Graeme Thickins on Tech

Reflections & analysis about innovation, technology & startups, with a focus on Minnesota, Land of 10,000 Lakes

Tag: founders

Brad Feld On When to Quit Your Day Job

(Note: This interview first appeared at — “Your Source for Local Innovation” in  Minnesota: Innovation, Startups, and Tech.)

Brad Feld, one of the most admired VCs, talking at event

Brad Feld, coauthor, “Startup Opportunities: Know When to Quit Your Day Job”

Few VCs have the success record of Brad Feld of Foundry Group in Boulder, Colorado, and even fewer as many writing credits. That includes several best-selling books. Well, now he’s uncorked another title, this time with coauthor Sean Wise, the subtitle of which addresses that vexing question most every would-be entrepreneur faces: when do I know it’s time to go all in and quit my day job?

I first met Brad in 2007, the year I began attending a tech conference he helped launch in Denver called “Defrag.” (And I reported on it every year for 10 years.) That was also the year Brad cofounded Techstars, and I was lucky enough to sit next to him at dinner and get the download on those plans. I so tried to get Minneapolis to become one of the Techstars cities, but, alas, it wasn’t to be back then. Eventually, of course, the accelerator found its way to Minnesota as our startup community strengthened, launching Techstars+Target and smaller programs at Mayo Clinic and Land O Lakes. Also, after years of encouraging Brad and his partner Seth Levine to look at investing in Minnesota, Foundry Group led a Series A in a startup they discovered called LeadPages, and they continue to watch what’s happening here.

When I got a look at Brad’s new book, and loved it, I immediately wanted to know more.

Q: Brad, were you surprised this book so quickly hit the list of top five best-selling business books on Amazon?

Yes. While I was confident that it would be popular, especially at a discounted price for a short period of time, I was overwhelmed and excited by the number of people who grabbed a copy.

Q: The original version of the book was published in 2014. Why did you and your coauthor decide to publish a second edition?

The first edition was published by FG Press, a publishing company that my partners and I at Foundry Group started. FG Press wasn’t successful so we shut it down, but we were proud of “Startup Opportunities” as a book. I had previously (and am currently) publishing with Wiley. They were enthusiastic about doing a second edition of the book. We added a few chapters, cleaned stuff up, and had Chris Sacca write a foreword.

Q: While the title of book is somewhat bland, the subtitle — “Know When to Quit Your Day Job” — is certainly not. Tell us about that came about, and why.

My coauthor Sean came up with it. He is quick with a one-liner and often talked to his students about the key to starting a new business was to identify the right opportunity. He often said that “friends don’t let friends pursue bad opportunities,” and one day the line “Know When to Quit Your Day Job” popped out.

Q: You make it very clear the book is intended primarily for first-time entrepreneurs. But it’s no secret they have a hard time getting attention from VCs. Is the book your way of trying to help the many thousands you have to say “no” to? I’m of course alluding to your famous blog post in 2009, “Saying No In Less Than 60 Seconds.”

When I look at the hundreds of companies I’ve funded (well over 500 at this point), greater than 50% of them were started by first-time entrepreneurs. However, even if I’ve invested in 300 companies started by first-time entrepreneurs, I’ve probably said no to 10,000 or more. I often get asked for feedback after telling someone no. Given that volume, there is no way to give people deep feedback. So, I thought a book around Startup Opportunities would be helpful to be able to point at.

Q: Of all the things this book tries to teach entrepreneurs — the realities of doing a startup — what’s the one thing you find is the hardest for them to understand or accept?

That the idea is useless. Ideas are cheap. Ideas flow freely. Lots of people have the same idea at the very beginning. The idea is not what matters. It’s what you do with the idea that matters.

Q: Are millennial entrepreneurs different? What would you say about their expectations? Are they coachable?

I work with entrepreneurs born between 1950 and 2000. Everyone – each entrepreneur – is different. I wouldn’t categorize them by the generation they belong to.

Q: Why are early-stage investors so focused on “the team”?

It’s really hard to be a solo entrepreneur. Having a great, effective, and well-functioning founding team makes an enormous difference. And, the greatest killer of startups is team issues.

