A VC: Musings of a VC in NYC

JULY 27, 2021

Our 2008 vintage early-stage fund has generated about 5x cash on cash but only generated a 22.5% That explains why our 2010 Opportunity Fund has a lower cash on cash return but a much higher IRR than our 2008 early-stage fund. Three of our most mature funds showcase how these numbers can behave differently.

opportunity 279

opportunity venture capital strategy investment 279

Dream It

APRIL 7, 2020

Since 2008, Dreamit has worked with over 350 companies. Dreamit works with top healthcare, cybersecurity, and urban technology startups, providing access to extensive customer, industry, and investor networks during its 14-week program.

ventures 369

ventures accelerator enablement communities 369

Both Sides of the Table

SEPTEMBER 12, 2013

He first came to see me in 2008 when we was raising money for his 1st startup – NextMedium. At every entrepreneur event I through between 2008-2012 I invite Hamet because he was a great mentor for entrepreneurs. I’ve known Hamet for 5 years. It doesn’t take a rocket scientist to see the problems in this structure.

ventures 340

ventures investment investing board 340

Both Sides of the Table

OCTOBER 14, 2015

We have an entire generation of startup founders who don’t have muscle memory from getting their burn rates back into shape from 2008/09 or 2001-2005. Some companies have to go first. Others will follow. But many of us have been there. It’s not fun. But it’s necessary.

VC 392

VC capital culture venture capital 392

Both Sides of the Table

JUNE 27, 2013

We have previously raised funds in 1996 ($200 million), 2000 ($400 million) and 2008/9 ($200 million). I am super excited to announce that today is a day of lots of new things for my partners & me: A new fund, a new office and a new brand. Let’s start with the fund. This month we closed our 4th fund of $200 million.

ventures 343

ventures venture capital advice VC 343

Both Sides of the Table

AUGUST 24, 2015

I’ve seen friends (and family members) lose much of their savings that way over the years because “Black Swans” happen and in 1987, 2001, 2003 & 2008 (just to name a few from my memory) huge market gyrations caused much financial distress to people seeking short-term gains. Watch the market closely.

finance 344

finance financing ventures real estate 344

This is going to be BIG.

NOVEMBER 6, 2013

In fact, much of the groundwork of the NYC tech community''s growth came before the late 2008 economic crash--when the city started paying attention to the tech community as the economic savior poster child. The multifold growth we''ve had in the startup engineering base of NYC happened before we even decided to build these companies.

education 317

education venture capital communities ventures 317

Tomasz Tunguz

JULY 4, 2020

We reviewed the data in May and compared it to the effects of the financial crisis in 2008 on startup fundraising. As a reminder, 2008 saw a 40% reduction in venture dollars invested in startups. These corrections match 2008. It took about six to eight quarters to return to normalcy. But the patterns this time are different.

collaboration 145

collaboration accelerator capital investment 145

Entrepreneurs' Organization

DECEMBER 1, 2021

Working in wine during the financial crisis of 2008, I quickly noticed the opportunity to innovate within the alcohol logistics industry alongside my business colleague, Tim Elenteny. These experiences taught me that I possessed excellent interpersonal skills and demonstrated talent in sales and marketing.

hospitality 268

hospitality leadership collaboration entrepreneurship 268

This is going to be BIG.

JUNE 8, 2014

Even the old Pfizer headquarters, active as recently as 2008, is now home to the production of everything from microchips to pickles. Refactory is trying to create an end to end process from design to manufacturing for hardware on Sackett Street.

mix-use 329

mix-use communities venture capital creativity 329

This is going to be BIG.

FEBRUARY 17, 2014

In 2008, I went to breakfast with Hilary Mason while I was down there. We just hung out in a small group of nobodies, having chatted a bit through our respective blogs before. In fact, as I look through the photos from back then, I realize that I funded two nobodies from that group--the other being Michael Galpert at Super.cc.

communities 327

communities VC accelerator startup 327

Dream It

APRIL 12, 2020

LPs failed to make capital calls in the late 90s during the dot-com bubble burst, after September 11, and during the financial crisis in 2008. In 2008-2009, the financial markets seized up, and there were quarters of complete uncertainty, but ultimately VCs started investing again and things normalized. This is not without precedent.

ventures 334

ventures startup capital board 334

Both Sides of the Table

MARCH 6, 2016

In 2008 I started VC blogging. They thought it was like MySpace and why did I need a MySpace page? In 2007 I started using Twitter and most of my friends & colleagues wondered why people would care what I ate for lunch. I had blogged when I was an entrepreneur. Ironic to be self-centered while you’re trying to offer advice to others.

networking 230

networking advice VC financing 230

Both Sides of the Table

MARCH 24, 2014

I spent my first year developing proprietary deal flow and learning the business and then the Sept 2008 / Lehman Bros collapse / financial meltdown happened. I become a venture capitalist in September 2007 – exactly 6.5 years ago. That company was Invoca, which just announced a $20 million fund raise led by Accel.

