Dave Balter · Mostly True Stories

The Founding of The Flipside, IV

By Dave Balter · April 15, 2025 · Work & Money

The Founding of The Flipside, IV

The Founding of The Flipside, Part IV

Tony is slumped in his chair; he's awake, but certainly not fully coherent, and is slightly slurring in response to some of our Board slides.

And this is probably a good lesson in why Benadryl is an ineffective Board Meeting lubricant.

It's October 2017, at True Founder Camp in Carmel, CA, and exactly as you'd expect: Sunny, beautiful, blue sky, birds chirping, trees practically humming. A perfect day for the Mylestone Board Meeting that is scheduled for early afternoon - and yet Tony Conrad wakes that morning feeling a bit light headed and maybe nasally; a friend casually says it must be allergies - because they have them too - and, yada yada, bing bam boom, "you should take some Benadryl," it's recommended, "you'll feel fine in no time."

Three things about Tony you should know.

The first is, Tony doesn't really do drugs.  Not in his nature. Not for him. He drinks occasionally. Tony likes to be present and clear headed. So a whack of Benadryl may, say, have a bit more of a significant impact on him than someone who consistently whaps the dap or chases empathogenic molly vibes.

The second is Tony and I have a long history together, going back to 2005 or so; he was CEO of Sphere and something of a customer to my startup BzzAgent (the "Tony Mensch" story you can find elsewhere). Later, Tony backed us at previous True company Smarterer, and was instrumental and excellent at helping us deliver an incredible exit to Pluralsight. Net: Tony and I like to build things together.

The Founding of The Flipside, IV

Anyway, an hour or so before this particular Mylestone Board Meeting, Tony downs some Benadryl - this a syrupy concoction he's never, ever experienced before. It's only three of us in the Board Meeting; Jim and I hustle into the room ready to present our Mylestone Board deck, but also have our Flipside materials in our back pocket to share post-meeting. Were we nervous? You can bet your 2018-style side-strip trousers we were nervous.

The Founding of The Flipside, IV

A few slides in and we realize Tony and the Benadryl are having a moment. He discloses as such - that he doesn't take medicine of the sort and is feeling funny. And - as if to set a soundtrack to the meeting - it should also be noted that Tony has an apple, and a knife he's using to mostly slice off chunks but sometimes just sorta slap at the apple. All this very godfather style.

Dave, (nervous, slide 1): And so, blah blah, Mylestone's progress on revenue.

Tony (drowsy): Uh huh, and thwack thwack thwack goes the knife into the apple, as if drumbeat to our dread.

The Founding of The Flipside, IV

Then - suddenly! -Tony jolts awake; he stiffens upright and - get this - he lobs the knife across the room, as if exorcising the Benadryl demon. "What happened!?" he exclaims, "that was...wow...just really weird, and uncomfortable," he's remarking to us, but seemingly more to himself as he brushes himself off, adjusting his clothes, his scarf (Tony loves scarves) and seating posture.

The Founding of The Flipside, IV

At the end of the Mylestone meeting, Tony offers enthusiasm and motivational support for a business in its infancy:  "I really love all the progress here, very compelling." He wasn't wrong.

"Can we all say the Mylestone Board Meeting is complete," I begin?

And so Jim and I offer some sort of incoherent mish mash related to Flipside: "Tony, do you remember the Crypto Clubs I had mentioned a few months back? Well, they've sorta taken off, and we've been spending some time there and we really like what's happening and crypto is really interesting to us and there are so many smart people building cool things and the future of france and pepes and fidelity even has been doing work here for years and..." Tony is listening closely. You can see his gears turning. Jim is sweating. I'm sweating. Tony is staring.

We blabble on for another few minutes, walking Tony through some of our prepared slides, the sun slanting upon us through window slats, searing heat on our flushed skin. We're done. Toasted. We finish the last page. We've come clean, we've outed ourselves, we've provided relief to the lie we have been living.

The Founding of The Flipside, IV

Tony, with the slowness of a barn-owl hearing prey off in the distance, turns his head slowly, methodically to look at me. He stares:

"You," his pronunciation so clean and clear it's as if he's suddenly downed a handful of Piracetam Nootropics.

"You are a Papa Bear. You have built companies for years. You should know better than to do something like this." He's clearly steamed, maybe irate even. I've never seen him like this.

He turns to Jim, who is 15 years my junior and a bit earlier in his startup trajectory, "And You..." Jim is wide-eyed, readying for 10 lashings, or a bazooka, or fearful of the presence of the knife laying on the floor across the room, "You are a Baby Cub. Your career is just building and this is a terrible way to build your brand."

Here we sit, a Papa Bear and Baby Cub, standing with matches in the forest. The forest who happens to be none other than Tony Conrad.  Rightly so, he lights into us, he absolutely tears us apart about entrepreneurial commitment and spiritual authenticity. He isn't wrong, and we know it.

Tony finishes. He's rightfully delivered to us the essence of our malcontent, of our misbehavior and of our malevolence. Jim and I are well aware of the challenge we've created for True and for Mylestone shareholders, but also for Mylestone's hard-working employees. We are aware that Mylestone's potential may be limited - and we are aware of the huge opportunity for Flipside.

"So," Tony says calmly and matter of factly, a mature leader ready to get to solutions: "what exactly do you propose we do about all of this?"

And so we begin...

The Founding of The Flipside, Part V to follow...

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Dave Balter writes Mostly True Stories, a new one every Tuesday. He founded BzzAgent, Smarterer and Flipside, wrote Grapevine and The Humility Imperative, and is a venture partner at True Ventures.