This is going to be BIG.

JANUARY 8, 2023

Prompt: “A Cartoon Teacher being crushed by the weight of society’s problems” - Stable Diffusion 2.1. This past Tuesday, New York City's Department of Education announced a ban on the popular chatbot ChatGPT from its schools' devices and networks. It’s easy to understand why. The bot can write essays instantaneously, opening up a pandora’s box of ways to cheat, right?

technology 385

technology education networking leadership 385

This is going to be BIG.

DECEMBER 5, 2022

These are the first marketing images of an upcoming movie that I star in with my daughter Mirren about an aging superhero that is absolutely too old for this s**t that winds up having to save some mystical star child. Or, it’s just what “generative AI” does with a series of uploaded images of the two of us if given some creative prompting. Enthusiasts will tell you that this is the beginning of being able to insert yourself into video games, recreate scenes of things that happen to you in the pa

creativity 243

creativity media enablement collaboration 243

This is going to be BIG.

AUGUST 1, 2022

Recruiting is hard. Good candidates are hard to find. What tells you this? Well, you can see it. Out of all the candidates that applied to your job post, very few are what you’re looking for and those that are seem to be falling down in the interview. I hear it all the time—and when I hear it, I hear a red flag. Did you hear it? “Applying to our job post.

leadership 221

leadership networking development founder 221

This is going to be BIG.

MAY 24, 2022

If you’re out raising, it’s quite normal for you to peer over the fence and see how far other founders are getting at the same stage. The most obvious attribute for comparison is stage—have they launched, do they have paying customers, etc. Unfortunately, this is a fundamental misunderstanding of how startups raise. Fundraising is not a reward for the past.

peer-to-peer 243

peer-to-peer startup VC pitching 243

This is going to be BIG.

MAY 9, 2022

I’ve been asked by portfolio companies and plenty of others about how they should be changing their strategy given the stock market pullback and what they’ve been hearing on “VC twitter”. My answer depends on whether the company would answer yes to any of the following questions: 1) Did you raise an overpriced round in the last 18 months—one you know was over the top?

VC 243

VC financing finance leadership 243

This is going to be BIG.

APRIL 13, 2022

Whenever I submit a term sheet, I always caveat it by saying the following: “This is the one time we’re completely misaligned. I’m incentivized to buy up as much of the company at as low a price as possible and you’re incentivized to sell as little of the company as possible by raising the price.”. Founders seem to get that. The price negotiation process is pretty straightforward, and once a deal has been agreed upon we move on.

founder 398

founder VC board strategy 398

This is going to be BIG.

FEBRUARY 27, 2022

Someone asked me yesterday whether or not I would ever consider living anywhere else. For years, family was the main consideration for me concerning location. My family is based in New York. My mom had a long chronic illness before she died and my grandmother lived past 100. Being here for my family was priority one. Besides, there were a limited number of places where I could do my job in venture capital anyway—and while I might be a go to for a pitch from super early stage pre-seed and seed fo

culture 320

culture VC communities education 320

This is going to be BIG.

NOVEMBER 28, 2021

After 80 long days in the NICU, my 10 week early daughter Mirren has finally come home. We’re overjoyed and we’ve begun the task of learning how to manage all the logistics of her care—while somehow doing the bare minimum of that for ourselves. We both showered in the last 24 hours, which is a major moral victory for the team. TFW you’re small and slippery and you realize your parents have no idea how to give you a bath.

hospitality 449

hospitality board energy collaboration 449

This is going to be BIG.

JULY 29, 2021

The science is clear… and so are the economics. Vaccines prevent the spread and severity of the COVID-19 virus with side effect rates at well below the instance levels of lots of other drugs people commonly take for things like birth control, erectile dysfunction or to keep their cholesterol in check. Yet, somehow, things like masks and vaccines have become a political hot potato—dividing the country in two on how to avoid a four (fifth?

hospitality 195

hospitality education support technology 195

This is going to be BIG.

