Uncommon Interview: Bob Walsh, Digital Entrepreneur

I hate most interviews, and I think everyone else does too. They’re rarely actionable or insightful.

This interview is uncommonly different. In the last interview Peldi Guilizzoni (Balsamiq Studios) gave detailed advice about how he earned almost a million dollars in revenue in his first year of operation.

In this installment we hear from startup expert Bob Walsh, whose many works for startup founders include:

• Blog: 47 Hats
• Podcast: Startup Success
• New book: Web Startup Success Guide
• Classic book: Micro-ISV: From Vision to Reality
• Online guides and support network for founders: StartupToDo.com

Below Bob digs into his years of experience living with, mentoring, and thinking about tiny startups to tell us what’s important for a founder starting a company today.

Q: You’ve stated that the goal of both your new book (Web Startup Success Guide) and your new tool for entrepreneurs (StartupToDo) is to double an entrepreneur’s chance at success: Increase from 10% to 20%. That’s a terrific goal — and it certainly seems plausible — but to what do you attribute the other 80% of the risk? Luck? Timing? Ideas? Tenacity? What are the big killers lurking for the new startup founder?

I think the big killers of newborn startups lurk mostly inside the heads of founders. First and foremost, succeeding as a Digital Entrepreneur (my new catch-all keyword for traditional funded startups, unfunded startups, microISVs, indie game developers and content creators like bands and authors. Like it?) means you need to be the most stubborn S.O.B. you know. Perseverance is the single most important attribute you need. Pick any 5 successful software companies you’d like from one-person microISVs up to the largest and trace how their market focus, product, marketing etc. has zigged and zagged from inception. That’s staying in the game until you find what works.

Editor’s note: Most people think “perseverance” means “being so confident in your ideas that you don’t change your mind even when there’s reason to doubt.” But Bob points out that companies are fluid, and those who survive are stubborn about building something good, not about any one idea.

Another reason DE’s turn back is it’s lonely out there. Whether it’s creating a software app that you’re going to build a global one-person business around, or giving away the Science Fiction stories you write as you build your community so you can launch a book, this is lonely stuff few back in the safe (ha!) warrens of working for some large company would dare do.

Q: You spent two years working on StartupToDo before bringing it to market. Clearly it’s the culmination of your years of experience with startups — writing about them, mentoring them, promoting them, and watching them grow, shrink, live, and die. How were you able to convert this knowledge into a software product? What aspects of building a company can be encoded in this manner, and what’s still outside the realm of “how-tos?”

When it comes to software, you as the developer have got to really understand both the people who have the problem you want to address and the problem itself. Now maybe you get this understanding working for a company, writing software for clients, or because you are as the saying goes scratching your own itch.

Between the various things I’ve been doing and my own efforts I started noticing just how much time in this business goes into context work — all of the stuff besides the core of what your are building — and how hard it is, how much you have to sacrifice, especially if you are bootstrapping. I realized that startups reinvent hundreds of wheels and that’s an awful way to build businesses. Then one day I read a comment on Darren Rowse’s blog by a guy who created a point system to keep himself blogging, consistently, and motivated and I was electrified by the idea putting “actionable guides and discussions” together with “measurable progress you could see, share, and compete with in a friendly way.” It took about a year and a half to start learning rails, go off on a tangent (the teachingsells.com approach) get back to learning rails, go off on another tangent (Adobe AIR — good stuff, but not a good fit), get back to learning rails/JS etc. sufficiently well to — with a lot of help — code StartupToDo.com.

There’s a lot of value being able to talk about current business issues with your peers and hearing what other people recommend (See the Business of Software Forum and Answers.Onstartups.com), and getting a solid overview/education on one of the many aspects of this business (see Microprenuer Academy). But one of the unfortunate aspects of “forumizing” is it’s easy to substitute endless online talk for concrete action. I’ve really tried to build the first two big chunks of value in my startup to create what I call focused, actionable discussion.

To Do’s are not enough. Hopefully the Guides at my startup that I and other community members are writing are more than static recipes.

Q: You’re a big advocate for startups using social media because it’s essentially free (in dollars). But it costs a lot in time and effort — another scarce resource. Is traditional marketing and advertising completely dead, or is there still room for it in a startup?

