Both Sides of the Table

SEPTEMBER 14, 2010

I believe the rise in angel investing is here to stay and the professionalization of this class (aka “super angels&# or “micro VC&# ) is a good thing for the VC industry and for entrepreneurs. But I fear that for most angel investors who invest over the long haul angel investing will not be a profitable endeavor.

angel investing 306

angel investing investment investing VC 306

Both Sides of the Table

OCTOBER 17, 2009

A few years ago it became fashionable for large VC’s to do seed funding. If the large VC doesn’t agree to do your A round then you’re in a bit of trouble. But I’m no longer an entrepreneur – I’m a VC at a $200 million fund called GRP Ventures , the largest active fund in Southern California.

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VC real estate advice venture capital 283

Both Sides of the Table

SEPTEMBER 10, 2021

By definition?—?I’m I’m over-paying for every check I write into the VC ecosystem and valuations are being pushed up to absurd levels and many of these valuations and companies won’t hold in the long term. However, to be a great VC you have to hold two conflicting ideas in your head at the same time.

ventures 471

ventures VC venture capital funders 471

This is going to be BIG.

AUGUST 8, 2011

How about as a VC? He hasn't founded or built either a successful, let alone innovative company, and he hasn't raised $ to invest in those entrepreneurs. Fred has basically always been a VC, Mike was a reporter, and Jim worked in product marketing and management consulting. "Charlie is a nice guy, but his company failed.".

VC 275

VC peer-to-peer board advice 275

Both Sides of the Table

JANUARY 11, 2011

If you want a very quick primer on all the stuff nobody ever tells you about raising venture capital check out this video where Mark Jeffrey & I break it down on This Week in VC. All of this is covered in more detail on the TWiVC video above (and much of it is covered in text on this blog on the “ Raising VC &# tab).

VC 340

VC venture capital leadership pitching 340

Both Sides of the Table

SEPTEMBER 14, 2010

And we all know that Ron Conway is considered the savviest of angel investors and yet by definition not all of his investments succeed. I like to invest where I have a personally strong connection with the entrepreneur and/or a strong intuition on the market from prior experience. Who ultimately invested in FourSquare?

angel investing 288

angel investing investment investing advice 288

Both Sides of the Table

APRIL 3, 2010

Because it is a “series&# I plan to get into some of the deeper complexities of funds such as “cross over funds&# and “why VC’s hate to price their own deals&# at a later stage. First, if the VC does 15-20 of these under one partner then it is certain he can’t spend any time with these investments.

VC 265

VC venture capital entrepreneurs investing 265

Both Sides of the Table

SEPTEMBER 29, 2013

.” From the hyperbolic Jason Calacanis weighing in that “The petty VC’s did everything to deride [Naval, the co-founder of AngelList]” as though the industry was collectively s g its pants that AngelList was going to put us out of business. This is the same way VC firms, by the way. So there you have it.

VC 356

VC peer-to-peer board entrepreneurs 356

This is going to be BIG.

DECEMBER 21, 2012

Three companies most definitely makes a pattern. You're going to miss some stuff, and just because others invested doesn't make any of these companies winners quite yet, but I'm all about continuous improvement. Linden's a cool dude and being the interchange between the internet of things, our social services, etc.

VC 253

VC education entrepreneurs development 253

This is going to be BIG.

NOVEMBER 4, 2018

When you get an investment from Brooklyn Bridge Ventures—you get me. My investment thesis is shaped by the sum of my personal experience and so are my values. My goal is to make Brooklyn Bridge Ventures the most accessible VC firm not just because I think it’s good business, but because I think it’s a based on good values.

investment 266

investment investing communities founder 266

Both Sides of the Table

SEPTEMBER 22, 2012

” This is a frequent theme of mine when asked to speak to audience about the VC industry. And this is fueled by the VC culture in Silicon Valley. I was recently talking to a VC about a business I was looking at and I was asking whether he found the business interesting, too. It is VC math, like it or not.

startup 390

startup VC venture capital entrepreneurs 390

Both Sides of the Table

OCTOBER 17, 2019

I became a VC 12 years ago in 2007 when the pace of deals was much slower. As I was trying to figure out the role I wanted to play in the VC world I decided I wanted to focus on businesses that were building deeply technical products to solve problems for business users. We not only have our Series A funds that can write $500k?—?$15

VC 223

VC venture capital capital investing 223

Gust

OCTOBER 8, 2014

Marc Andreessen kicked off another great debate on Twitter last night, one that I’ve been talking about incessantly in private circles for the past 2-3 years – what actually IS the definition of a seed vs. A-round. My view: “Spending any time or energy trying to game the ‘definition’ of your round of fund raising is a total waste.