Q: Knowing you have, in fact, invested in first-time entrepreneurs in your day, have many of those been financial winners? And will you continue to invest in first-time entrepreneurs?

Yes and yes. Many of the successful companies that I’ve been an investor in have been started by first-timers. And, if you look at my last few investments, I think each of them has at least one first-time entrepreneur on the team.

Q: You’ve written or cowritten so many great books for entrepreneurs. How do you keep it up? Do you have a writing schedule? You’re also a prolific blogger. How many hours per week do you devote to writing?

I try to blog daily, but I go through phases where I need a break because I don’t feel like my writing is fresh. I’m in one of those modes now and have taken a few weeks off from blogging and am getting ready to start again. Regarding my books, I go through phases. I’ll have very productive periods where I can write for two or so hours a day. I then have long stretches, often many months, where I don’t work on any books. My general pace right now is about a book a year, but it’s lumpy. I don’t really segment my time carefully, so I don’t really know how much I write each week. And, I spent a ridiculous amount of time writing email – does that count?

Thanks, Brad. The new book is fantastic. Congratulations to you and your coauthor, Sean Wise. We’ll continue here in Minnesota to practice the things you recommend in another of your great books, “Startup Communities.”

I’ll Be Live-Blogging the ‘Pioneer Summit’ Again Next Week

pioneersummit-logodatesI’m heading out to the Bay Area in a few days to once again cover a great tech conference called the Pioneer Summit, put on by GSV Labs in Redwood City, CA. I loved reporting on it last year — as evidenced by my extensive liveblog. (They moved it up from October to September this year.)

I’m looking forward to the program, which is jam-packed. Is this enough speakers for you? Here’s one my data geek friends would like. And hearing what this Silicon Valley legend has to say will be pretty awesome as well.

What is GSV Labs, you ask? It’s “a campus of innovation” — I like that description! A very cool place indeed. It’s focused on accelerating high-growth, high-impact verticals in the areas of EdTech, Sustainability, Big Data, and Mobility. Utilizingpioneersummit-celebrate GSV Labs’ resources, founders and entrepreneurs join a global network of ecosystem partners, including corporations, international agencies, mentors, universities, investors, thought leaders, and non-profits. From its Silicon Valley campus, GSV Labs houses about 100 startups, provides acceleration programs, and hosts events.

My connection to GSV Labs is through my colleague Mark Moe (who lives here in the Twin Cities) — he’s VP of Global Business Development. Look forward to seeing you there, Mark, and I’m sure some other Minnesotans who’ll be in attendance, as there were last year.

I guess I’d better start getting my live-blogging fingers loosened up — which means not just providing commentary, but shooting a whole lot of iPhone pics to go along with it. This will be fun!

Chris Shipley Speaks: The Real Scoop on Why the DEMO Producer Is Moving On

The DEMO conferences have a long, rich history, serving for some 19 years as "The Launchpad for Emerging Technology."  It's a brand like no other in the conference business.  And I can say that as someone who's been reporting on a wide range of technology conferences for more than a decade.  DEMO isn't so much a meeting or event as it is a spirit, a dedication, a community of people who celebrate new ideas and product innovations, and the thrill of building those into companies. (There's a lot more on the DEMO web site, and here's their About page.)

As closely as I follow all things DEMO (and I attend both their flagship U.S. events, spring and fall, every year), I was as shocked as anyone when a press release jumped out at me as I scanned my email inbox around midnight on February 18, saying DEMO was forging a long-term partnership with VentureBeat, and, after 13 years as executive producer, Chris Shipley was passing the torch to VentureBeat's Matt Marshall.


The next day, I emailed Chris and asked if she'd consent to be interviewed.  I thought the week before DEMO '09 would be a good time (in the lull as we press and bloggers anxiously await the well-guarded list of who will be presenting at the event) to delve into the background behind this startling news announcement, and get Chris' own words on why and how it came about. She was kind enough to agree. I especially wanted to cover this story because a mini-firestorm had erupted in the blogosphere of conjecture and commentary on this news, and I felt a real need to clear the air. So, she and I conducted the following email exchange over the past couple of days. (Just as background, Chris is CEO and founder of her own analyst firm, Guidewire Group, and has been throughout her entire stint as DEMO's executive producer.)

