Both Sides of the Table

JUNE 5, 2015

Over the years I’ve written extensively about the downsides of convertible notes for startups such as here , here and here. ” Today I want to talk about how a VC thinks about equity pricing on your round and particularly if you’re coming off of a convertible note. ” That is a problem for the founder and the VC.

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This is going to be BIG.

JUNE 16, 2014

How long does it take from first meeting a VC to getting cash in the bank? Similarly, I got introduced to Chantel Waterbury from chloe + isabel by Bo Yaghmie from Cooley, who was my lawyer when I had a startup--so I had to trace back when I first got introduced to Bo by Fred Wilson. That''s an interesting question.

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Both Sides of the Table

MAY 30, 2018

VC firms see thousands of deals and have a refined sense of how the market is valuing deals because they get price signals across all of these deals. I thought I’d write a post about how to talk about valuation at a startup and give you some sense of what might be on the mind of the person considering funding you.

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This is going to be BIG.

JANUARY 22, 2018

This will be the post where I dangerously attempt to walk the minefield of a white male VC opining on the topic. Besides, how effective of a filter is it that someone can get coffee with a non-VC and convince them that you'd want to see the deal? That pitch has never excited any VC in the history of VC funding.

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A VC: Musings of a VC in NYC

OCTOBER 25, 2021

When you look at the recent Q3 numbers on seed and early-stage VC fundraising, you might think we are in the late stages of a VC bubble: The words I would use to describe the current environment in early-stage VC are “fast and furious.” It has never been easier to start a company, build a team, and build a product.

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Both Sides of the Table

AUGUST 30, 2014

Many startups now go through accelerators and have mentors passing through each day with advice – usually it’s conflicting. There are bootcamps, startup classes, video interviews – the sources are now endless. Improving startup productivity ? Startup psychology / confidence ? What is a founder to do?

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Both Sides of the Table

MAY 13, 2018

If you truly believe that you, your company and your products are exceptional and your company will be valuable then you’re actually doing them a FAVOR by helping them invest in your startup. The typical VC process is as follows: They say there are three rules in property: Location, location, location. Same with VC.

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Both Sides of the Table

NOVEMBER 29, 2014

In fact, my salary never caught up with my pre startup salary across 2 companies and 8 years. I will speak with people earning good money at a larger company or even well-financed startup who are mulling over the choice of whether or not to quit. That’s less than most startup CEOs who have raised a few rounds of VC are paid.

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This is going to be BIG.

SEPTEMBER 20, 2021

That prediction obviously turned out pretty wrong, but it did drum up a whole lot of chatter about the right ingredients for building a startup community—about New York vs Boston on the East Coast and whether cities like Austin and Seattle would ever break through. Startup founders always need help. New Yorkers help each other out.

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This is going to be BIG.

MAY 11, 2015

In case you're curious what the deal funnel means for my time, I did that, too: Seeing an opportunity could mean an e-mail, a calendar request, a pitch at a demo day, a news item, a LinkedIn position change--really anything that makes me conscious that a new startup might exist.

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This is going to be BIG.

MARCH 21, 2025

I cant tell you how many times I got announced as a successful VC when I was introduced on a panel or sat across the room from a potential limited partner telling them I was. This is what I know it feels like for a lot of founders and investors alikefloating in the rarified air of extremely successful people defined by their outcomes.

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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. I had just left Salesforce.com where I was VP, Products, after they had acquired my second startup. VC is a long-term business Some businesses are overnight successes but few of them really move immediately up and to the right. Over the past 2.5

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Both Sides of the Table

JUNE 17, 2017

There are certain topics that even some of the smartest people I talk with who aren’t startup oriented can’t fully grok. It’s common cocktail party chatter to hear people confidently pronounce that some well known startup is sure to blow up because, “How could they succeed when they’re not even profitable!” What did they actually do?

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Both Sides of the Table

JUNE 13, 2018

As a VC and former entrepreneur let me offer you some advice. Remember that the goal of an email to a VC or an introduction from a trusted mutual connection is simply to get you the meeting. Remember that the goal of an email to a VC or an introduction from a trusted mutual connection is simply to get you the meeting.

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Both Sides of the Table

MAY 4, 2015

Try to imagine if you *didn’t* already know Amazon and the company walking into VC meetings telling people they were going to disrupt the selling of all goods starting with books but then extending into electronics, apparel, toys and so forth. Today’s asset – real estate – is tomorrow’s albatross. ” Ha.

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This is going to be BIG.

JUNE 22, 2020

If you’re going to try to pitch metrics and momentum as the main feature of your pitch—make sure they’re as great relative to other startups as you think they are. To a VC, $50,000 a pre-sale isn’t really that much. The key is understanding that VCs want to see what could happen, and how not what will most likely happen.

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A VC: Musings of a VC in NYC

OCTOBER 15, 2020

I wrote yesterday , about the quarterly numbers for VC investing activity: If this was a student coming home with a report card, it would be straight As. I have not seen the data to back that up but if it is true, that is also a failing grade for the VC sector. It feels like positive change is happening.

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Both Sides of the Table

SEPTEMBER 10, 2021

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. By definition?—?I’m The legends of Silicon Valley?

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This is going to be BIG.

FEBRUARY 27, 2023

That’s what every VC is telling their portfolio companies these days. If you don’t realize that, just imagine you’re a VC fund with some dry powder in the second half of 2023. The one question every VC needs to be able to answer on the way to getting to a “yes” is, “Can this return a big chunk of my fund one day?”

