Both Sides of the Table

JANUARY 18, 2011

I always try hard to make this blog a place where you can learn lessons rather than an advertisement for portfolio companies. I learned that he was originally with William Morris as a junior talent rep but wanted to be more in the business of helping digital startups. Pose is no different. He wanted to be an entrepreneur.

investing 303

investing investment VC media 303

Both Sides of the Table

NOVEMBER 4, 2010

It should affect how you think if you are an incumbent but also if you’re a startup. So the startups tend to focus on totally new customers. Often the startups are actually serving a slightly different kind of customer or a slightly different market need. It is not a beach novel to be sure.

incumbents 376

incumbents disruption frameworks innovation 376

Both Sides of the Table

AUGUST 19, 2010

The researchers taped 29 hours of people working in a typical office, and found that they were interrupted on average four times each hour. Here's the kicker - 40% of the time, the person did not resume the task they were working on before the interruption. Sounds like a day at most offices.

advice 301

advice consulting entrepreneurs investing 301

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. . I don’t break tennis rackets, cry foul, fall over like an Italian soccer player or work the referees. I HATE LOSING. I hate it. I really, really, really hate it. It chaps my hide. It rips at my core. I move on.

consulting 333

consulting advice collaboration VC 333

Both Sides of the Table

JUNE 8, 2010

I’m going to save that for a future blog post. Get your product/market fit working before you ramp up your costs (or raise too much money). With all the external presenters, the ones I enjoyed the most were Dan Senor who wrote the book Startup Nation (an examination of the Israeli technology scene).

peer-to-peer 279

peer-to-peer advice VC board 279

Both Sides of the Table

MAY 11, 2010

I haven’t written a blog post in a week. I travelled for a couple of days for work and decided to get some sleep on those days rather than staying up into the wee hours as I often do when I travel. And for the last few evenings I decided to get through email rather than blog. Actually, mostly hate. Email is a chore.

advice 265

advice VC entrepreneurs creativity 265

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. . I don’t break tennis rackets, cry foul, fall over like an Italian soccer player or work the referees. I HATE LOSING. I hate it. I really, really, really hate it. It chaps my hide. It rips at my core. I move on.

consulting 328

consulting advice collaboration VC 328

Both Sides of the Table

MARCH 6, 2010

Since I answer this all the time anyway I thought it might make an interesting blog post. When I was running startups I felt like a horse with blinders on because I was super focused on the content management market and ignored many other markets. I work hard, don’t get me wrong. That’s true.

VC 312

VC consulting entrepreneurs creativity 312

Both Sides of the Table

JANUARY 21, 2010

I recently read a post over on VentureHacks titled, “ Top Ten Reasons Entrepreneurs Hate Lawyers &# written by Scott Walker (who blogs on legal issues for entrepreneurs ). This all got me thinking about a post on how to best work with lawyers. This all got me thinking about a post on how to best work with lawyers.

startup 318

startup advice entrepreneurs VC 318

Both Sides of the Table

JULY 22, 2010

Back in 1999 when I first raised venture capital I had zero knowledge of what a fair term sheet looked like or how to value my company. Due to competitive markets we ended up with a pretty good term sheet until we needed to raise money in April 2001 and then we got completely screwed. Those were the dog days of entrepreneurship.

founder 405

founder VC venture capital entrepreneurs 405

This is going to be BIG.

MARCH 1, 2010

I grew up here, went to school here, and have worked hard over the last 5+ years to help build up the NYC innovation community. And sure, there’s a little bit of bull in a china shop in me—but if I didn’t have that, I wouldn’t work nearly as hard, and frankly, I wouldn’t be me. You know what—it’s supposed to work like that!

startup 286

startup media ecology VC 286

Both Sides of the Table

APRIL 5, 2010

I commented briefly on his blog and made a mental note to write a blog post. In 2005 he was graduated and took a job in South Carolina working for technology company while he started his own web design company on the side. He started another company on the side while he was working during the day at a technology company.

education 282

education creativity innovation entrepreneurs 282

Both Sides of the Table

FEBRUARY 27, 2010

Fred Wilson said as much on his blog also. That is true of all my blog posts. It is what I love the most about debates and one of the things I love most about blogging. Let’s talk about kids for a moment. I grew up believing that human behavior was 20% nature, 80% nurture. I have first-hand observational data.