VC 136

VC advice finance financing 136

This is going to be BIG.

APRIL 29, 2011

Then I realized that it's probably not obvious what the dynamics are around how VCs tend to get introduced to companies and what works best for people, so I figured I'd blog about it. A lot of VCs ask to be introduced through someone. And these represent some of our most successful investments. Would you invest in it.

VC 292

VC pitching entrepreneurs networking 292

This is going to be BIG.

APRIL 3, 2012

Age, gender, sexual orientation, religion, etc are all topics that are deeply emotional for people--and, by definition, personal. Of course, you don't always need that experience from a VC. If you make a comment about age, it will always be taken in the context of how old you are versus how old your audience is.

VC 262

VC board venture capital ventures 262

Both Sides of the Table

FEBRUARY 22, 2011

When this first ran on TechCrunch I got the greatest comment in the world that I had to repeat here, “VC’s are like martinis: the first is good, the second one great, and the third is a headache.&# I understand the appeal of having many VC firms on your cap table. These are all dumb reason to invest – of course.

VC 314

VC advice pitching investing 314

Both Sides of the Table

JUNE 22, 2021

Whilst there are a wide range of LPs and you could have first meetings for months (and many VCs do), there is probably a much smaller number of LPs who want to invest in a fund your size, with your focus, and whose minimum or maximum check size lines up with what you’re seeking. Why Buy Me? For Upfront, it’s about Los Angeles.

investing 375

investing investment ventures pitching 375

This is going to be BIG.

APRIL 6, 2015

I''m just trying to invest in the best opportunities. I can definitely think of a few people I met with and said, "Well, that person was kind of a jerk" or they just had a bad personality--and they went on to build seemingly successful businesses. You''ve been in VC long enough to see lots of different funds, partners and deals.

VC 377

VC collaboration disruption founder 377

This is going to be BIG.

AUGUST 25, 2023

A recurring theme in a lot of my BSList posts is that, if an investor thinks they can make a boatload of money with you, they’ll go to all sorts of lengths to invest. That includes investing way earlier than they would normally, investing outside of scope, investing with their personal capital outside of the fund, etc.

founder 367

founder VC board pitching 367

Both Sides of the Table

SEPTEMBER 27, 2010

And that was evident on today’s Angel vs. VC panel. The VC industry is segmenting – I have spoken about this many times before. The VC industry has different segments in it that have different fund sizes, different investment amounts and different risk / return expectations. Answer: Not much.

disruption 308

disruption VC entrepreneurs financing 308

This is going to be BIG.

APRIL 14, 2014

Last week, there was a Business Insider article measuring the percent of female founded companies that NYC seed funds invest in. That means you actually have a *better* shot, statistically, of getting VC investment at these firms, statistically, once you actually pitch. In truth, that''s what''s actually driving my investments.

founder 392

founder pitching mix-use venture capital 392

Hunter Walk

FEBRUARY 22, 2025

Ok, back to the VC content marketing. As a result I’ve seen hundreds of VC decks, all certain they will be among the top performers. Most strategies are some combination of innovation and best practices along the classic five steps of venture investing: See, Pick, Win, Service, Exit. This post is about ‘seeing.’

startup 89

startup VC strategy leadership 89

This is going to be BIG.

SEPTEMBER 23, 2015

I was having a conversation last night with another VC who was suggesting I monetize the pro-ratas that I don't take by creating SPVs. It made me think of an investment I just made where the entrepreneur found an extremely profitable niche that he is already taking advantage of. But you could charge fees or at least carry for that.

advice 374

advice VC opportunity entrepreneurs 374

This is going to be BIG.

FEBRUARY 21, 2021

Any VC will tell you that the ones they said yes to, they mostly got there right away—and that there are very few “maybe” deals that get tipped over the fence. Here’s the way I look at the math: Let’s go over the structural bias first—the “pipeline” that happens before you ever even get near a VC. First is network bias.

advice 450

advice pitching venture capital VC 450

Both Sides of the Table

JUNE 22, 2011

I spoke about how Amazon Web Services deserves far more credit for the last 5 years of innovation than it gets credit for and how I believe they spawned the micro-VC category. I said that I felt that Micro-VCs were the most important change in our industry. It is great for entrepreneurs and great for VCs. I believe that.

real estate 309

real estate entrepreneurs financing finance 309

Both Sides of the Table

MARCH 6, 2011

When I described to people why I initially invested my calls went something like this, “He’s taken kicks to the face for nearly 2 years and is still standing. I was sick of hyperbole articles pronouncing that VCs were “scared or AngelList&# or “it was disrupting VC&# or some other BS exaggeration like that.

