Don't Give Up the Second Time Around - David DeWolf

Don’t Give Up: If the Third Time’s a Charm, Second’s a Dog

After 90 minutes I was ready to pull my hair out. “Let’s try that again. I think it could be tighter.”

Mike was right. Everything I said seemed like it was coming out wordier than it needed to. I wanted it tighter and I wanted to put a finer point on my message.

“I’m not this much of a bumbling idiot, I promise.”

Mike Manion and I were in the studio together for the second time. Having a co-host for “Steal My Show” was supposed to make this easier and more engaging.

It didn’t seem to be working out that way. Maybe the opposite.

Mike saw my frustration.

“It’s not uncommon for the second time around to be harder than the first. The first time around you’re not thinking about it. You’re just going with the flow. The second time around you’re trying to replicate the results and fix what you didn’t like. By the third time, you’ll be perfecting it.”

This got me thinking. Maybe there is something to “Beginner’s Luck.”

And then it hit me. How many people give up after the second time around, simply because it’s harder than the first and they figure they are “not good at it”?

Here’s my theory. The second time you do something, it takes about twice the time or effort of the first. The third time, on average, it takes half.

Don’t give up. Persevere and perfect your art. It will pay dividends in the long run – in more ways than you expect.

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4 Steps BEFORE Building Your Startup Team - David DeWolf

4 Steps to Take Before Building Your Startup Team

The excitement and passion were high. Karen and Jose couldn’t stop talking. No matter how much time we had together, it was apparent that neither one thought there was enough time to cover everything.

Having just raised capital, they had a million ideas about how they might take their (rather immature) product to the next level. They wanted to discuss several hires they were about to make and talk a bit about how to set up their organization.

After 15 minutes had passed, I barely snuck in a question. “Can you back up? I think I missed something. What’s your vision”?

Karen paused. Jose quickly piped in, but he failed to answer the question. He simply spouted a few more ideas and it was obvious to everyone in the room that he missed the mark.

I asked a follow on. “Let me ask it this way, what is it that you’re ultimately trying to become? Describe your company five years from now. What does it look like? What have you accomplished?”


“Okay. Twelve months from now? How are you different from anyone else in your space?”

More silence.

“Describe your product. Don’t tell me what it does. Tell me why it’s different.”

Finally, an answer. Unfortunately, it was all about the cool technology that had been developed and was unlike anything else in the market. A recipe for disaster.

After a few more questions, it became apparent that the founders of this company had no idea where they were going and how they were going to get there.

All too often I see product companies with nothing more than technology. No vision. No strategy. Nothing but an idea.

I advise first-time CEOs to be deliberate about creating a business by following these steps, each one of which builds upon the other.

1. Develop your core ideology.

What is your mission/purpose? What are your values? Be explicit, this is the foundation of your business and will seed the culture of your organization.

2. Develop your vision.

What is it that you want to become? Where are you going? Get crazy and define that “Big Hairy Audacious Goal”. This will inform your strategy and motivate your team.

3. Develop your strategy.

How is it that you intend to be different? What is your unique advantage? Competing on the basis of being better, or cheaper (obviously), will lead to commoditization. Be deliberate about creating a differentiated strategy.

4. Develop your structure.

How do you need to structure your organization in order to deliver on your strategy? Hiring people without an organizational strategy is a colossal failure waiting to happen.

I was shocked that Karen and Jose raised significant capital with so much ambiguity. While it’s not incredibly common any more (1999 has come and gone), there are plenty of entrepreneurs, intrepreneurs, and organizations that have gone straight from “an idea” to “a product” to trying to build a team. Doing so creates mass confusion and is a recipe for disaster.

A two- to three-day pause can solve all of these problems. Take the time to develop your core ideology, vision, strategy, and structure and you’ll be ready to build your team in no time.


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Episode #003: The Power of Vulnerability [Podcast]

This week, we discuss the power of vulnerability, whether it’s in the office or your daughter’s bedroom. I’m joined by cohost Mike Manion, Area President of Convene’s Mid-Atlantic region and a frequent host on various radio shows and podcasts.

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I share the story of how I learned about how powerful vulnerability is…the hard way.

Steps for you to tap into the power of vulnerability:

Admit your mistakes. Be transparent with your thoughts and feelings with others. Encourage  and help others share in that same vulnerability.

Vulnerability is a leadership tool that we’re afraid of. It’s so powerful, because it’s human and real and authentic. By being vulnerable, you demonstrate trust. You show that you’re in it for the mission, as opposed to for yourself.

When we’re real and authentic, we’re able to motivate and lead much more powerfully. It has taken me a long time to learn how to really embrace the power of vulnerability and use it consistently.

Your challenge: be vulnerable this week.

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Question Your Leaders and Dive in - David DeWolf

Question Your Leaders: Why It’s Better to Dive in than Walk Away

A couple of weeks ago I found myself perplexed. A leader that I have profound respect for – and consider a mentor – had approached me about doing business together. This is someone I look up to and would have loved to work with. Of course I couldn’t wait to say yes.

As our conversations continued, I was put off by a couple of details associated with the deal. I couldn’t understand why this person would conduct business this way. Something wasn’t adding up.

Luckily, I’ve been in this position before and have learned the hard way not to leave my questions unresolved. Ignore the “gut feeling” and you risk everything from being duped to ignoring a simple warning sign that motivations are misaligned. Both can end in disaster and destroy a relationship, regardless of how much you trust the person you’re doing business with. On the other hand, simply walking away might be safe but prevent you from a unique opportunity.

So, I dove in. I had the hard conversation. I asked about my concerns and expressed my fears. I spoke to a mutual friend that had entered into a similar arrangement and he helped me understand the reasons why these details made sense, at least for this leader and in this situation. There was information that I didn’t understand.

Only time will tell whether I fully embrace the approach. I’m not convinced that it isn’t extreme. That said, I understand its purpose and am open to the reality that I just might learn something from someone who knows more than I do. Regardless, I’m not able to move forward, with peace of mind, with an opportunity that has the potential to be monumental.

How often do you question your leaders? Do you dive in to understand, or do you simply walk away or risk getting burned?

The reality is this: Leaders often have more context and information than you do. Seek to understand before making a judgement. Leaders don’t expect you to follow blindly. Seek the clarifications you need to be to be comfortable. Leaders are human. They make honest mistakes. Strive to be transparent about your hesitations, perhaps they are wrong. To get ahead, you have to take smart risks. Don’t risk getting burned, risk the hard conversation. Learn to live an integrated life with humble confidence. Get it Now Join the Discussion

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Balancing Strategic Planning and Messaging - David DeWolf

Balancing Strategic Planning and Messaging [Graphic]

A few years ago, we spent a great deal of time at 3Pillar talking about who we are, what we do, and how we do it. Though we had always known and agreed on 80% of the answers, I’ve found that the 20% can really shape your business and provide strategic direction.

There’s a radical balance that must be struck between getting these answers right and driving these efforts to completion.  There’s a tendency to seek perfection and wordsmith to death.  On the other hand, significant thought does need to be put developing your core ideology, strategy, and messaging.

Many articles have been written on core values, purpose, mission, and other idealogical and strategic concepts and I don’t intend to rehash them here. (If you’d like to do some reading, take a look at HBR.) Here are some tips that I would offer in regards to these efforts:

Focus on the meat and potatoes. Keep things simple. Be explicit. Consider them living documents. Be proportionate to your maturity.

To read about each of these items, see the post I wrote in 2010.


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