and gave hints on the second. I love the last one if he were to ask it with a bewildering look. nope on all three entries.
“have you thought about starting another company if you sell to me?”
@carl669 selling to them wasn’t on the table (nor was officially even accepting an investment). I would say that his question was good enough to pull me into that process.
@carl669 @snapster I was thinking investing was your motivation for the presentation. Hmmm.
@carl669 @speediedelivery I don’t know how standard it is but this early meeting was devoid of explicit intent and more of a “we’d love to meet you” expressed general curiosity. I suppose even then (2006) it was a unique dynamic for what appeared to be a start-up to have no VC funding or even organized fundraising history at all. Thinking of it that way, they were probably puzzled by the lack of a defining ask from me.
Have you considered competing more directly with Ebay?
@Winedavid49 eBay was less of a scumbag company back then and Amazon still considered them a competitor but I would have bucked that association even if it was to compete. Nope!
Have you thought about your legacy in terms of how your business is impacting the planet?
@GrandmaLyn my appreciation of Bezos increased due to his question but I side with Gates’ “save the planet we have” pragmatism vs rockets to space. Nope, he didn’t impress me with his environmentalism.
I feel like the community should all pitch in and send you a welcome back speaker dock (I joke but I probably bought at least 10 of the jbl docks as gifts for people way back when). As a mostly lurker/occasional irk poster it’s nice to see you again…looking forward to the fun things on meh you and the team think of. also looking forward to my meh streak getting over 100…been here since 2014 and only made it to 98. And that was last week.
@iamdmann @snapster - I still have (at least I think I do) the speaker dock I won when I figured out how many pieces one had been smashed into (statistics scores a win
). Same one you posted in that other read. I’ll trade you that for a decent irk… Postage is on you because I am a VMP 
@Kidsandliz @snapster decent irk…what’s the best irk/irk item you’ve ever gotten? I think for me it would be either hunter boots (my gf’s size) or one of the odd, but surprisingly great feeling foot massagers. either of those beat any of my BoC items as well. Those were the days…mehrathons and irks.
@iamdmann just saw that @snapster even linked to the docks! I had no idea…thank you for the belated (because i suck at reading message threads) laugh!
Putting the Side Deal concept together with his aversion to selling out (apologies if this has been asked and I missed it) I could imagine him asking if you had considered taking the leftovers from the daily deals and putting them up for sale at a higher price until they’re gone.
@ybmuG nope — this would have been an astute but less memorable a question.
Have you thought about a way for the community to curate sales (deals.woot comes to mind)?
@jaybird ah this may be the best guess yet. it brings in an implied understanding of our community that would have very much impressed me. but nope, not it.
@jaybird @snapster how do you build a store with community engagement rather than the other way around?
Would you be interested in flying on a phallic rocket?
@TheSuss another “security help!” moment without context of rockets actually existing
Now I am reading history. Seems like AWS was preparing to launch and fulfillment services were starting. The Sidedeal link from last weeks post was Amazon.
I have more questions but nothing that feels right. I think I know why I work for a company instead of own
Do you know how many Woot customers buy from Amazon later?
What do you need to move to the next level?
Fun fact - I decided in first grade that I wanted to own a candy store. It evolved to a antique shop/second hand type place a few years down the line. Now business services maybe with online consignments sounds right. I see the need but don’t have the vision to put it together.
@speediedelivery regardless of how well-rounded you are in business knowledge or even organizational vision, the entire start-up endeavor is just about filling your skill gaps with others without going broke. If you start something like you describe that people think is fun at a grass roots level, you might find a lot of help waiting.
re: Woot / Amazon customer overlap. Nope on the question, but this (overlap study) was an actual exercise at acquisition years later (2010). I found it really bizarre even at that time that Amazon would be trying to acquire customers that it didn’t have. They already felt ubiquitous to me.
Have you ever considered where the feeling of getting a good deal falls on Maslow’s hierarchy of needs?
What would keep me from copying your company and stealing your customers?
@thegenius one of the absolute best parts of the Woot business was just how difficult it was to compete with, particularly from a larger corporate positioning. Years later I really enjoyed hearing of the exec team lead product selection meetings as they tried to compete with an Amazon daily offering. The community on their Gold Box forums was just toxic.
But alas, he didn’t put that challenge boldly on the table for me to smile back at.
If your customers come to you daily for one item, couldn’t you profit more by changing items every few hours?
@thegenius That would have been a decent observation. I had a few early woot-off slides in the deck I presented that kind of gave away that mode. Also I would have just been snarky and said “you mean like QVC?”
Why hold any inventory and not just 3rd party with companies to sell their items through your customer base? Like a daily store front for a specific item from a series of companies? Wait, am I giving away a great business plan now? I see the point of this post!
@thegenius While it occasionally works well, many have tried this mode full time. I would insist that the magic happens when you negotiate for ownership and more boldly take on the risk/reward. Even Groupon finally tried stocking deals to cut through their boring selections. Dropship offers trend down on deal value due to lack of collective opportunity cost.
@snapster perhaps I’m missing something, but are you purposefully being misleading? The reason I ask is I am fairly certain my last order from sidedeal, some charging cables, came in an envelope from New Jersey and the return address specifically said eBay. Are you engaging in third party sales? Is it part of a test model that you are undertaking to see how it goes? I would assume, that just because other people have tried and failed doesn’t mean that you would initially throw out an idea if you felt you could get it to work.