DEMO-08-closingshot375w Tech~Surf~Blog:  Chris, how hard a decision was this to make?  Have you been considering it for some time?  What made this the right time? 

Chris Shipley:  Neither I nor Guidewire Group took this step lightly.  DEMO has been a big part of my career and a key client to Guidewire Group for a long time, and it's difficult to make a big change like this.  At the same time, I've been able to accomplish many of the goals I've set for DEMO, and while there is still a long and rich future ahead of the DEMO brand, Guidewire Group poses new and bigger challenges, challenges that I find very exciting.  Is there ever a "right time" to make a big change?  I'm not sure, but I do know that Guidewire Group's focus — working with young companies as they face significant points of transition — couldn't be more needed than now.   As we put our full attention on our clients, I believe we'll have plenty of opportunity to help companies through this tough economy.

Tech~Surf~Blog:  What did you think of a certain Silicon Valley tech blog that shall remain nameless running a story saying that "DEMO is in trouble"?  And what's been your take on the media interest in general that's resulted in your decision to pass the baton?  

Chris Shipley:  Honestly, I don't think much about it at all.  DEMO isn't in trouble; it's a strong brand that continues to deliver value to its customers.

Your question implies that last summer's market noise drove my decision to step down from DEMO, which is not at all the case.  I'm not leaving DEMO so much as I am going to a new and exciting opportunity.   

You know, there's a lot of "Inside Baseball" in the blogosphere and in Silicon Valley. I've really never been a big participant in those conversations because I don't find them particularly relevant to what I'm trying to do: work with young companies to help them deliver great products to customers who value the relationship with that company.  The vast majority of those customers don't care who launched what gossip about whom.  They care about solving real problems effectively and cost-efficiently.  So, it seems a much better use of my time to listen to the broader market rather than the echo chamber that the Valley can too often be.

Tech~Surf~Blog:  How long have you known your designated successor, Matt Marshall of VentureBeat?  How influential were you in his selection as your successor?  DEMO has stated it plans to delve into "deeper topics."  Will the fact that Matt has a Ph. D. in government mean the event will try to appeal more to policy wonks and academics?  Or what does that portend for the brand, really?

Chris Shipley:  I met Matt as he was founding VentureBeat in 2006, and immediately recognized him as a smart, ethical guy passionate about entrepreneurs and the venture ecosystem.  When I finally made the decision to step down, IDG asked me to help identify my successor and I immediately thought of Matt.  I approached him in the fall and worked closely with both VentureBeat and IDG to make the deal happen.

By "deeper topics," I think Matt's saying that the combination of the live event (DEMO) and the online media property (Venture Beat) creates the opportunity to continue a conversation across the two forums.  The DEMO events cover only about six days a year.  Now, with VentureBeat, DEMO can be a 365-days-a-year community, and that, fundamentally, will allow the conversation to dive deeper into themes and trends.

You know, I don't see Matt as a policy wonk or academician so much as I view him as a thoughtful, hard-working journalist.  I think he'll bring that energy and integrity to the DEMO event, infuse it with his own style and interests, and ultimately make the event his own.  That's what I hope for him, for DEMO, and for the DEMO community.

Tech~Surf~Blog:  How much time will Matt devote to DEMO versus running his own company (which isn't even three years old yet)?  How much time did you personally devote to DEMO versus running your own longstanding firm, Guidewire Group?

Chris Shipley:  Ultimately, that's a question for Matt, so I'll leave it to him to answer.  DEMO is, however, a big job and it is time consuming.  Like every other entrepreneur, I had to get smart about how I spend the limited resource that is my time.  I think I was able to do that reasonably well.  Ultimately, though, I determined that the exciting and energizing work ahead for Guidewire Group is work I want to be dedicated to full time.  And that's what drove the decision to step down from DEMO.

Tech~Surf~Blog: As DEMO's executive producer, it's no secret you travel a lot, worldwide, to meet one-on-one with startups.  Did this demanding travel schedule have anything to do with your decision?  Or did other aspects of doing the same thing for 13 years enter in?