MARCH 28, 2021

A lot is made out of the price of a round. It’s the one time that, as an investor, I’m not aligned with the founder at all. I want to try to buy up shares of the company as cheaply as possible (and own more) and the founder wants to give up as little of the company as possible. That all being said, I’ve yet to meet a founder that sold their company for $100 million or more who looks back with great regret at the price they raised their seed round at.

founder 332

founder financing finance startup 332

This is going to be BIG.

JANUARY 24, 2021

The other day, I was talking to a highly experienced female professional out raising money. It was super clear to me that she was incredibly qualified to tackle the problems that she was raising money to go after—but few people in the ecosystem knew who she was compared to other, more high profile professionals. There were other people who spend more time on social, doing the podcasts, videos and interviews—things that, while brand building, opened them up to more criticism.

media 210

media leadership support communities 210

This is going to be BIG.

DECEMBER 3, 2020

Fund investing, like adulting, is boring. That’s the first thing anyone trying to raise a fund needs to understand, as well as anyone thinking about investing in one. The partner at the fund, the VC, gets to do the fun part—the meeting with founders, vetting deals, negotiating, helping, etc. You get, if you’re lucky, a Powerpoint and some financials once a quarter.

VC 335

VC angel investing mix-use opportunity 335

This is going to be BIG.

NOVEMBER 15, 2020

In February of 2017, Susan Fowler’s description of the pervasive cultural issues at Uber, after the company’s abject failure to address her sexual harassment complaints properly, finally broke through in a way that garnered the tech community’s appropriate attention. The company’s bad behavior was nothing new. Just weeks before, Uber was fined $20 million for recruiting drivers while publicly exaggerating claims of their earnings potential.

coworking spaces 541

coworking spaces hospitality culture coworking 541

This is going to be BIG.

AUGUST 30, 2020

Talk to ten founders and ten different VCs and you’ll get roughly about 600 different suggestions as to how you should go about your fundraising strategy. I don’t know what the formula is here, but the numbers and the resulting amount of confusion gets big very very quickly. Why does it seem like there’s an exception to every rule? You’re told that you can’t raise until you have a product, yet pre-product companies get funded all the time.

strategy 379

strategy real estate pitching startup 379

This is going to be BIG.

JUNE 15, 2020

There have been a lot of calls for VC firms to make more hires from the Black and Brown community, as well as to hire more women. Not all hires, however, are made equally. In venture, it’s all about getting an opportunity to make partner and being included in the carry—the economic upside of a fund. Not only is carry a means of economic mobility, but it’s also a reflection of where decision-making authority is within a fund.

venture capital 305

venture capital ventures capital mentorship 305

This is going to be BIG.

FEBRUARY 20, 2020

As a founder, your most valuable asset is your time—and there is probably no group of founders who are more efficient about getting the most out of their time than moms. Moms also have a unique and personal insight into what’s important to other moms when they buy things for their kids. They’re looking for products that save time, provide good value, are good for their kids and have values they believe in.

ventures 334

ventures pitching founder development 334

This is going to be BIG.

FEBRUARY 3, 2020

I see this time and time again—a founder pitches a VC or an angel and they say to come back when there’s more traction. The founder then goes off and raises from friends and family or invests their own savings in the idea in an attempt to come back with a handful of customer or users. In other words, the people with the least amount of money in this game wind up doubling down on what is probably an unfundable, problematic idea to begin with—because an investor said the only thing missing was tra

pitching 340

pitching VC opportunity founder 340

This is going to be BIG.

JANUARY 27, 2020

Every election cycle, you hear the same thing—Republicans are good for the economy and electing a liberal will tank it. This is especially the case this time around as we’re in the middle of the longest running expansion this country has ever seen—and no one wants the other shoe to drop. There’s a lot of fear that making the wrong choice will mess things up.

education 262

education sustainability transportation opportunity 262

This is going to be BIG.