entrepreneurship 289

entrepreneurship entrepreneurs advice VC 289

Both Sides of the Table

JULY 25, 2010

I recently read a book I’d highly recommend to every reader of this blog called “ Yes, 50 Scientifically Proven Ways to be Persuasive &# by Robert B. Cialdini who is also author of a very well received book called “ Influence &# (which I plan to read). You should, too. (no, no, I don’t take affiliate commissions!).

strategy 293

strategy venture capital SaaS investing 293

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. I’ve watched people who went to the top schools, got the best grades and worked for all the right companies flame out. If you’re already running a startup you know all this. Excite, Ask Jeeves and Lycos?

entrepreneurs 338

entrepreneurs peer-to-peer advice VC 338

Both Sides of the Table

APRIL 21, 2010

Finally, a lot of people asking me about typos on my blog. In addition to the P2P deals covered below, on the show we also talked about some of my favorite financing startups ( Wonga in the UK run by Errol Damelin , who is a superstar) and Affordit.com run by serial (and I mean serial!) Really!). Peer-to-peer lending is back!

venture capital 265

venture capital peer-to-peer capital ventures 265

Both Sides of the Table

JUNE 3, 2010

Paul Graham and the folks over at YCombinator have done much to reenergize early-stage entrepreneurship and encourage the creation of many new and innovative startups including DropBox, Posterous, Loopt, Justin.TV, Scribd and many others. They also gave us Hacker News , which for me was a welcome addition for discovering tech stories.

entrepreneurship 258

entrepreneurship culture innovation startup 258

Both Sides of the Table

OCTOBER 1, 2009

That’s around 1 out of 7 working-age Americans. To understand this in great detail see this very important blog post by Henry Blodget on the unemployment rate in the US and its impact on the recovery. It is also a result of pent-up demand. In the following post I argue that this increased pace may be temporary. See point 2 below.

VC 269

VC startup advice innovation 269

Both Sides of the Table

OCTOBER 25, 2009

This is part of my ongoing series Startup Advice. Keeping a blog has been great because so many entrepreneurs have written me with questions about their companies and I’ve gotten to know many of you personally through the process. I write this post as a warning to pick your VC’s carefully. I guarantee this is a bad VC.

VC 297

VC board consulting advice 297

Both Sides of the Table

DECEMBER 19, 2009

Some readers of this blog also pointed out that “pivoting&# can be disruptive on the employees of an organization. And we know that being stubbornly tenacious without the “street smarts&# to know when market conditions are changing and then “pivoting&# when they are changing is a recipe for failure.

entrepreneurs 288

entrepreneurs advice leadership angel investing 288

Both Sides of the Table

NOVEMBER 29, 2010

Justyn Howard, founder of Sprout Social has a blog post that he’s written about his experiences of migrating from scrappy tools to more efficient ones (i.e. It’s a great topic, his post is well written and given that he’s going through it right now in his startup it’s worth reading his point of view on the topic.

culture 333

culture construction startup advice 333

Both Sides of the Table

JUNE 28, 2010

One of the most difficult things to do as a first time entrepreneur is to get to know the investors you might be working with if you accept money. I apologize for the audio quality – we did this in a rush because we found a last minute studio and recorded in San Francisco. I had an hour to interview Mike Hirshland of Polaris Ventures.

VC 230

VC ventures venture capital capital 230

This is going to be BIG.

MARCH 10, 2010

Content recommendation for years has been a startup graveyard. In the case of Techmeme, half the job is done when you curate the list of which tech blogs you should be paying attention to. And people want that—it’s why Mr. Tweet went viral and it’s what the team over at LiveIntent (FRC portfolio company) is working on.

venture capital 267

venture capital entrepreneurship networking capital 267

Both Sides of the Table

JANUARY 15, 2010

He wrote an excellent blog post on this topic. Local angel investors totaled 18 people including Matt Coffin , Brett Brewer , Kamran Pourzanjani , Jarl Mohn and many others that young entrepreneurs would be blessed to work with. As a former entrepreneur, I’m a big supporter of Jason’s goals.

advice 254

advice angel investing entrepreneurs pitching 254

Both Sides of the Table

NOVEMBER 28, 2010

Recently I wrote a blog post about how I hated losing, but I embrace it as a way to learn, improve and increase my win rates. One of the things I learned from my “post-game analysis&# is that you’re most vulnerable right after you’ve won the deal. I won, that is, until I lost. What would Leo the Lip think of me?

