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" For me, the brightest years at IronPort were without a doubt the darkest years at home. "

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" The experts typically know where the other best-in-the-world talents are currently working and can help you recruit them in with a credible intro. "

" Nothing helps make a leader more approachable than admitting your struggles, screw-ups and behind-the-scenes thinking on hard calls. If the leader makes this a priority, the whole company will be more open and methodical learning from failure. "

" I don't like sweating the details, and I'm pretty disorganized. To be a better leader, I need to stay on top of these shortcomings, and being reminded really helps. "

" Trust leads to approachability and open communications. "

" Your happiness is at the intersection of your passions and learning from great people. "

" One of the stated values at IronPort was 'work/life balance,' but I wasn't living it. I was rarely home. And when I was home, well, let's just say I wasn't particularly helpful or cheery. "

" It's just not possible to be a real partner if you aren't materially participating. I believe even the busiest business owners must drive a carpool, pack a lunch, help with homework, make a breakfast or dinner, and consistently attend school events. "

" Feedback for leaders is often nuanced and difficult to deliver. That said, hearing you are passive-aggressive from 10 different people described 10 different ways becomes hard to ignore. "

" The best board members aren't elected by default. CEOs that set themselves up with their choice of board member - which means getting more than one term sheet and doing extensive reference checking - are better off. "

" An approachable and authentic CEO is essential to fostering a high-performance, open communications culture. "

" I see many founders waste too much time trying to work their networks and/or ultimately settle for mediocre but available candidates. You will definitely have to interview hard for cultural fit, but the best talent isn't cheap. "

" The first day, week and month of an employee's experience carries a lasting impression. "

" At the core, coaching authenticity is complicated - some might say impossible. Telling someone to be authentic sounds pretty low calorie, especially to a founder plowing through a list of product and operational goals. But it's important. "

" All great pitches have a few things in common: the founder/team is wicked smart, the idea is big and a breakthrough, and the market is potentially enormous. "

" When a team has to work over a weekend, make a high priority of being there as well, even if it's just to stop by and buy them a meal to show your appreciation. "

" Part of the magic of a startup is the fear of death. You have only so much money in the bank, and if you don't get to the right milestone before you run out, then the company goes under - it's over. "

" I wouldn't suggest that being resourceful has anything to do with doing something illegal or unethical, but I've definitely noticed a pattern of being 'creative.' "

" When my co-founder and I first had the idea for IronPort, an email security company, we triangulated a list of the 20 most relevant people in email - former CEOs, open source technologists, investors and thought leaders. "

" Most companies don't have a good mechanism to give the CEO real, honest feedback. "

" At Andreessen Horowitz, we talk about the notion of being 'too hungry to eat.' That's to say, we often see startups that are so entrenched in the product that the founders forget they need muscle to grow. "

" It's important for a leader to hear about his blind spots on a regular basis so working on them is periodically top of mind. "

" Working at a big company sucks - avoid it. Smaller companies are 10 times better for learning. "

" Hold at least one all-hands meeting every quarter and, to underscore the startup's team concept, make sure at least one additional executive joins you in leading the meeting. "

" While there's no substitute for real experience, I believe it helps to hear and share stories of resourcefulness in action - almost like case studies in school. "

" Whatever vocation you decide on, track down the best people in the world at doing it and surround yourself with them. "

Surround Yourself

" Be generous with your time and money - it has an amazingly fast payback. Be in the moment with everyone you love - and this frequently means tuning out work completely. And drive slow in parking lots. "

" As a decision maker, you rely on information being passed to you by the people who report to you. As the CEO, however, you cannot rely solely on this information. You also need to 'dip' down into your organization and learn directly from employees at all levels and virtually all skill sets. "

" The thorniest business problems will surface at the board meetings, and the different, sharp opinions help to better explore the poles of the arguments to make better decisions. "

" Being on a board is not just about showing up for the meetings. A board member needs to materially contribute to the success of the business. "

" As a first-time CEO, I wasn't sure if I would scale to run IronPort long-term. But I wanted a legitimate shot at it. "