Jason, you’re right: social media marketing takes lots of time. And depending on your startup’s market, traditional marketing (paper spam, email spam, sales visits, shows, conferences, display ads, etc.) may still have some residual value.

But there are three things at work here. First, developed country societies are moving from industrialism where standardized advertising worked to post-industrialism where the Internet empowers people, markets and conversations. Second, the core values that you find among people who came of age after the Internet are markedly different – the ugly corporate truth is traditional marketing and advertising barely influence them while what their personal social networks “think” and how they interact person-to-person (e.g. Zappos) matter far more.

Here’s the third: Few startups (let alone Digital Entrepreneurs) have more money than time. It happens to be a very happy circumstance that we can now translate time via social marketing (blogs, Twitter, Facebook and all the rest) into sales. Unfortunately, developers in general hate to market (social or conventional), hence why I’m focusing on making marketing, especially what you do online, ultra easy as the next big feature of StartupToDo.com.

Q: You’re well-known for promoting David Allen’s Getting Things Done (GTD) system for organization and productivity, and Chapter 8 of your Web Startup Success Guide is devoted to it. How important is “personal productivity” to the success of a startup? We all know people who are completely disorganized yet effective, and others who have everything in order but never seem to accomplish anything. Is organization fundamental to startup success because time is so precious? Or can it just be a distraction?

For 25 or so years when I built software for San Fransisco Bay Area corporations as a contractor, personal productivity was my obsession — the more and better ways I could improve my productivity, the more money I’d make. That’s probably why my first commercial product was a Windows desktop personal task manager.

So far, David Allen’s GTD methodology of getting tasks out of your head, processing them efficiently and tracking your results is the best productivity theory we have, IMO. If you can find an effective, not obsessive, way to apply that, you’re going to have a decided advantage in just about anything you do in this world, including creating your startup.

The key thing about personal organization is it’s very personal. Have you ever seen the shot of Al Gore working on three monitors in his office surrounded by stacks of books, paper, and whatnot? That’s what works for him, with demonstrable results.

Finding/creating the right tools for you to move tasks to results in a consistent manner is what matters, not the ceremony or form you use.

Presently I use Things on my Mac and iPhone to track tasks, Notebook on my Mac to plan in, and SpeakEasy on my iPhone as a way to capture tasks and thoughts throughout the day I can later process. Also, I find Basecamp comfortable when I need to project management with others and checkvist.com an easy way to collaborate on outlines.

Q: You wait until Chapter 7 of the Web Startup Success Guide to talk about the Unique Selling Proposition (USP) that uniquely describes your company’s purpose and niche. Do you believe startups need to determine their USP from the beginning (because it’s vital to defining yourself) or is it something you back into over time (because you have to seek your market position)? In either case, how exactly do you go about defining it?

I believe the Internet rewards original content and punishes unoriginal content, be it software, ideas, or products. If you can’t explain to the market and yourself who your product or service helps how, you’re in trouble. I think that the earlier you can define your startup’s USP the better and recently I’ve found some validation of that approach in what Marc Andreessen and Steve Blank have said about product/market Fit (useful stuff, and yes, I’m writing it up as a S2D Guide!).

That said, the “defining part” is no easy exercise. I wish I could boil it down to a checklist, but there’s more to it than that: your USP depends on what you are bringing to the party. Your experience, insight, opinions, values and abilities define your solution to the problem. One thing I think is true: is it’s an iterative process –the more times you examine your USP, the sharper, more useful, more effective it becomes.

Q: Your book is clearly targeted at web-based software companies, and perhaps even more specifically at software developers. What of this advice is applicable to other businesses, or at least businesses who want a strong web and social media presence? For the non-technical business owners out there, what parts of the book should they still read, and how do they know which of your advice to apply?

Guilty!   :-)

I write/podcast/work for developers who want to build their own software and software companies. Why? Because those are the people I like, and want to help succeed.

But for a while I’ve been thinking that software startups, microISVs, bands, authors, and others have more in common and share more values online than they do offline. Hence the Digital Entrepreneur meme. Neither The Web Startup Success Guide , the Startup Success Podcast or StartupToDo.com are for programmers as programmers — you won’t find a single line of code in the lot of them. So, whether you are or are not a programmer, the stuff I’ve created over the years will have some value for you.

Any questions?

Thanks Bob!  Please leave questions (or arguments!) in the comments to continue the discussion.