Both Sides of the Table

MARCH 6, 2010

One of the questions I’m most often asked is, “what’s it like being a VC?&# I’ve been a VC for nearly 3 years now. Since I answer this all the time anyway I thought it might make an interesting blog post. But let’s face it, as a VC you spend time with whichever companies you want.

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Both Sides of the Table

OCTOBER 1, 2009

In the first post in this three part series I described why I believe the VC market froze between September 2008 – April 2009. I’m not a doomsday guy, but just believe that we won’t see a V shaped recovery, which could make VC funding more difficult for tech start-ups (don’t shoot the messenger!).

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Both Sides of the Table

FEBRUARY 23, 2015

I wrote this conundrum and the need to take charge of how the market define your skills in my much-read blog post on “ personal branding.” But I also have advice for the 15% that really do want to be a startup CEO. I often tell people in this scenario to focus on a VC “fixer upper.”

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This is going to be BIG.

NOVEMBER 1, 2016

This blog post is not about debating if "enough" diverse founders get funding--whatever that might mean. So if you're a super early stage with just a prototype, you might not think that a VC fund is the right fit for you--so you wind up at an angel group. VCs don't go later and angels don't go earlier. Venture investing is hard.

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Both Sides of the Table

MARCH 8, 2010

I guess let’s file this under sales & marketing advice. I recently wrote a piece for Mashable on how to create a company blog. Since it’s already written (and since I promised not to republish on my blog other than a summary) if you’re interested please have a read over there. What should you blog about?

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This is going to be BIG.

DECEMBER 5, 2012

Most conversations don't end in funding or even a follow up meeting, so your aim should be to get specific, helpful advice that moves you forward. Are you blogging really insightful takes on your industry? 7) When being introduced to a VC, you follow up first, not them. Ask me those, or did you just want me to toss up a big "9.5"

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Both Sides of the Table

AUGUST 25, 2009

This is part of my blog series “ Pitching a VC.&#. I’ve sat through a lot of VC pitches and having been CEO of an enterprise software firm for many years I’ve also sat through many customer meetings with sales teams. The following are some tips for the debate style VC meeting.

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Both Sides of the Table

DECEMBER 14, 2010

They had received a term sheet from a VC and were wondering whether to work with this firm. You’re tied at the hip to your VC. So my first advice is not to rush in the fund raising process. Get to know VCs over a long period of time so that when you’re ready to get engaged you feel you know their character.

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Both Sides of the Table

MAY 15, 2010

It’s always fun chatting with Jason because he’s knowledgeable about the market, quick on topics and pushes me to talk more about VC / entrepreneur issues. The following was available: “I kept hearing about startups that raised VC funding, but which hadn’t filed Form Ds (nor issued a press release).

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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).

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Both Sides of the Table

MAY 4, 2013

As a VC you want to feel like you have “proprietary sources” of deal flow. I eventually stumbled on to the best source of high-quality deal flow imaginable – blogging. ” I love businesses that don’t lend themselves well to VC Panels at conferences or Demo Days. Advice to VCs Startup Advice'

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Both Sides of the Table

JUNE 3, 2010

This was really a fun week at TWiVC because we decided to have an entrepreneur come and talk about raising capital rather than having a VC come on. In particular I tried to do most of the “entrepreneur advice on VC” up front so that if you don’t want to watch our views on the deals you don’t have to. They sponsor TWiVC.

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VC founder advice ventures 214

Both Sides of the Table

MAY 13, 2018

This is part of a series of advice for founders who need to raise money from venture capitalists. The most important advice I could give you before you set out in fund raising mode is to understand that fund-raising a sales & marketing process and needs to be managed. Same with VC. If in high school you got a 3.6

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Both Sides of the Table

JUNE 12, 2013

But less as a complaint and more as advice to younger networkers, the more you invest in relationships the more you will get when you need. Brunson’s short and to-the-point blog post, “ It’s Called Networking, Not Using.” It’s why I wrote the blog post on 50 Coffee Meetings. ” Be authentic.

