This is going to be BIG.

MAY 4, 2022

For most founders, fundraising is a struggle. Only a small minority of people are born into the kinds of connections and life paths to provide them instant access to capital. The rest have to work super hard to create access for themselves, build trust and win investors over. That may come with the headwinds of bias working against you—conscious or otherwise.

founder 417

founder capital VC financing 417

This is going to be BIG.

APRIL 11, 2022

A few years ago, I was at Techcrunch Disrupt and this guy taps me on the shoulder as I was chatting in a group. He simply extended a handshake and said: “Hi, sorry to interrupt. My name is Alan. My company is Bread and we make ad creative super easy. I’m sending you an e-mail with early access to the application because I see that you’re busy with this group, but I just wanted you to match the name and the face.

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VC pitching communities investing 414

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

VC 391

VC founder ventures venture capital 391

This is going to be BIG.

OCTOBER 11, 2021

This is my daughter, Mirren. View this post on Instagram A post shared by Charlie O'Donnell - VC (@ceonyc) She’s the best. She was born 10 weeks early, on Labor Day, and like startups never are, has performed up and to the right nearly every single day that she’s been alive. We are incredibly lucky that she’s doing so well and we hope to have her home at the end of the month.

startup 186

startup investing investment VC 186

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 capital support education 195

This is going to be BIG.

JUNE 11, 2021

“The term 'residence' shall be deemed to mean that place where a person maintains a fixed, permanent and principal home and to which he, wherever temporarily located, always intends to return.” Putting aside the archaic gendering of the law, this one sentence written into New York State’s Election Law that defines the residency requirements of candidates is one of the laziest and most ridiculous pieces of text I’ve ever seen.

culture 284

culture real estate board opportunity 284

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.

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founder financing finance startup 397

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 support founder leadership 210

This is going to be BIG.

JANUARY 3, 2021

The other day, my wife Aja Singer and I were having a conversation about being more intentional with our time, especially when it comes to working. We both have multiple personal and professional projects that we’re involved with, and we felt like were getting sucked into spending time on things that weren’t moving these efforts forward—everything from too many meetings, or just getting sucked into social media rabbit holes.

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pitching board entrepreneurs media 300

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.

founder 545

founder VC startup coworking spaces 545

This is going to be BIG.

OCTOBER 18, 2020

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This is going to be BIG.

OCTOBER 12, 2020

I don’t really have a particular goal with this post. I’m just sharing. When I started leading deals at First Round Capital, I sourced investments in 8 companies. GroupMe, Singleplatform and Backupify all had really good exits, especially if you’re just looking at the multiples of the pre-seed/seed rounds, which is what I’m focused on now. I found GroupMe at the Techcrunch Disrupt Hackathon.

VC 367

VC investing investment founder 367

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 328

venture capital ventures VC capital 328

This is going to be BIG.

JUNE 1, 2020

I wrote this in my newsletter this morning: If you're not willing to ask yourself difficult questions, to be asked them, or to ask them of your teams, then this e-mail and, frankly, this "innovation" industry isn't for you. What have tech leaders been telling people they needed to do in order to be great founders and to build great things? Move fast and break things.

disruption 333

disruption support VC founder 333

This is going to be BIG.

APRIL 13, 2020

Obviously, the fight against Coronavirus has not stopped, but it’s hard not to look ahead to what’s next. How will having the world on lockdown affect our society in the long run? Here are a few trends I think we’ll see going forward: 1) Work from home is here to stay—at least partially. Absent the additional, albeit temporary, task of having to educate your own kids while at home, many people have reported being a lot more focused and productive while out of the office—not to mention the two ho

real estate 532

real estate creativity education media 532

This is going to be BIG.

APRIL 1, 2020

Let’s establish two things right off the bat: One, the Coronavirus Pandemic is a global tragedy that has already cost us far too many lives and create economic devastation. Two, if you are lucky, you are still being paid to do a job—a job that, for founders, marketers and sales teams, means connecting with customers during a terrible health crisis and a recession.

peer-to-peer 347

peer-to-peer ventures VC advice 347

This is going to be BIG.

FEBRUARY 24, 2020

The answer is easier than you thought: Anything you want. No, seriously—that’s the perk of running your own business. You select your salary. Now, if you want to have investors and potentially maximize growth for the company, that’s a different story. Investors are going to want their investment dollars to be going towards growth than going directly into your pocket—but what does that mean for how much you can actually pay yourself.

founder 302

founder startup capital investing 302

This is going to be BIG.

FEBRUARY 17, 2020

We’ve all heard the anecdotes—the famous founder who pitched 1000 investors before any of them said yes. That kind of story drives founders to take a “VC’s don’t know anything” approach to their business and trudge on despite legitimate criticisms of the business, often costing themselves tens of thousands of dollars or more of personal savings. So how do you know whether or not something is worth working on?

startup 294

startup pitching venture capital founder 294

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 367

pitching VC founder ventures 367

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.

capital 301

capital entrepreneurship sustainability education 301

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 252

venture capital ventures capital communities 252

This is going to be BIG.