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Dream It

FEBRUARY 5, 2021

We did a previous dose on 5 things investors wish startups knew. Managing Partner, Steve Barsh , sat down to give us 5 MORE things investors wish startups knew. Keep reading for some more of the most common mistakes startups make when pitching and for Steve’s tips on how to fix them. Go here if you missed it.

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Both Sides of the Table

NOVEMBER 13, 2014

Investment experience (5 years a VC at Battery Ventures). Startup CEO experience (Founded P.S. XO along with my good friend Soleil Moon Frye. But there are tons of great startup folks so you need a narrower filter. Upfront Ventures VC Industry' billion IPO), Envestnet (Chicago, $1.25

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A VC: Musings of a VC in NYC

OCTOBER 14, 2020

The NVCA and Pitch Book are out with their Q3 report on the VC industry and what they report is that the VC industry continues to be very active throughout the pandemic. The startup economy is alive and well during the pandemic. Deal counts and deal values are stable to up over last year. Valuations continue to rise.

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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. Some force that pulls exceptional startups to you, directly or via intermediaries, in a privileged and sustainable fashion. What’s my needle magnet definition?

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This is going to be BIG.

APRIL 6, 2015

Turns out that not only is he real, but he''s one of the most genuine, thoughtful, and egoless people I''ve met in the startup world--a real breath of fresh air. You''ve been in VC long enough to see lots of different funds, partners and deals. You get a lot of choice as a VC as to who you want to spend your time with.

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Both Sides of the Table

AUGUST 20, 2015

VC funding. We love capital efficiency until we love land grabs until we abhor over funding until we get huge payouts and ring the bell for more funding until we attract every non-VC on the planet to invest in startups until it crashes and we start the cycle all over again none the wiser. You are building a one-option startup.

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Dream It

APRIL 24, 2019

Over the past week, Zillow announced the rollout of their 3D Home tool, which lets real estate agents show immersive VC views of homes for sale. The startup partners with local real estate photography and video firms to get its product into the hands of users. The company, which raised a $1.3

real estate 288

real estate construction startup enablement 288

Both Sides of the Table

FEBRUARY 12, 2019

Round sizes of > $100 million or more now account for 47% of all VC dollars (62% if you count rounds > $50 million) This has made venture capital significantly more valuable for VCs and LPs who invest in the best companies As part of our study we noticed a trend many have spotted but few have explained?

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Dream It

APRIL 7, 2020

Friday, April 3 was supposed to be the orderly launch of the CARES Act Paycheck Protection Program (PPP) providing $349B of urgently needed funding to struggling startups and small businesses. What are the immediate do’s and don’ts for startups? For instance, one of our startups applied to J.P.

startup 348

startup communities VC ventures 348

Both Sides of the Table

DECEMBER 11, 2022

Something happened in the past 7 years in the startup and venture capital world that I hadn’t experienced since the late 90’s — we all began praying to the God of Valuation. How might our next phase of the journey seem brighter, even with more uncertain days for startups and capital markets? What happened? There was no money train.

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Both Sides of the Table

NOVEMBER 14, 2017

Nearly every successful tech startup I’ve observed over the past 20 years has gone through a similar growth pattern: Innovate, systematize then scale operations. Innovate In the early years of a startup there is a lot of kinetic energy of enthusiastic innovators looking to launch a product that changes how an industry works.

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MAY 24, 2021

But markets have changed and I think investors, founders and experienced executives who want to join later-stage startups can all benefit from playing the long game. Of the first four investments I made as a VC in 2009, two have exited and two (Invoca & GumGum) still are independent and likely to produce $billion++ outcomes .

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Both Sides of the Table

OCTOBER 7, 2014

No VC will be so naive as not to see straight through it. When I first became a VC, seed rounds were typically $500k – $1.5 There weren’t a lot of seed funds in 2007 so this was often done by angels, funding consortia or sometimes early-stage funds that existed then (First Round Capital, True Ventures, SoftTech VC, etc.).

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VC advice finance financing 399

A VC: Musings of a VC in NYC

MAY 5, 2021

There has been this narrative about investing in VC funds that you have to get into the top quartile (25%) or possibly the top decile (10%) in order to generate good returns. I have heard that for as long as I have been in VC and probably have written it here a few times. As you can see, investing in VC funds can be very profitable.

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Both Sides of the Table

JULY 26, 2022

2021 saw phenomenal returns for our industry and it topped off more than a decade of unprecedented VC growth. We feel blessed to work alongside startup founders who are really rising to the challenge of the more difficult funding environment. Thank you to everybody in the community who has supported us all these years.

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Both Sides of the Table

DECEMBER 16, 2014

The speaks to the continued confidence in the venture capital markets and as I had predicted some time ago the VC markets right now are a great place to invest – especially relative to other places to put one’s money. If you want to understand how the VC industry is changing there is a great primer in the link.

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Dream It

APRIL 12, 2020

During our recent Dreamit Kickoff week, Bullpen Capital Founder and General Partner Paul Martino ( @ahpah ) spoke with our Spring 2020 cohort about the state of the VC ecosystem in the current economic crisis. Startups should know how VCs work. startup) per month.

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Both Sides of the Table

NOVEMBER 19, 2015

I’m often asked about the differences between being at a VC and being an entrepreneur and whether I prefer one or the other. The biggest difference I cite is that Venture Capital often feels like an “individual sport” while startups are a “team sport.” That’s what we’re trying to do at Upfront.

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