VC 387

VC venture capital ventures financing 387

Entrepreneurs' Organization

MAY 6, 2020

Others recall the 2008 financial crisis. “You’ve probably never felt anything like this,” Rustand says. But we’ve all dealt with things that felt new and terrible at the time. Some of us remember the 2000 dot-com crash. In terms of pandemics, we remember avian flu (1997), SARS (2003) and MERS (2012).

advice 274

advice transportation leadership entrepreneurs 274

Both Sides of the Table

JULY 29, 2015

I saw this in 2001-2003 and in 2008-2010. You find out those that have the fortitude to work out a new way forward, who can handle recapitalizations or downsizing or shutting down business lines or hiring whole new teams.

creativity 378

creativity culture entrepreneurs energy 378

American Entrepreneurship

JUNE 10, 2025

Brian Chesky (Airbnb): Launched during the 2008 recession, faced legal battles, trust issues, and scaling challenges—but persisted through relentless adaptation. Melanie Perkins (Canva): Faced years of rejection and multiple product iterations before Canva gained traction—and eventually became a unicorn.

entrepreneurship 87

entrepreneurship peer-to-peer entrepreneurs enablement 87

Tomasz Tunguz

MARCH 11, 2020

The most recent event to use as an analogy is the 2008 financial crisis. In 2008, I had just joined the venture industry, and then Lehman fell. That grew to about $5B per quarter in 2007 and early 2008. Seed investments suffered a 50% fall in Q3 2008, but the market came right back in Q4 and continued to increase in volume.

ventures 143

ventures VC investment investing 143

Both Sides of the Table

JANUARY 2, 2014

It follows on from the equally compelling “ Game Change ” by the same authers, which I read years ago after the 2008 election. It is politics, relationships, money-grabbing and especially power-grabbing human behavior at it’s peak.

startup 385

startup coworking advice leadership 385

Entrepreneurs' Organization

JULY 6, 2020

Like the downturns in 2008 and 2001, this has been a very trying time for entrepreneurs running startups. Contributed by Rizwan Virk , author of S tartup Myths and Models: What You Won’t Learn in Business School. The pandemic of 2020 has tested most sectors of the economy.

peer-to-peer 321

peer-to-peer startup advice entrepreneurs 321

Both Sides of the Table

JUNE 1, 2011

years ago you’d remember RIP Good Times from Sequoia, which still strikes me as having been prudent advice in late 2008. .&# That’s how it felt then and a bit how it feels in May 2011. If you were reading the headlines from only 2.5 So which is it? Feast or famine? Bull or bear? As a market we seem to be incapable of temperance.

advice 391

advice VC financing finance 391

Dream It

JANUARY 23, 2019

Since its founding in 2008, Dreamit has accelerated nearly 300 startups, including LevelUp (acquired by GrubHub), Trendkite (acquired by Cision), SeatGeek, HouseParty, Adaptly (acquired by Accenture), Wellth, Biomeme, Tissue Analytics, Redox, Eko Devices, Raxar, and Elevate.

real estate 210

real estate media accelerator pitching 210

This is going to be BIG.

DECEMBER 26, 2011

2004 gave us widespread blogging and Meetups, and 2008 showed how the web could be a community organizing and fundraising tool. (PS.there are various companies in this article I have or have had business involvements with. Reader beware.). Open Government. Election years tend to be good for technology diffusion.

innovation 310

innovation technology peer-to-peer communities 310

Tomasz Tunguz

MAY 2, 2022

In 2008, tightfistedness dominated the market. Today, a story is sufficient to raise a 2008-sized Series B. Given how much investors prefer faster growth rates and the massive surge in venture fund size, I don’t expect the ramen and ping-pong days of 2008 to return anytime soon. In my notebook, I sketched this 2x2.

capital 143

capital real estate enablement development 143

Both Sides of the Table

JULY 7, 2015

This is the problem that first-time entrepreneurs who have never been through a downturn (we haven’t had one since 2008) couldn’t have the muscle memory for and thus it seems “all good” right now. It won’t be. I’ve seen the movie on the other side of economic shifts.