DECEMBER 5, 2019

There’s one thing that no one can ever take away from Adam Neumann—he was world class at fundraising. His ability to tell a story and gain investor confidence was unmatched relative to the underlying progress of the company. He exuded confidence told people he was going to change the world. It’s not actually surprising that investors bought into it, considering that for a long time, VCs have focused on one particular archtype of leader as being more worthy of venture investment than others—the b

founder 153

founder pitching leadership culture 153

This is going to be BIG.

DECEMBER 4, 2019

A lot is made of the best practices around raising capital—but I think a lot of the advice is a bit too clever. First off, most of it is parroted by people who never raised any money. They’ll come up with a lot of reasons why raises didn’t happen, like “The round fell apart because it was too close to the holidays.” No one ever says, “My idea wasn’t good enough and that’s why we didn’t raise.

venture capital 153

venture capital ventures capital pitching 153

This is going to be BIG.

SEPTEMBER 18, 2019

I believe that the next generation of top companies are far more likely to be founded by people not on VC radars today. Today's top founders will undoubtedly start something new in the future, but they won't make up the majority of innovators going forward--just as prior generations of venture backed founders don't make up a majority of those who are succeeding today.

venture capital 235

venture capital communities ventures capital 235

This is going to be BIG.

JUNE 14, 2019

I’m getting married today. At least, if she says yes. But, assuming that all goes according to plan, I have a few thoughts on how I got here—given that dating and relationships seem to vex a lot of people. I would say that the most important factor that went into both of us finding someone to marry was that neither one of us felt like we had to find someone to marry to be content.

development 379

development 379

This is going to be BIG.

MARCH 19, 2019

I'm a bit tired of tweeting, donating, protesting, etc. to end gun violence--so I'll take a different tact in the wake of the Christchurch shooting. If you're an investor, employee, or just user of a large media distribution network, please ask the hard questions about the responsibilities of those platforms to prevent the spread of hate and violence--again and again until these platforms take their role seriously.

media 356

media networking innovation 356

This is going to be BIG.

MARCH 18, 2019

Across the world, various economic development organizations, government agencies, and non-profits are putting in admirable and well-intentioned efforts to develop startup ecosystems. They’re building campuses, districts, buildings, spaces, as well as running new educational efforts and contests—basically anything they can think of to foster the growth of new and innovative companies.

startup ecosystem 310

startup ecosystem real estate startup economic development 310

This is going to be BIG.

FEBRUARY 21, 2019

While most of the money that goes into VC funds comes from institutions that are highly experienced in the asset class, some family offices and high net worth individuals also invest in VC. They’re trying to get exposure and diversification at the same time, while potentially seeing co-investment deal flow. A lot of VC fund pitches—and I know this because I used to vet VCs for a living as an institutional limited partner at a pension fund—sound the same.

VC 267

VC investing investment strategy 267

This is going to be BIG.

FEBRUARY 20, 2019

The headlines in the tech and startup world have not been good over the last couple of years. As it turns out, the “move fast in break things” culture was itself pretty broken—full of discrimination and harassment. On top of that, the rise of tech is exacerbating wealth inequality, creating some serious data privacy issues, and allowing hate and misinformation to grow rampant on its platforms.

transportation 295

transportation education construction culture 295

This is going to be BIG.

NOVEMBER 4, 2018

For the last two years, I’ve been pretty vocal about politics on social media , in my weekly tech community newsletter and on this blog. As I’ve gotten older, I’ve gotten more progressive—which is a big shift for me because I grew up conservative. More and more, I’ve felt the need to speak out—but the question was asked of me recently whether or not it does more harm than good for me professionally.

investing 244

investing investment communities founder 244

This is going to be BIG.

SEPTEMBER 25, 2018

I started a company back in late 2007. We raised $550k in seed funding and, despite a lot of hard work, things didn’t work out. It turned out I wasn’t such a great product manager, the technical things we were doing were about two years too early—about to be made orders of magnitude easier by a lot of cloud and big data tools, and, oh, yeah, Lehman went under when I was pitching VCs for money in 2008.

financing 269

financing finance pitching founder 269

This is going to be BIG.