SEPTEMBER 6, 2019

I got asked by a reporter yesterday what I thought about WeWork’s IPO situation and I’ll summarize what I said here: First off, let’s pull back for a moment and acknowledge that WeWork has built a huge company that generates a ton of value for its members. Real estate was previously a huge headache for small businesses before WeWork made co-working mainstream.

real estate 347

real estate disruption investing investment 347

This is going to be BIG.

JULY 14, 2019

“I didn’t want to bother you.” “I didn’t want to impose.” “I didn’t want to show up with my hand out.” “I feel like if you were interested, you would have said something already.” “I wasn’t sure if it was ok to ask.” “I haven’t spoken to that person in a while—it might be too random now.” Do any of these lines sound familiar? Too often, I meet founders that need something, and feel awkward about asking for it for a variety of reasons.

pitching 258

pitching venture capital founder ventures 258

This is going to be BIG.

MAY 20, 2019

Not every fundraise is easy and sometimes you wind up having to take a higher quantity of smaller checks than you’d like. On the other hand, some people try and pad the cap table with a bunch of big names or industry vets, even if their check size is small, just to build the network. They have an idealized vision of how easy it’s going to be to utilize everyone once the business gets going.

founder 287

founder startup networking capital 287

This is going to be BIG.

APRIL 7, 2019

Over the years, we’ve seen a revolution in how labor is supplied because of technology. First, we saw simple outsourcing—taking one person doing one job and moving the job over to a cheaper person in another geography. That only worked because you could connect everyone via technology—routing phonecalls, e-mails, design documents, etc. halfway across the world so that working with someone in India was as seamless as if they were on another floor in your building.

technology 240

technology startup construction founder 240

This is going to be BIG.

MARCH 14, 2019

Some VCs peel off of other funds to start their own and they have the benefit of a track record from their previous firm to show. Obviously, that’s ideal, but that’s not where everyone starts. If you’re lacking for track record as a firm, here’s three exercises you should walk through to help turn your pitch and due diligence meetings from guesswork into something more substantive.

ventures 282

ventures angel investing VC investing 282

This is going to be BIG.

MARCH 3, 2019

You hear this from VC’s a lot: “We need to own X% of your company to make our returns.” They back it up with sensible math—owning 20% of a billion dollar outcome returns a $200mm VC fund, and, of course, you’re trying to at least return the fund. So, no one really questions the ownership model. Yet, when you buy shares of Apple or Facebook, you don’t even think about what percent of the company you own.

VC 276

VC capital investing investment 276

This is going to be BIG.

FEBRUARY 25, 2019

The other day, I generated a lot of buzz and feedback around my assertion that calling yourself an “angel investor” should require a little more than small syndicate investments: You are not an angel investor if all your investments are less than $10k, made through @AngelList syndicates, and the founder doesn't even know who you are because you've never met.

VC 275

VC founder ventures venture capital 275

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.

founder 287

founder financing finance capital 287

This is going to be BIG.

SEPTEMBER 12, 2018

Whether you’re going through an accelerator or you’re at some kind of speed dating event, short “office hours” meetings present both an opportunity and a problem for investors. It’s a great way to get out from behind the e-mail and actually meet people face to face. However, it’s a terrible way to get your whole pitch in. There’s just not enough time to convince someone to invest and have a productive back and forth.

pitching 247

pitching SaaS ventures accelerator 247

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 188

networking frameworks enablement communities 188

This is going to be BIG.

JUNE 17, 2018

Powered by OpenReel Building a relationship with an investor, someone who is drowning in pitches and requests for their time, can be difficult. How do you cut through the noise? In this video, I share three ideas for kicking off a relationship with an investor you don't know.

venture capital 201

venture capital ventures capital pitching 201

This is going to be BIG.

JUNE 11, 2018

Time and time again, I hear how hard of a time startups are having recruiting, especially for software developers. While candidate quality is sometimes an issue, or culture fit, or some other quality, most of the time the issue is that the company just isn't getting enough people into the top of the funnel. When I was a startup founder, I had this same issue.

startup founder 316

startup founder startup ventures founder 316

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.

VC 265

VC founder culture education 265

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 326

board advice founder networking 326

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?

board 188

board strategy investing investment 188

This is going to be BIG.

JANUARY 8, 2018

I've rewritten a lot of pitch decks over time and a lot of them are really bad--mostly because founders have been told what should go in them without a lot of consideration as to why. Somewhere along the line, someone came up with things that are supposed to go in a pitch without ever asking investors how they take in a story. Here what I want to see in the video below.

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pitching VC startup founder 354