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advice VC networking entrepreneurs 407

Both Sides of the Table

MAY 6, 2018

As a VC with scores of startups in our portfolio we have ringside seats to many, many fund raising processes plus I had to raise money across about 5 different rounds of capital as an entrepreneur so I’ve developed some thought on the process that I hope can be helpful to some of you before you start. Remind me why I love you?

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advice VC entrepreneurs SaaS 236

Both Sides of the Table

JULY 22, 2010

I just want to figure out what a fair valuation is.&# I figured all the VC’s talked so we should. How VC’s Calculate Valuation : We walked through a standard deal where you raise $1 million at a $3 million pre-money valuation leading to a $4 million post money valuation. The VC assumes you’ll have an option pool.

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founder VC venture capital entrepreneurs 405

This is going to be BIG.

APRIL 3, 2012

Instead of just e-mailing people and dealing with them directly, as we do in person, we're a blog post away from a flamewar. I think Fred was trying to offer some friendly advice to young investors that you're going to "take lumps" and that it's worth learning from those who are more experienced.

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VC board venture capital ventures 274

Both Sides of the Table

MAY 11, 2010

I haven’t written a blog post in a week. And for the last few evenings I decided to get through email rather than blog. I’ve written about the topic before when I wrote the post “ I emailed a VC but never heard back.&# As in, what do you do now that you’ve written them. Blog comments.

advice 265

advice VC entrepreneurs creativity 265

Both Sides of the Table

NOVEMBER 11, 2013

You can watch the video above for a very brief overview of why we rebranded and where we see our place in the VC ecosystem along with what has changed in our industry. Relaunching our brand is part of our larger initiative to build a VC firm of the future. When he starts his blog I’ll let you know. But I miss blogging.

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ventures VC strategy advice 324

Both Sides of the Table

DECEMBER 14, 2009

I wanted to also post the series here to have it as a resource on my blog for future entrepreneurs who stop by. One of the questions I’m most often asked as a VC is what I’m looking for in an investment. I once had a debate with a prominent VC on a panel. How to build relationships with a VC. Yeah, right.

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entrepreneurs peer-to-peer advice VC 338

Both Sides of the Table

FEBRUARY 9, 2014

I only say that because after years as a VC I can always tell when my peer group invested in something because “it seemed like it would make money” versus when they invested out of passion. On reflection of the role that I want to play as a VC it is clearly in the camp of passion. I’m a VC. Startup Advice'

peer-to-peer 373

peer-to-peer VC pitching entrepreneurs 373

Both Sides of the Table

MAY 27, 2013

By spending more time educating your board on your business you get more valuable advice from them. Your goal should be to turn your VCs into extended members of your team to get real value from them. So what are Rob’s secret hacks that he didn’t spill in his blog post? . Startup Advice' Rob does it.

board 365

board VC advice pitching 365

Both Sides of the Table

JUNE 8, 2010

I’m going to save that for a future blog post. And awesome to get to spend time with Ian Sigalow “comparing notes” (VC speak ). If you can get 30 CEO’s sitting on the edge of their seats about about 8 VC partners to not use their Blackberry’s for 90 minutes you’re really achieved something.

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peer-to-peer advice VC board 279

Both Sides of the Table

MARCH 14, 2013

The major battle for press is a battle for “mindshare” and it’s exactly the reason I blog. I am a VC. We provide strategic advice to digital media companies in a manner that reflects how corporate development is actually done. I hand out money. How differentiated is that?

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mix-use advice VC technology 389

Both Sides of the Table

SEPTEMBER 18, 2014

The frantic pace of technology cycles, the amount of tech news, the blogs, the conferences, the demo days, the announcements, the fundings, the IPOs. It got me thinking about the advice that I often give to new VCs. VC Industry' It’s exhausting. Perhaps unsustainable. Lines, Not Dots. Attitude over Aptitude.

