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.
— Scott Weiss
An approachable and authentic CEO is essential to fostering a high-performance, open communications culture.
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.
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.
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.
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.
Most companies don't have a good mechanism to give the CEO real, honest feedback.
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.
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.
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.
Whatever vocation you decide on, track down the best people in the world at doing it and surround yourself with them.
The first day, week and month of an employee's experience carries a lasting impression.
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.'
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.
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.
One of the rookie mistakes first-time entrepreneurs often make is to be too guarded about their idea - in fact, many will actually spend their first $25,000 on patent lawyers without ever fully vetting their product.
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.
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.
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.
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.
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.
Working at a big company sucks - avoid it. Smaller companies are 10 times better for learning.
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.
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.
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.
Trust leads to approachability and open communications.
It's really hard to break through the clutter and get the attention of the top investors, as they typically only look at deals that come in from a warm, credible referral. There's absolutely nothing more credible than getting an endorsement from a well-known subject matter expert who has already put their own money into your company.
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.
For me, the brightest years at IronPort were without a doubt the darkest years at home.
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.
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.
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.
Developing a good, healthy culture is extremely important at a startup. Culture reflects the essence of a startup's operation because it directly affects the success of a company's hiring practices and overall strategy.
Your happiness is at the intersection of your passions and learning from great people.
As CEO, I had a standing 30-minute meeting every Monday to greet and connect with new hires.
