How to become more offensive

Two weekends ago I listened to the Tim Ferriss interview of Chris Sacca. Sacca is an early-stage investor in companies like Twitter, Uber, Instagram, Kickstarter, and many more. He's a fairly well known dude. The best audio I've ever heard from him was of him crushing Alex in the Startup Podcast, where he perfected Alex's own pitch for him because Alex was too nervous, and then told him it was a horrible idea. 


In the Tim Ferriss interview, Sacca explained why he moved away from Silicon Valley. Sacca moved to Lake Tahoe at what many would have considered the absolute worst time for him to leave the Valley. He had just lost a ton of money, he was still relatively young and unknown, and he was leaving the most connected area in the world for software startups and investors (aka his job). 


While Sacca was living in Silicon Valley, he had to be defensive with his time. He constantly had people asking him to grab a cup of coffee, to hear their pitch, to give them feedback, or to attend an event. All of his time got sucked up by other people. Even if he said no to the obvious events and people that were a waste of time, his time still got consumed by "legitimate" events and meetings with people he knew and trusted. He was just too connected. While he was being defensive, he found that he wasn't actually getting anything done. 


Part of the reason Sacca moved away was to get the time back, so he could be more purposeful with what he did. He called it, "playing offensive." Instead of constantly defending your time, how can you make space in your life to move to a purposeful offense. If you had more time, what would you do with it? What's your highest and best use? 

Lake Tahoe is around three hours from the Valley. That turns out to be the perfect response to people asking for coffee, drinks, or time. Sacca still said yes, he just told them they needed to travel to him. It was the perfect filter. Most people won't be willing to make that type of commitment. So only the most serious people followed through on the trip out there. 


With his new found time, Sacca pulled himself out of dept. Doubled down on startup investing and advising, and is now running what might be the most successful investment portfolio in history. He's crushing it. And he points to figuring out how to "play offensively" as one of the most important factors. 


Since hearing this podcast, I've been thinking about this a lot. I'm very defensive with my time. I have a never ending stream of meetings, requests for time from clients, requests to pitch from prospects, meetings to explore partnerships, networking events to attend, etc. Never-mind the emails that go with all of that, the commute, and trying to find time to workout. 


I'm guessing I'm not alone. I can imagine you have tasks and activities that make you defensive with your time. I know you have emails, meetings, and I know each role has it's own set of tasks that take up time, but aren't the "core" way that you think you add value. It could be as trivial as time entry, or it could be a regular report you need to put together (ems), a pull request (devs), a regularly scheduled Twitter post (marketing), or something else.  (I just assume that the designers love everything they get to do.) 


We all play defense. It sucks. But it's certainly part of the job when we work as a team. As we continue to grow, the more defense we will all have to play. So how do we handle that? 


At the last Monday morning meeting at DeveloperTown, Aaron Lerch shared some of his strategies for how he manages some of his time and attention. It included tips for email, Slack, meetings, and the dangers of multiproject multitasking. (Side note, I just changed my preferences to disabled emails from Slack. Thanks Aaron!) 


As for me, I'm not sure yet. I've been thinking about it for two weeks now. I don't have the answer yet, but I have some ideas. Here's what I'm doing to try to become a bit more purposefully offensive with my time: 
  • I'm going to reread The Effective Executive by Peter Drucker. I first read this book over ten years ago. I remember the themes, but not the specific details. I think it's time for a refresher. The basic premiss of the book is that all knowledge workers are executives. And executives need to prioritize effectiveness over efficiency if they want to be successful. 
  • I'm going to only check email a couple times a day. While that turns out to be very difficult to do in practice, I'm trying out a new tool called Handle that I think will help me do it. It integrates with Gmail, and has a view that completely hides your inbox while still allowing you to work on tasks and priorities. I've been using the free version for a couple of days, and so far I really like it. I hit inbox zero for the first time in over two years, and I have a clear list of to-dos that have been prioritized and assigned due dates. 
  • I'm going to try to be more purposeful with my days. I'm planning to start each day by listing the top three to five things I want to accomplish that day. And then my plan is to not leave until those tasks are done. If I can't manage to that effectively, I'll shorten the list to the top one or two things. My goal isn't to end up staying at the office later, but instead to train myself to remain focused on those goals throughout the day so I become more protective of my time to actually get them done.
  • I'm going to experiment with sending my peers a short email status each week. No one has asked me to do it. But I think if I can come up with weekly goals, it will help me figure out what my daily goals should be. I'm thinking a short list of bullets - nothing fancy. If I have to take the time to report progress to my peers, then I think it will help me remain focused on those top priorities. Ideally, most of what I'm reporting on each week should roll up into the larger plans we set as a management team. 
  • I'm going to start to ask for help more frequently. I don't need to do everything myself, and in many cases I'm not the best person to do certain tasks. I'm going to try to be more purposeful in handing off tasks and responsibilities to the people who are best equipped to handle those tasks. This is very difficult for me. I suspect it's difficult for all of us to ask for help, and that none of us is doing it enough.  
So that's my starting plan for my new offense. I doubt I'll stick with all of those, but hopefully I'll make some progress in figuring out what works for me. 
If you have some techniques you use to better manage your time/attention/focus, you're welcome to share it below. 

Advisors and Board Members

As a partner in DeveloperTown, I have an interesting role when it comes to our clients. Part of our pitch to our clients is that we are more than a vendor - we want to be a partner. In many cases we want to have skin in the game in the form of an investment, but even without an investment we really want to play a leadership role when it comes to technology and determining product-market-fit. Most of the time, this leadership or advisor role is informal. By choosing us as a technology partner, you get some portion of our leadership team engaged in your business (for better or worse). However, at times, it can be unclear how much of an advisor our client is expecting and/or looking for, and how much we are prepared to provide. When things are informal, there’s a chance for missed expectations. I hate mismanaged expectations. So occasionally, it makes sense to formalize the relationship so everyone’s on the same page. ...

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Why does an RFP process lead to increased cost? Without discussion of the many tradeoffs noted above, there’s no room for the technology team to recommend alternative methods to accomplish the end goals. Ideally, you’d like to find a team to help you solve a problem. Instead, most RFPs tend to lead to teams implementing a given narrow solution. Which assumes the problem is fully understood and adequately solved by the submitted proposal. It costs more to be wrong and have to go back to first principles than it does to move in a more exploratory way at the onset where you continuously question core assumptions and validate those assumptions over time as the project unfolds.

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A project case study

Last summer at DeveloperTown, we chartered a project to have Spencer (one of our interns) along with Chris (acting as product owner and tester) build a new product for an existing client of ours. The work was a bit speculative, but low risk since Chris and I really felt like we knew what the client wanted and needed. Chris and Spencer used a fairly standard vanilla scrum process – leveraging Pivotal Tracker and some other basic tools – to deliver the foundations of the product. Every two weeks or so they would get together to discuss stories, progress so far, and feature tradeoffs. In about three months, they had all the high-level features implemented. ...

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The MVP Reading List

I regularly get asked for book references. From employees new to DeveloperTown, to founders who walk in the door and aren’t sure where to start, to people who look at what we do and how we work and ask how we figured all that stuff out. Some of it we figured out, much of it other people figured out and wrote down. We were smart enough to read it, apply it, and adapt it to the way we work. You can too.

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