grieving is a weird thing. it’s probably in the top 3 of most primal and intense feelings we can have as human beings, but it’s the only one that is always bad. for example, when you fall in love, it’s a good thing but can be a bad thing for any number of reasons.

when you feel grief, it’s most certainly not because something positive happened.

everyone deals with it differently, some not dealing with it at all. i was in the latter category for a number of years. anyone who defers dealing with something bad, like a death, ends…


quite honestly, the question “what’s next?” is an exhausting game, albeit fun. it has driven my life since i can remember.

i’ve been working since i was 14. i always saw work as an adventure and not so much as a career. i dropped out of high school in my senior year when i was 15 because i realllllllllllly liked moving needles at work. and maybe i liked proving things to people.

i’ve moved a lot of needles.

work has been both good and bad to me. however, anything you lose yourself in completely probably isn’t a good idea for long stretches, i’ve learned. during both…


new investment model, who dis.

almost three years ago when scaleworks reached out to me and told me about their model i was simultaneously intrigued and extremely skeptical.

skeptical because when i was a writer at techcrunch, if a SaaS company that had actual revenue (gasp!) got into my inbox, i’d usually a) sigh in “disgust” and b) forward it to ron miller.

in fact, the first dm i ever received from my (now) wife (while i was a reporter) was about an invite to oracle openworld.

i’m lucky that i was able to recover from this.

i didn’t go. because once again. enterprise and…


thanks for reading the last one, i got a few really really good questions and the topic that keeps coming up on re-entry is “when is the right time?” and “is it ok if it takes me longer than others?”

in short, there is no right time and yes it’s ok if it takes you longer to feel comfortable and/or adapt to heading back out in public and work, etc. no state has shared a fully-baked plan. the white house’s phase approach actually is a nice framework.

here’s the deal: there is no “switch” that’s going to flip that makes…


this is probably part 1 of some number of posts. bear with me here, this is hard to talk about. this part is more of a set-up. we’ll get to nuts and bolts another time.

i want to preface all of this by saying not everyone is the same. not every situation is the same. if you are currently quarantined in a dangerous and abusive situation, please check out some resources. you do not deserve this treatment.

ok.


My Tumblr was hacked a long time ago, so I grabbed an archive of this post.

That’s not what I ordered…

…Can I send it back?

That’s exactly what I wanted to say. I had about 10 really smartass things to say back. But I couldn’t. I was frozen. Speechless.

Zip back a few weeks. I had parted ways with Strands, and got the most amazing opportunity with GOGII in LA as Director of Community. Dream job.

A move to LA was imminent. But first, a trip home to Philly to visit the folks and friends on the east coast. I hadn’t gotten to see them much.

I noticed a lump on my neck. Not huge…


one day you’re a founder at a vc firm, the next you’re writing a post like this.

clearly, it’s a topic close to me and to many of you. things seem to be humming along quite nicely and then you or someone that you know and love gets the call.

“cancer.” (or insert other awful thing)

waiting for a diagnosis is like tick-tick-ticking up a rollercoaster and once you hear the confirmation, you’re tossed over the top for the craziest, most awful ride of your life.

that’s why, when i read ben’s post about him and his partner grace, who…


so if you’re into tech, you’ve probably read about facebook and lime using a communications firm called definers public affairs.

tldr they’re a low-rent firm taking advantage of the paranoia that is super pervasive in silicon valley. there’s been a rush of these types heading to the valley ever since trump took office. all bets are off. all tactics are welcome. and it’s no different than hiring a “growth hacker” or an “seo expert”. immediate gains with potential long term damage. but hey, ¯\_(ツ)_/¯.

this particular firm worked on romney’s presidential campaign and other political projects…a land where…


tl:dr i’m joining the phifth quarter to feed my appreciation for the sixers.

so i’m a kid who basically knows nothing about nothing and i said to my coworkers and friends, “yo, let’s start a podcast.” they looked at me like i had eight heads. in my mind, we talked about tech all day, so it totally made sense.

we called it “the best damn tech show, period.”

this was more than 12 years ago. we had a blast. wasn’t a full time thing. it was for fun. we met a lot of great people. more importantly, paul, adam and…


where do i start? well. as it seems, or feels, i’ve gotten to go through some really tough patches in life that a lot of other folks have gone through. but it always seems like it came with a wrinkle.

parents divorced when i was young. my dad was a cop. he had to retire due to stress on the job. that came by way of being diagnosed as a paranoid schizophrenic. he put a gun to my mother’s head and we were out of there.

my mom was young, she wasn’t ready to enter the workforce, so we lived…

drew olanoff

troubadour.

Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store