startup 323

startup advice pitching VC 323

Entrepreneurs' Organization

OCTOBER 4, 2023

My first company, a mortgage bank, succumbed to the 2008 mortgage crisis. On a personal note, I’ve been there. As a Latin American businessman who ventured into the US market, I understand both sides. While external factors played a role, I needed more control and the resources to navigate the crisis effectively.

leadership 38

leadership culture economic growth education 38

A VC: Musings of a VC in NYC

JANUARY 1, 2024

Satoshi gave us the playbook to build a decentralized internet stack back in 2008 and I feel quite confident that we will have massive mainstream applications running on this decentralized stack well before 2028. AI developed for over forty years before its coming out party. I think it will take web3 less than half that time.

energy 236

energy venture capital innovation capital 236

Both Sides of the Table

MARCH 3, 2012

I had been looking around at several deals in late 2008 as the markets were tanking. I had this ethical dilemma pop up on one of the first deals I even did as a VC. I had gotten close on a couple of deals but nothing rose to the level of “must do.”

VC 356

VC financing finance investment 356

American Entrepreneurship

MARCH 12, 2025

Risk-Taking: He reinvested his entire PayPal earnings (~$180M) into Tesla and SpaceX, nearly going bankrupt in 2008. Resilience: SpaceX had multiple rocket failures before successfully launching into orbit in 2008. Problem-Solving: He tackles big problems (e.g., Lesson: Think big, take calculated risks, and persist through setbacks.

strategy 60

strategy startup creativity mentorship 60

Both Sides of the Table

JULY 24, 2012

When I couldn’t talk David into doing early-stage deals back in 2008/09, I hooked up with the guy who seemed to be working with the largest number of high-quality LA startups I had encountered – Dave Young – and started working with him and Nicholas Hobbs of DLA Piper. There’s more!

VC 299

VC communities investment investing 299

Both Sides of the Table

JUNE 27, 2021

They sold 2 years later for $16 million In the financial crisis of 2008 we had a company that had jointly hired lawyers to consider a bankruptcy and also pursued (and achieved!) the sale of the company for $1 billion. It was ~30 days from bankruptcy.

sustainability 294

sustainability board construction strategy 294

StartupNation

DECEMBER 8, 2020

Induced by a pandemic and unprecedented state responses, it is even worse than the last international period of economic decline witnessed in 2008. During the period of economic turbulence in 2008, I formed my technology consultancy firm, ROCK. For most, 2008 was a time to avoid risk.

culture 124

culture frameworks development strategy 124

Both Sides of the Table

FEBRUARY 6, 2016

Just look at our rebound from the financial crisis of 2008 as something that I feel proud of as an American. But in my core I believe that the self-healing nature of our internal struggles and competition produces a system that is more resilient and self healing. Worst system. Except for everything else.

education 189

education venture capital investment investing 189

Dream It

APRIL 8, 2020

Having been at the forefront of the dot-com boom, 9/11, and the financial crisis of 2008, Jason knows what it takes to survive this downturn. Jason sat down with Steve Barsh , Managing Partner of Dreamit, to give founders relevant downturn strategies. In fact, Jason started investing during the financial crisis.

founder 195

founder economic environments sustainability pitching 195

Angel Capital Association

MARCH 13, 2023

We commend the VC’s and angels that have rallied around their entrepreneurs to repurpose lessons learned from the 2008/2009 recession. history, behind only the 2008 failure of Washington Mutual with roughly $300 billion in total assets. and its failure is the second largest U.S.

startup ecosystem 96

startup ecosystem consulting communities venture capital 96

Both Sides of the Table

FEBRUARY 14, 2016

That was written in September 2008. In September 2008 this was the bankruptcy of Lehman Brothers and the rippling effect was massive. For every bear there’s somebody else thinking they have an opportunity. That’s the beauty of markets and of capitalism. Remember the RIP Good Times by Sequoia ?

startup 285

startup VC entrepreneurs investment 285

TechCrunch

JULY 23, 2021

During the 2008 economic downturn, Almond’s family lost their home. The company raised $50 million Series C funding led by NewView Capital, with participation from SoftBank’s SB Opportunity Fund and King River Capital. This brings the company’s total funding to $85 million, Paystand co-founder and CEO Jeremy Almond told TechCrunch.

finance 144

finance financing networking capital 144