A lot of peo­ple ask me why I wrote my first busi­ness book, NightLife Lessons. The answer is sim­ple: it was most­ly a buck­et list item for me, and not about mak­ing mon­ey. Sure, I want­ed to help myself by look­ing back and writ­ing down what I’ve learned over the years, in the hopes of help­ing oth­er start­up entre­pre­neurs on their jour­neys. But for the most part, I just want­ed to see if I could write a book…and then hold it in my hands. Below, I’ll share a bit about the process of writ­ing my book and what it was like for me.

Telling Sto­ries

I’ve been fund­ing and advis­ing start­up founders and entre­pre­neurs for almost a decade now. As part of that role, I often find myself telling sto­ries from my own expe­ri­ences build­ing star­tups, to help founders not only deal with their cur­rent strug­gles, but also avoid pit­falls that might lie ahead of them. 

I’ve been told that what sets me apart is that while oth­er VCs just write checks, I share valu­able, first-hand infor­ma­tion gath­ered from ups and downs I’ve expe­ri­enced as a fel­low founder. 

This is part­ly what inspired me to get start­ed on NightLife Lessons. I decid­ed it was final­ly time to com­pile these sto­ries into a book and make it acces­si­ble to every­one. So, I spent the last two years pack­ing the man­u­script with the most valu­able and poignant lessons I learned from one of my first star­tups back in 2001: JoonBug.

Down to Business

It took me almost a year and a half to write the first draft. Dur­ing that time, I had to go back and basi­cal­ly research my own life, dig­ging up pho­tos and recon­nect­ing with old friends and col­leagues, in order to remem­ber all of the details and events from the Joon­Bug days. It was quite the trip down mem­o­ry lane!

There were def­i­nite­ly ups and downs along the way. Some days, the words flowed out of me like water from a faucet, and I felt like I could­n’t type fast enough to keep up with my rac­ing thoughts. Oth­er days, I stared at the blank screen for hours on end, feel­ing com­plete­ly uninspired.

But in the end, I did it! I wrote a book that tells the sto­ry of my entre­pre­neur­ial jour­ney through the lens of all the crazy (and some­times hilar­i­ous) things that hap­pened to me dur­ing my years work­ing in nightlife. 

From anec­dotes about famous celebri­ties to sto­ries about times when things went hilar­i­ous­ly wrong, NightLife Lessons has it all.

Not Your Typ­i­cal Busi­ness Book

As you can imag­ine, a busi­ness book that revolves around the nightlife indus­try is a lit­tle … dif­fer­ent. The set­ting is New York City’s night­club scene in the 90’s, when Club Kids, musi­cians, and artists rubbed elbows with aver­age Joe’s, drag queens, and mod­els in icon­ic clubs with essen­tial­ly no rules (oth­er than those imposed at ran­dom by all-pow­er­ful doormen).

This was one of the most unlike­ly indus­tries for any­one to build a tech com­pa­ny around. Espe­cial­ly since this was also right around the time that the infa­mous 2000’s tech bub­ble burst, and just after 9/11 in NYC; a time when the gen­er­al mood and sen­ti­ment in the coun­try was very somber. 

It was an uncer­tain, dif­fi­cult time and place to start any busi­ness — let alone one that merged tech and nightlife in ways that were com­plete­ly new and out­side the box.

This book dives deep into the obsta­cles and fail­ures I endured while boot­strap­ping my own tech start­up in an unfor­giv­ing, fick­le indus­try resis­tant to change. It shares insight­ful sto­ries that illus­trate lessons that I learned the hard way.

I explain my thought process and men­tal mod­els about solv­ing prob­lems, sell­ing myself and my busi­ness, and iden­ti­fy­ing oppor­tu­ni­ties that nobody else could see.

I also explain how I used these lessons in my sub­se­quent suc­cess­ful ven­tures, and in my invest­ing career.

Of course, along the way, my aim is to have read­ers enter­tained, shocked and laugh­ing out loud!

Lessons Learned

So what kind of lessons does NightLife Lessons aim to teach? To name a few:

• Fake It ​‘Til You Make It: How did Joon­Bug land its first event at an ultra-luxe, exclu­sive venue with no mon­ey and no expe­ri­ence? Some­times, the only way to get start­ed is to fake it until you make it. And there’s noth­ing wrong with that. After all, every­body is a nobody until they con­vince oth­ers (and them­selves) that they are somebody.
• Murphy’s Law: What­ev­er can go wrong, will go wrong, so expect it and deter­mine to be resilient when (not if) it hap­pens. If you have the mind­set of being flex­i­ble and bounc­ing back no mat­ter what the cir­cum­stances, then you have what it takes to suc­ceed in any business.
• Fol­low Your Pas­sions: Not blind­ly or lazi­ly, but per­sis­tent­ly. Be in search of nov­el­ty and your pas­sion instead of a rigid objec­tive. I start­ed out with a hard-won spot at NYU Med, deter­mined to become a doc­tor. But along the way, it became increas­ing­ly clear that this wasn’t the right path for me. Mean­while, my grow­ing pas­sion for tech­nol­o­gy led to my start­ing a tra­di­tion­al tech com­pa­ny — that failed after the dot-com bust. From there, I final­ly found suc­cess in the nightlife indus­try. The only way that can hap­pen is by trust­ing and fol­low­ing the step­ping stones that show you suc­cess in life, no mat­ter how unpre­dictable they may be.
• The Par­ty Always Comes to an End: Know­ing when it’s time to stop and move on is just as impor­tant as know­ing when it’s time to start some­thing new. 

Val­ue Proposition

So who is NightLife Lessons for? I wrote this book for any­one just start­ing out in busi­ness; any entre­pre­neur, whether they are going through a dif­fi­cult peri­od or a bril­liant burst of success.

Addi­tion­al­ly, any­one who is in the nightlife or hos­pi­tal­i­ty busi­ness would ben­e­fit from read­ing about what it was like trans­form­ing the indus­try from an ana­log, pre-face­book, cam­era-phone era to the dig­i­tal age. I also dive into how I think the next gen­er­a­tion of tech will con­tin­ue to trans­form the indus­try, from the Meta­verse and beyond.

Write On

As a final word, I want to say that writ­ing this busi­ness book has been a huge­ly reward­ing project. If you’re an entre­pre­neur who is think­ing about writ­ing a book, I say go for it! It’s an incred­i­bly engross­ing expe­ri­ence… even if it does take some time and effort to com­plete it. Trust me, it’s worth it. Who knows? You might even find your­self hold­ing your own book one day soon.

Orig­i­nal­ly pub­lished on Shane Neman’s web­site on Decem­ber 30 2022.