image of Five Key Traits that Successful Entrepreneurs Share - Jeff Dennis, Counsel, Fasken Law
Thursday, December 9, 2021

Five Key Traits that Successful Entrepreneurs Share - Jeff Dennis, Counsel, Fasken Law

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Podcast information


Episode Details

Jeff Dennis, author of the book, "Lessons from the Edge: Survival Skills for Starting and Growing a Company” shares the pitfalls of startup partnerships, different degrees of commitment, divergent visions, lack of trust or shared values. He also explains the importance of building out a team protected by established guardrails.

Show notes

Winning attitudes that show up again and again among the most effective entrepreneurs, include:

- They are lifelong learners, perpetually curious.
- They don’t feel the need to be the smartest person in the room.
- They’re able to listen to feedback, seek out information and learn from others.
- They’re good at delegating and helping people reach their full potential.
 -They demonstrate humility and openness.

Key Takeaways

0:00 | A bit of Jeff’s background by way of introduction.

0:50 | Jeff decided to convene a panel featuring the stories of seasoned entrepreneurs willing to candidly share the unvarnished lessons they’d learned through trial and error. The concept was an immediate hit that spawned his book, "Lessons from the Edge: Survival Skills for Starting and Growing a Company."

3:29 | Through the process of hosting panels and researching his book, Jeff learned that there’s a menu of mistakes that entrepreneurs regularly make. Why? Because they’re making decisions with limited resources.

5:30 | The huge success of his book afforded Jeff the opportunity to travel the world, speaking to various business groups, build his network and broaden his horizons. At this point in time, a sequel is unlikely but there are a lot of great come-back stories among the those he profiled.

7:42 | During pandemic Jeff got involved with a number of online groups, including a call that coincidentally included more than a dozen of the entrepreneurs featured in his book. The long-term outcome was pleasantly surprising: They had all experienced noteworthy comebacks.

10:30 | When it comes to fast-growth tech company mistakes, among the most common Jeff sees is poorly chosen partnerships. Mismatched value sets, long-term goals, ambitions and expectations are all liabilities. People very often spend more time interviewing prospective employees than they do vetting co-founders.

12:47 | How passion and naivete ultimately hobble entrepreneurial ventures.

12:59 | Another common mistake? Giving away too much equity. 

14:21 | Jeff’s recommendations for putting the right guardrails in place around your enterprise:
Know who you’re getting into bed with. Kick the tires and make sure you share the same work ethic, values, timeline and commitment. Ask the hard questions.
Put in place a shareholders’ agreement and a conditional framework for vesting (or reverse vesting) to protect against undue loss of equity.

17:05 | Asking the hard questions. Jeff looks at business partners very much like a marriage, requiring a similar level of honesty, vision, commitment, trust and communication. Does your prospective partner fight fair? Know how to compromise?

20:40 | Valuation is a tricky business. Partnerships aren’t necessarily inherently equal. Contributions and value-add can vary significantly and without a clear definition of entitlements over-compensation of one or more partners is a real risk.

22:30 | Jeff reflects on the big question – the one he believes is most essential. Why are you doing this? He believes too many entrepreneurs lose sight of a very simple driving purpose for entrepreneurial endeavors: Providing for our families. 

25:05 | Life Advice: Per Chapter 5 in “Lessons from the Edge,” Jeff urges entrepreneurs to appreciate the fundamental necessity for balance. Sleep, eat properly, exercise, have a spiritual practice of some sort, have relationships. Because at the end of the day, what’s it all for? Money and success don’t hold a candle to fulfillment and connection.

27:20 | Jeff defines some of the traits common among the most effective and successful entrepreneurs, which include:
They are lifelong learners, perpetually curious.
They don’t feel the need to be the smartest person in the room.
They’re able to listen to feedback, seek out information and learn from others.
They’re good at delegating and helping people reach their full potential.
They demonstrate humility and openness.

31:11 | A few thoughts about hiring technical co-founders, the unique skills and liabilities with regard to team building. MVP roles can be dicey and complicated.

34:35 | BATNA: Best Alternative to a Negotiated Agreement. When you go into a negotiation it’s essential to have a Plan B, without which the other party has all the bargaining power. Where do you have to go and if there isn’t another avenue, your answer is simply: Take the deal. If you do have an alternative, it’s time to talk about the options.

37:04 | The Art of Negotiation: It’s not for everyone. Some people thrive on it but others have to study it with all deliberation and develop a toolkit that may never become particularly familiar or comfortable to execute.

37:56 | Jeff shares some parting thoughts about riding – versus fighting – waves. Going with the flow is invariably the easier route. But you also have to stay aware in order to recognize and jump onto that wave. It’s about keeping your eye firmly fixed on that horizon.


“It’s quite lonely at the top as an entrepreneur.” [2:25]

“People very often end up with the wrong (partnerships) and then it’s a mess. It makes it hard to run a business, finance a business, sell a business, grow a business … It’s a disaster.” [11:41]

“Ego is the worst. If you let ego drive you that’s destined to fail. I see a lot of that.” [13:54]

“If you’re founding a company you’ve got to have that stick-to-itiveness and passion and commitment. And it’s tough. It’s become glamorized to be an entrepreneur (but) it’s not for everybody.” [14:55]

“You only call in the lawyers when there’s a problem or you’re selling or financing. Day-to-day business? At the end it’s got to be good faith.” [18:33]

“There’s a misconception because of technology that you can start a business with nothing. You can’t. You do need resources. You need more than a laptop. So you need partners because they bring resources to the table.” [20:02]

“It’s lonely at the top. You need somebody to talk to, somebody to work on this self-awareness piece because – at the end of the day – are you going to be happy just because you built a company and sold it? Is that the meaning of life?” [24:35]

“I’ve seen guys make tons of dough and go through five wives and they’re not happy. I’ve seen other people who have nothing and are very happy and content. So it’s got nothing to do with success and money. I don’t think it’s co-related.” [26:06]

“The guy who is able to get something off the ground is different than the person who can sell it and motivate a team of 200 people … I’m not saying you can’t learn it. But who the hell is good at everything?” [29:17]

“Negotiating is a whole other skill set. Not everyone is good at negotiating ... It’s a skill. It’s in your genes. Some people have it and some people don’t.” [35:27]

“What’s the wave here? Decentralization. Gig economy. All these trends – waves – what are they? Let’s ride them. That’s what I look for and when I look at companies I’m looking through that paradigm.” [40:11]

“There’s lots of factors to success, but fighting a wave is not one of them!” [40:32]

Contact Jeff

What is Off the Record with Aram?

Made by entrepreneurs for entrepreneurs. Off the Record is about the journey. It’s about fears, doubts, wins, and devastating losses. It’s about how people kept going no matter what to build their businesses, raise cash and hire the team. Here battle-tested CEOs and VCs share how they jumped out of the airplane and tried to assemble it on the way down.I hope you like it.

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