The Founding of The Flipside, Part II
Balter’s Essays of Mostly Acerbic Witticisms
Before you read, if you haven’t read part 1, it may be useful to start there. It’s short, I promise.
And pretty good.
That I only pinky swear.
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The Founding of The Flipside, Part II
"I suppose we fooled around and we fell in love."
You know, like, we got married and then, well, then we cheated. And then, well, we now had a mistress we we're pretty fond of, and, well...it's the oldest story in the book.
This probably the best explanation and, once offered, it was hard to unsee. Jim and I had Mylestone. We were two years in, we were top-tier venture backed, we were growing - but it was challenging and we were maybe tired. And here was Flipside, underway, and it felt bigger and bolder and had all-the-wind-at-our-backs type of stuff going for it.
Jim and I pondered: could we run both? Ya know, like double-time?
But that was illogical and surely a fools errand, much like suggesting to a wife that maybe we should all share a new mistress.
(editor's note: both Jim and I have wives, are happily married, and have zero mistresses. Want to keep this straight, this is how rumors get started, ok? This all just an analogy. There are no, like, secret hand signals or anything.)
(PS: Hi Sarah and Jayne!)
Along the way, in an effort to properly disclose the side-hustle that was starting to develop into a full blown bad habit, I called Mylestone's Board Member, Tony Conrad, Partner at True Ventures. Tony and I had a long history together, as he sat on our board at Smarterer through our exit to Pluralsight - and is a hell of mensch ta boot.
Dave (CEO of Mylestone, with a mistress of crypto):
"Hey Tony, it's Dave, wanted to let you know Jim and I have been tinkering with cryptocurrencies, you know, like Bitcoin and stuff - and we actually have set up some investment clubs. Wanted to be sure you were aware."
Tony (True Ventures Partner, Mylestone Board Member):
"Hey Dave, that's interesting. uh huh. crypto, got it. I don't think much about crypto, and really don't pay much attention here."
Dave (hides mistress in closet):
"Yeah, ok, just so you know we're still focused on Mylestone, but wanted you to be aware."
Tony (totally uninterested):
"Ok cool, yeah, thanks for letting me know.” Pause.
"Right. Anyway, How's Mylestone? oh and how's your wife, Sarah?"
And here's where things get a bit tricky: While I thought I was properly disclosing to Tony our weird-as-hell, burgeoning crypto caper - and maybe opening the door to a discussion on conflicting priorities - Tony, thought I was calling him about maybe, possibly, ‘if-only-he-would-consider’, investing in one of our Crypto Clubs. Which, if not obvious from his response, he had absolutely not a lick of interest in doing.
Apparently, if I were, say, an organizational behavior expert, I might offer that Tony and I had 'talked past each other'. And Tony, well, Tony maybe would have been savvily 'switch tracking' me back to Mylestone. And, well, you might pointedly say we were both victims of 'assumption stacking' or, even, generously, 'confirmation bias'.
These, I suppose, if one needed to put a label on things. But really, what good would that do?
The point, of course, is that this conversation was meant to provide some sort of air cover, and ultimately did nothing to unscrew Jim and I from the knotted paradox of choice we found ourselves in.
And this is where a one Adam D'Augelli - another Partner at True Ventures - showed up on the scene. Being 2017 and all, Adam was deepening his learnings in crypto (True bought its first Bitcoin in 2012) and had overheard one of Mylestone's team members (Joe Quinn, social media guru and wearer of pit vipers) talking about our Crypto Clubs.
At this stage, I didn't really know Adam from...well, from Adam. But let's just say he's been profiled as a hardcore Enneagram 7 and is a textbook reading of sorts: He's insatiably curious and incurably optimistic; he's creative and adaptable, and spontaneous.
And so some conversations started; and Flipside's Crypto Clubs were growing by millions, and our science got better and better, and Adam became more and more excited and interested in what was happening.
The complexity, of course, is here we were backed by True from one Partner and were being somewhat pursued by another True Partner - for an idea that we weren't even really working on, but really, actually, totally were.
Wives be damned.
And as if to add another pony under the pile of sh*t we'd built for ourselves, we met with Adam at True Founder Camp a few months later. Jim and I were already so far down the rabbit hole - so enamored with our mistress - that we had a pitch deck explaining our crypto sandbox.
We spun through it. Adam offered, "I don't know about this death business, but this crypto thing is massive and potentially game-changing. Founder Passion is important. And if you can only work on one thing, shouldn't it be the biggest thing possible and the place where you're most passionate?"
The next day was our quarterly Mylestone Board Meeting with Tony. Jim and I still had no idea exactly what we were going to tell him, but I can tell you this, whatever it was, it wasn’t going to be pretty…
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The Founding of The Flipside, Part III to come…