VC 292

VC peer-to-peer investing investment 292

Both Sides of the Table

OCTOBER 6, 2010

But in my experience as an entrepreneur and now spending my time amongst investors I can generalize that almost all VC investments in early stage technology & Internet investments come down to just four key factors. And VC’s are tough customers. I obviously don’t speak for all investors.

startup 360

startup VC advice entrepreneurs 360

Both Sides of the Table

JULY 10, 2012

I’ve been meeting with LPs (those who invest in VC funds) over the past year and discussing trends I see in the market and where I think we need to be as a firm to be near to and meet the needs of our customers. I think NY has always – by definition – been urban. These days it’s Santa Monica and Venice.

technology 313

technology incubation VC ventures 313

Both Sides of the Table

FEBRUARY 7, 2016

The interview was wide ranging and discussed everything from USVs investment thesis over the past 10 years to what some emerging themes are around blockchain and artificial intelligence. Dan asked Fred about “generational change” at USV and in the VC industry more broadly.

VC 176

VC peer-to-peer board disruption 176

Both Sides of the Table

JANUARY 18, 2014

If the deal is from out of your geography and/or out of your focus area or a deal is being referred by a well-know investor who normally co-invests with similar syndicates – at least ask yourself, “Why am I so lucky to be getting this call.” Fred Wilson said it best in his post about loss ratios in VC.

VC 337

VC consulting strategy entrepreneurs 337

Entrepreneur's Handbook

NOVEMBER 17, 2020

Since then, I’ve founded several startups, was employee #3 at a $65m VC firm in San Francisco, and realized that there is a similar phenomenon to what Robert Kiyosaki is talking about in Rich Dad, Poor Dad currently occurring in Silicon Valley. Wealth My definition of rich is having a passive income that’s greater than your burn.

founder 144

founder VC venture capital entrepreneurship 144

Both Sides of the Table

SEPTEMBER 26, 2015

One of the least understood parts of the venture capital industry and venture capital firms is how investment decisions actually get made. For anything that would be considered a normal investment for the partnership most firms try to make sure every partner has seen the deal and has a chance to weigh in.

venture capital 336

venture capital peer-to-peer capital ventures 336

This is going to be BIG.

OCTOBER 22, 2017

Remember that we're lucky to be investing in your company, because ideas as good as yours don't come around too often, and that will change your approach as you try to gather your first check. There was a time not too long ago when VC bios read "Fab investor", "Quirky investor", and "Gilt investor". No one is perfect.

VC 333

VC advice pitching opportunity 333

TechCrunch

JANUARY 25, 2023

There was a brief, beautiful moment for a few months in 2021 when it felt like robotic investments might be immune from broader market forces. Image Credits: Crunchbase A couple of top line points: 2022 was the second worst year for robotics investments over the past five years. Uncertainty doesn’t breed investing confidence.

investment 90

investment investing accelerator board 90

Both Sides of the Table

SEPTEMBER 27, 2012

Recently I wrote a post arguing to make the definition of a Startup more inclusive than that to which Silicon Valley, fueled by Venture Capital return profiles, would sometimes like to attach to the word. Think USV is only invested around Union Square in NYC? This article originally appeared on TechCrunch. Think again. Angry Birds?

communities 378

communities startup venture capital capital 378

Both Sides of the Table

JANUARY 31, 2011

I’m enjoying being a VC. I thought I’d talk a bit about the differences I’ve experienced between being an entrepreneur & a VC – you know, from “both sides of the table.&#. I’m sure everybody has their own definition of the attributes of an entrepreneur. VC meetings going well. 2 million in VC.

entrepreneurs 384

entrepreneurs startup VC real estate 384

Gust

DECEMBER 27, 2012

Understand what investors are looking for , what they usually invest in, and why. There is a vast gulf between a ‘cool product’ and an ‘investable company’ and if you don’t understand the difference, you will be doomed before you start. Now, and only now, are you prepared to start fundraising.

investment 164

investment investing pitching mix-use 164