Edit, not misleading but more misdirecting
@jaybird the initial post was suggesting an all-dropship no-inventory mode which is precarious. Some dropship works out ok.
Have you ever thought about doing a dutch-style auction site and letting the customers find the best price for you?
@oppodude others had back in the first dot-com wave so memory of this was kind of buried as “tried and failed” territory. There was a site for a while that did well called “OnSale” that moved a lot of product. I can’t recall why it failed but probably blame goes to customer fatigue. But nope, not his question.
@oppodude @snapster
With the on-sale comment, this entire thread is a trip down memory lane. That site took plenty of my $$$ and taught me a lot about auctions.
Why just one item a day instead of multiple categories?
And once you have multiple categories, and sub groups - Don’t add a search bar so that it makes it easier to search your site. That would just be F’ing stupid! Make people struggle to find things, group them in odd spots, make categories so close that they are basically the same(sports and OUTDOORS, tools and GARDEN, ELECTRONICS, COMPUTERS, HOME and kitchen, grocery and HOUSEHOLD) Woot is just irritating! /end rant.
@Outer78 heh, that general dimension of sideways growth is mostly my fault. But yeah at some point sprawl got absurd and the bar felt lower on the daily deal. Accepting woot-plus was a cape-waving olé to the Amazon integration team on my way out. I’m sure the team there is much more savvy now.
@Outer78 So, I continued working at Woot (Amazon) for some time after Matt moved on. If I may add my observation… Search on Woot kept coming up and I probably had a part in it getting punted a few times. I always described it as a “disappointment engine”. Searching such a sparse catalog either gives almost no results, or needs some pretty sophisticated knowledge of similarity. If you knew about a specific thing from another site, then search would work, but then that site should have linked you to the item with a monetized affiliate link anyway.
@mschuette That has never stopped Amazon’s search results. I mean, a HDMI cable is totally the same as a SFF-8087 to SATA breakout cable, right?
@mschuette haha, I was just venting cause the site is irritating to try and find something after you have left the site. Things are also cross posted between different sale groups etc. The structure just stinks and unless you use the back button or open in different tabs, you can easily lose where you were. ex. clicking on a humidifier in home and garden now takes you to serious crap under $50 directory.
It would be nice to type “fan” or “humidifier” or “boot” or “grow” and just get a group of crap that falls into that category via the keyword. I can sift through shit on one page but trying to go into each tab to go to each sale group and then having directories change and losing where I was just kinda blows. It’s happened a couple times where I would visit, see some items in a category in one area and wonder if there are more items similar somewhere else and end up just giving up on all of it lol. Again, just my internet rant, I just dont understand not having a search bar. It can be useless and I would still use it. Allow ** (type that into BBuys search:) and let me pull up everything you have on the site, allow sort by price and just let me browse on 1 page. (maybe allow a couple other filters or maybe 96 items/page)
Either way, not having something at all sucks a bit more than having a crappy version of it. That site has too many maze holes to try and find something you want. You either see it right away or you dont and wont even think of looking at the site if you’re shopping for something specific.
@narfcake We weren’t using AUI (Amazon front-end components) or Amazon’s catalog model or Amazon’s clickstream data ingestion (more geared to recommendations). At first because we couldn’t, and then meetings started happening with Amazon engineers like 5 levels above us and they couldn’t comprehend why we wouldn’t be using the same tools as everyone else.
@mschuette @Outer78 heh - now long gone myself, but I picked up the stubborn no search conch shell and still get the blame. Maybe things don’t want to be found?
What’s next?
Who would play us in the biopic?
Will your vision for your company still drive it after you die?
What is the airspeed velocity of an unladen swallow?
@xenophod Have you tried the breakfast octopus?
@joshwassum Not yet! But I will!!!
What will you do next if I buy Woot?
The Amazon tendrils were beginning to creep into everything back then. My guess would be: “What are your thoughts on streaming customized audio-visual entertainment on demand, and cellular video communications? Could it be done efficiently & make it widely available with a low cost to the customer, but make it still profitable to the provider?”
Do you want to
take out our trash for ussell our leftovers?Have you ever wondered what it’s like to be me?
Have you thought how the writing style and forum culture may drive many potential customers away?
Edit: or to put it differently, have you thought how your writing style draws a narrow group of like minded customers thereby limiting new contacts?
@jaybird now you’re just being mean
But yes actually we did/do understand that. It cuts both ways.
@snapster lol, yes, sorry. I knew it could sound mean, but i couldn’t think of a softer way to say it.
Mean wasn’t the intention.
@jaybird @snapster
It could be that it draws in the right customers, though - the ones willing to buy something a bit odd for a good price, maybe.
“If you were to step out of the door here and… hypothetically… say, get hit by a bus, would Woot still be Woot without you there to lead it?”
“If you didn’t have to worry about making money, is this still what you would be doing with your life?”
“Do you ever feel bad about taking advantage of peoples’ emotions to sell them a whole bunch of crap over and over again?”
Pros and cons of puppet troll mascots: Discuss.