consulting 309

consulting advice VC support 309

Both Sides of the Table

DECEMBER 1, 2009

This is part of my ongoing series on Startup Advice. If you’ve read my blog for a while you’ll know that I’m a fan of starting businesses in a non-traditional way. I recommend that you start a company by yourself and own 100% of it. I recommend that you start a company by yourself and own 100% of it.

startup 289

startup advice entrepreneurs creativity 289

Both Sides of the Table

AUGUST 10, 2010

Ask me something very narrow that I can answer without typing a whole blog post length response. An entrepreneur recently sent me an @ reply message on Twitter asking for some help with a decision coming up in his business. I get these frequently via Twitter, Facebook or email. I don’t mind. I can’t always get to them.

advice 332

advice entrepreneurs investment investing 332

Both Sides of the Table

JANUARY 26, 2010

They can tell you the square foot costs of their property, they can tell you how much they spend on Amazon Web Services every month, they can tell you the 12 features that you’re working on for your next release. This is part of my series on what makes an entrepreneur successful. Can’t go a mile deep on competition?

entrepreneurs 286

entrepreneurs advice pitching VC 286

Both Sides of the Table

MAY 15, 2010

Nevertheless, if you share too much in your funding process or meet too many VCs expect a certain amount of your ideas to spread around the startup community. 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). We spoke briefly about why.

VC 285

VC financing finance capital 285

Both Sides of the Table

MARCH 5, 2010

This showed me that the system worked well. They’ve done some clever things to improve the trust factor like doing background checks and other verification techniques to improve the trust people have in working with service providers. Then let’s hope both startups can build national practices. Watch this space.

education 254

education pitching VC media 254

Both Sides of the Table

AUGUST 18, 2010

But if I asked you instead whether you want to work on things that are urgent or not urgent it requires more consideration. I know that would be surprising to many readers since keeping a blog somehow convinces people that I’m a time management or productivity ninja. When I first discovered the concept I found it enlightening.

mentorship 374

mentorship creativity energy entrepreneurs 374

Both Sides of the Table

SEPTEMBER 16, 2010

I know some people think the whole market has been disrupted and startups and funding work differently these days. How’d that work out? Deep pockets – In the previous posts I’ve compared tech startup investing with poker taking analogies of The Big Short & Delivering Happiness. I doubt it.

angel investing 283

angel investing investing investment disruption 283

Both Sides of the Table

AUGUST 18, 2009

This is part of my ongoing series, “ Startup Lessons.&#. Yesterday I wrote a blog post ( here ) in which I urged people to not have too many founders. Real world story – a friend of mine used to work at Google. Best case scenario in my mind is just 1, but at most I recommend 2. Should he/she keep 50%?

founder 251

founder advice entrepreneurs VC 251

This is going to be BIG.

SEPTEMBER 1, 2010

Unfortunately, that’s really not the case for most startups. In all four deals that I’ve worked on, we were the first ones to the table. In all four deals that I’ve worked on, we were the first ones to the table. Mark Suster , Seth Levine , Fred Wilson , and Chris Dixon have all weighed in and there’s more on RWW.

entrepreneurs 262

entrepreneurs venture capital SaaS support 262

Both Sides of the Table

SEPTEMBER 25, 2010

When I first read Paul Graham’s blog post on “High Resolution&# Financing I read it as a treatise arguing that convertible notes are better than equity. Most early-stage entrepreneurs who have worked with me (either as an angel or as a seed VC) know that I don’t rely at all on the social proof of other investors.

financing 286

financing finance advice VC 286

This is going to be BIG.

MAY 27, 2010

No startup on the face of the earth has ever gotten so much free PR in the history of entrepreneurship. Momentum at the right time paves the way for startup success. Building a successful company is super hard. Take Twitter, for example. They got into a Twitter conversation that lasted a full six minutes.

VC 186

VC venture capital media board 186

Both Sides of the Table

AUGUST 30, 2010

Seth Levine of Foundry Group addresses this important topic this morning on his blog with a post, “ Has Convertible Debt Won ?&# Seth was basing this on a Tweet by Paul Graham that said&#. “Convertible notes have won. Every investment so far in this YC batch (and there have been a lot) has been done on a convertible note.&#.

finance 319

finance financing entrepreneurs advice 319