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peer-to-peer pitching VC accelerator 317

Both Sides of the Table

JULY 15, 2010

We started this week’s show with a Q&A session where I answered viewer questions about fund raising and the VC industry. If you enjoy this blog I think you’ll enjoy watching the first 14 minutes of this video (just click on the image of me below). What advice do you have for people who want to get into venture capital?

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VC ventures venture capital advice 210

Both Sides of the Table

JANUARY 3, 2016

In the VC insider baseball world a discussion has gone on about “VC platforms” over the past 5 or so years. While firms define platforms differently, let’s just say they are the services that a VC offers outside of investment capital and partner time on boards or providing intros.

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VC peer-to-peer mix-use leadership 198

Both Sides of the Table

JUNE 27, 2013

If you’ve been following the press about VC funds you’ll know this is no small feat. VC has operated as an “old boys club”, with access to capital often requiring entrance through an elite university engineering department in one of two cities. Startup Advice' That seems pretty superficial!”.

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ventures venture capital advice VC 343

Both Sides of the Table

OCTOBER 3, 2011

On my blog I’ve been hesitant to take the topic head on. But last week I noticed a blog post by a woman, Tara Tiger Brown, that asked the question, “ Why Aren’t More Women Commenting on VC Blog Posts? In it she observes that only 3% of the comments on this blog are from women. Please watch this.

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entrepreneurs entrepreneurship VC pitching 341

Both Sides of the Table

MARCH 8, 2018

If you’re an entrepreneur who would like to see this clause in more startups please ask your VC to include it in future term sheets and link to it from their home page. “We I have seen in your 5 years with us countless hours dedicated to mentorship and advice to younger founders of color and showing them a roadmap for success.

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VC leadership mentorship entrepreneurs 284

Both Sides of the Table

JANUARY 16, 2013

I became aware of Sam several years ago as I started noticing his name repeated in the comments section of my blog. He pinged me that he was thinking about joining a startup based in LA with the CEO in NYC and would I be willing to meet him and give him advice on this process. So I had a sense that I knew who he was.

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pitching advice VC entrepreneurs 372

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. People who can invest with the firms money at arms length, bounties for sourcing a startup, small investments in other VCs that are upstream from your firm.

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startup VC strategy leadership 97

This is going to be BIG.

MAY 29, 2012

Being a good angel or VC has a lot to do with pattern matching. If you've never blogged before, you might not get what I mean, but it's akin to how our view of the world changed the moment we all started carrying around cameras in our pockets. Otherwise, all of your advice sounds like your best advice, until you tell someone else.

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peer-to-peer angel investing advice entrepreneurs 333

Entrepreneurs' Organization

SEPTEMBER 8, 2023

As female entrepreneurs, we are independent-minded and innovative, and this advice is critical for securing our future and the future of our families. She provided me with so much advice on business strategy, business channels and HR. and more articles from the EO blog.

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founder advice entrepreneurship entrepreneurs 262

Both Sides of the Table

NOVEMBER 25, 2010

This is an updated post from my ongoing series on Startup Advice that I learned from founding two companies. . On Losing in VC. I know I won’t win every deal I want to in VC. It’s one of my favorite blog posts. We assumed they would take our advice and upgrade. I HATE LOSING. I hate it.

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consulting advice collaboration VC 328

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 was back when VCs weren’t so quick to respond to emails. I was thinking about all of this as I looked at the logs from my WordPress blog this evening. I started blogging 2 years ago.

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advice VC finance financing 391

Both Sides of the Table

AUGUST 17, 2009

This is part of my ongoing series “ Pitching a VC “ There’s a great meme developing this morning on the need to simplify funding terms and documents. That prompted Fred Wilson’s blog post appealing to the industry to make these simplified term sheets standard. I have this mentality, too.

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