JULY 30, 2018

Decided to follow no more than 250 people on Twitter. If you got bumped, blame @willyf , who just made a good case for me to follow him. :) — Charlie O'Donnell (@ceonyc) June 30, 2008. Just about 10 years ago, I tried hard to keep my Twitter follows to a manageable amount--to people I actually cared about following and either already knew or wanted to get to know in person. 5000+ follows later and I've failed miserably.

networking 157

networking frameworks enablement media 157

This is going to be BIG.

JULY 9, 2018

Recently, I helped one of my portfolio companies make a VP of Marketing hire. The founder asked me early in the process if I thought the candidate was good. Having not worked with her previously, I didn't know how talented she was firsthand, but what I did have confidence in was that her strategy would be well thought out, and if it wasn't working, she'd analyze why, proactively address it, and describe what steps she would take to find a solution.

media 215

media strategy communities founder 215

This is going to be BIG.

JUNE 3, 2018

I was talking to another investor the other day about the stress that surrounds the ups and downs of the job--winning and losing deals, and having some companies succeed versus others going south on you. I shared with this VC my secret to keeping stress at bay: I concede the fact that the possibility exists that I'm not good at this. My fund performance is positive and things seem to be going in the right direction--I've been fortunate enough to back a lot of interesting companies--but there's a

health 203

health VC 203

This is going to be BIG.

APRIL 23, 2018

A few weeks ago, I booked a customized tour of Iceland with Noken , and I did it in about five minutes. All I had to do was to tell Noken how long I planned to go, what level of hotel and car I wanted, and then I had the option to add on a few extras, and within minutes my entire trip was booked. I had a connection to my own personal trip concierge and a custom app that outlined my trip.

culture 223

culture education VC opportunity 223

This is going to be BIG.

APRIL 9, 2018

It's really hard to advise a company when you don't have all the information--and no one has more information than the CEO of the company. Sometimes, you might believe the CEO is ill-informed, and you're a check on the amount of homework they've done to seek out solutions to a problem, or which metrics or signals they're paying close enough attention to.

board 273

board advice strategy networking 273

This is going to be BIG.

FEBRUARY 25, 2018

In the last couple of weeks, I've had two similar conversations with my portfolio companies. They were just starting to build out their marketing strategy and they were faced with the challenge of how to staff it. Do you hire someone senior who might feel like the execution of the work was beneath them--or who simply hadn't done it in a while? Or, do you hire someone adept at the actual creation piece, but who needed guidance around how things were strategically put together at a high level?

strategy 157

strategy board investing investment 157

This is going to be BIG.

JANUARY 22, 2018

Last week, on Martin Luther King Day, I decided that instead of saying something in my weekly newsletter , I would do the opposite--I would listen. I asked, "What is your experience of being be black in tech today and what can allies do to improve it?" The responses I got came at a time when I've been having a lot of conversations with female founders as well about their fundraising experiences.

VC 251

VC pitching peer-to-peer founder 251

This is going to be BIG.

JANUARY 1, 2018

Year after year, educators and those invested in education love to speculate about what will take off in the near future. And as far as riveting news goes, nothing quite peaks the interest like new trends that have the potential to fundamentally change learning. In almost all of the commentary from both educators and industry, the mention of AR and VR for 2018’s big trends were ubiquitous.

education 400

education media investing investment 400

This is going to be BIG.

DECEMBER 21, 2017

Board meetings at @amplehills are dangerous. A post shared by Charlie O'Donnell (@ceonyc) on Dec 20, 2017 at 8:06am PST When you're Ample Hills Creamery , the #1 rated ice cream shop in the country you can pretty much throw everything you've been told about fundraising out the window. Nothing seems to apply--you're not a tech company, you bootstrapped your way to millions in revenues before taking on capital, and you sell mostly through brick and mortar.

pitching 226

pitching VC strategy investing 226