Chris Shipley:  I love the travel because I love meeting entrepreneurs in their business environments, no matter if it's an office in Mountain View or one in Taipei or Madrid or Adelaide.  It's critical, I think, to understanding local market constraints and opportunities.  And it puts Silicon Valley in appropriate perspective.  Guidewire Group has international reach and international clients.  It is, in no small part, what differentiates us from other analyst firms.  So, I don't think the travel demands are going to change very much, and I'm not sure that I'd want them to.

The subtext of the question, really, is "what drove you from DEMO?"  It seems people want the "real story" behind my departure.  The true and remarkably non-salacious answer is "nothing."  DEMO is a great property.  It is a tremendous platform.  And it has been an honor to oversee this event and work with so many passionate entrepreneurs over the last 13 years.  DEMO never got boring, and I am not tired of DEMO, or run down by the travel, or discouraged by competitive or even economic pressure.

I'm not leaving DEMO so much as I am going to a great new challenge: building Guidewire Group into a world-class analyst and advisory firm, focused on early-stage companies that, at times of transition and critical decision, need a fresh perspective to help form and validate their strategies and positions.  Working intensely to help startups succeed.  What could be more fun than that?

Tech~Surf~Blog:  What's your take on the health of the technology startup mindset?  Has it changed with the recession, now increasingly a worldwide one?  Have you observed differences, now or over the years, between U.S. entrepreneurs and those in other countries?  Is there a reason more non-U.S. startups seem to be increasingly pitching at DEMO conferences?

Chris Shipley:  Are you testing my ability to parse a multi-part question? 😉 This is, without question, the deepest recession in the technology market I've experienced in the 25 years I've been covering the industry.  It is affecting every company, not just one over-inflated sector, and it is global in scale.  Without question, the recession will cull the flock. Companies that lack the resources, leadership, and vision to manage through this crisis will go away.  And those that are just a little bit smarter, a little bit faster, a little bit more courageous will win the day.  That's true whether they are in Silicon Valley, the United States, or in any other part of the world.

I used to see a pretty big capabilities gap between U.S. and non-U.S. technology entrepreneurs.  That gap has closed pretty dramatically.  While there are still many cultural and business structural differences that separate U.S. and foreign entrepreneurs, I think I could argue successfully that the barriers that non-U.S. entrepreneurs face are exactly the conquests that make them smarter, more adaptable, and ultimately more successful companies.  Think of it: it's relatively (and I stress "relatively") easy to create a business in an environment that offers all the support and infrastructure an entrepreneur could need. It's a whole lot harder to do that same work without the support systems. So a company that is successful without the support is, arguably, going to be very successful when given the full comfort and care of a nurturing environment like Silicon Valley, even if it is also more competitive.

We consciously went looking for non-U.S. companies to bring to DEMO for exactly that reason.  This is a global market.  Competition can come from anywhere.  Great new ideas aren't bound to Silicon Valley. I've tried to reflect that in the DEMO lineup.

Tech~Surf~Blog:  Please tell us about Guidewire Group.  How many employees do you have?  Who are your clients?  What is your mission?  And what if anything will change about Guidewire Group now that you've stated it will become 100% of your focus, once you transition fully from your role at DEMO after the fall 2009 event?

Chris Shipley:  Guidewire Group is a global analyst firm that works with early-stage companies to effectively build and execute their business strategies. We've identified opportunity in working with young companies at key transition points, to develop and deliver business strategy, monetization plans, and market validation.  Through custom projects, retained analyst services, events such as Innovate!Europe, and Guidewire Studio, our exclusive in-residence program, we're doing the work we love most — helping startups thrive.

We work with a range of clients, both startups and large companies that want to build their relationships with early-stage companies.

We are a small team today, although I suspect that will change a bit over the next year.  We have so many ideas that we want to pursue, and with full focus, time, and passion, I know we'll be able to bring the best of those ideas to life for the benefit of our clients and community.

Tech~Surf~Blog:  Many thanks for taking the time, Chris.  Best of luck in the next, exciting chapter of your career.  And I'll see you at DEMO '09 in Palm Desert.  I'm so looking forward to that opening reception Sunday night…

Chris Shipley:  Thanks, Graeme. I really do appreciate your support. See you in a couple of days.

Photo credits: 1) DEMO PR photo, 2) my own photo as I left DEMO '08, January 30, 2008.

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