Business leaders and investors need to embrace the unknown
Serendipity is not the same as luck. Rather it is a way of thinking, behaving and exploring that allows for possibilities that you did not know were available.
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Why I continue to help inmates get a fresh start as entrepreneurs
Defy Ventures at Donovan State Prison changes lives. But training and education don't come for free.
When and how much to invest in startups?
The puzzle of money, and valuation is fraught with nuance.
Founders must navigate the critical trade off between wealth and control
At some point, most entrepreneurs will need to choose between growing their company rapidly by relinquishing control or retaining power at the cost of limiting the ventureās potential.
How to be a truth teller at work and not get fired
Focus on why the proposed plan in its current form is not good for the company, not why your boss is wrong.
Why startups shouldnāt skimp on hiring a legal eagle
Picking an attorney to guide you through VC deals is not the luck of the draw.Ā It matters.
Is being nice a no-no when negotiating a deal?
Some fear they will be exploited if they show kindness, but others say a sprinkling of gratitude in the world of entrepreneurship and deal-making can improve your negotiating skills and...
For entrepreneurs: A story about risk and reward from Broadway
Being in the right place, at the right time is not something that a VC can model or that an algorithm can calculate.Ā Ā
How to play the startup game
Every founder who has had the āmonster successful exitā will it that somewhere along the path, they caught a lucky break, an unknown that could not be foreseen but that...
What the game of chess can teach startup founders about decision-making
Not every chess game ā or business deal ā is played the same way.Ā Some are high speed and over in minutes, others are classical and take hours or even...
The art of persuasion for entrepreneurs
You might have a great idea, product or service, but you still have to get someone to buy it.
Why entrepreneurs need to think like magicians but not trick people
Think like a magician means trying to create a moment of the willing suspension of disbelief, that real feeling when the customer knows they have been listened to and are...
If you have a good story and a good company, the money will find you
But deal-sourcing has changed.Ā Expect to get called by more VCs looking to find what you are up to.
CEOs canāt do it all. Hereās how to learn how to delegate
It's a team effort so learning how to balance is key.
We donāt speak up because we donāt think it will make any difference
It is deadening to be in a situation where you are ignored. The feeling of helplessness, it wonāt make a difference, the boss canāt hear me.
Just because you want to lead doesnāt mean you should
There is a correlation between ambition and leadership skills, or lack thereof.
Delegation is a skill many CEOs fail to master
The desire to micro-manage, especially in areas where you are clueless, is hard to kill.
When friends and family invest in your company
They are investors and should be treated as such.
Why do people talk to themselves in the third person?
Sometimes working through a problem by talking to yourself is a good way to find a solution or teach yourself something.
Why entrepreneurs need to focus on gratitude when negotiating a deal
Each side has to āneedā each other in some way ā and to acknowledge that need. Not just product market fit, but also culture.
Why I am ing on personal resolutions for 2025 ā and why you might want to do the same
My goal for 2025 is not to change the world, but to be a better part of the world.
Why you might want to consider a sabbatical ā or not
There's a chance you won't come back to work or your employer won't want you back, but the reward of a renewed outlook often worth the risk.
Does using AI to talk to your employees work?
Bosses who use AI to be more efficient and save time in communications in many cases face ā no surpriseā backlash.
How does being a second choice affect your sense of belonging at work?
It can either motivate you to excellence or you can fade, fold and leave the company.
So you want to own a fishing lodge ā¦
Here's one entrepreneur's journey to reaching his dream.
Why entrepreneurs should watch out for the ālocal maximumā
Judah Taub, author of "How to Move Up When the Only Way is Down," offers an interesting way to think about achievement based on his experiences in the military.
What entrepreneurs gain from looking within
It is never only the technology or the total addressable market, it is also who you are, how you think and what is inside that is important.
So you wanna be a venture capitalist?
Here are the questions you need to contemplate, says a general partner at NFX, a well-known venture fund.
Thinking about risk vs reward as an entrepreneur
What is your bet actually worth measured in cost compared to its potential value?Ā Ā Ā
The customer is always right ā except when it comes to airline service
Every CEO knows that telling your customer the truth quickly, even the bad news, is the absolute baseline for customer retention.Ā
What does how we write tell the world about ourselves?
A personās writing can reveal more than they may care to share.
How a personās āemotional quotientā can make or break deals, your firm
Emotions rule the day.Ā Emotions alter your sight and hearing. But they also influence how you run your company.
Why entrepreneurs make bad blunders, failing to see the truth, over and over again
Why is it so hard for us to make good decisions?
Advice to young entrepreneurs: Yes, things change in life and work ā and that is both frightening and exhilarating
my experience with young people is that though they know very few decisions are fatal, they are obsessed with getting each and every one of them right.Ā Ā
A summer reading list for entrepreneurs (but itās not what you think)
Every entrepreneur needs to broaden their personal perspective, leave the comfort zone of tech-talk from time to time and read.
Why traveling back to your past ā to where you started ā is so powerful
Sometimes, to write a new chapter in your life, you need to go back to your roots
The skills that matter the most in the C-Suite
Beyond having a grand vision, a successful CEO needs to have empathy and understanding to make that vision a reality.
Technology principles every leader needs to know
A CEO needs to understand why they need to build a āplatform,ā not just an application.
Donāt reach out for an investment in your startup if you donāt send a callback number
If you want an answer, send a cell number.Ā Especially if you are asking me to write a check.
Risk and reward: Does the next generation know what it takes to succeed?
Is the discipline and drive from one generation transmitted to the next, and if so, in what way.
When is it time for a CEO to turn over the reins?
As an entrepreneurial concept, knowing when to step down is a classic one, visited time and time again by a board of directors ā when there is one.
Entrepreneurial lessons gleaned from road trips to New York
Learn to be flexible, always have a Plan B and when you're networking, don't drop the ball. Follow up.
The gratitude and lessons learned from volunteering
Why becoming a companion sailer through the Challenged Sailor Organization means so much to this entrepreneur
Finding the bottleneck in your business ā and fixing it
The assignment: Train a monkey to stand on a pedestal while it juggles flaming torches. This puzzle has been articulated by both Astro Teller, genius at Google X, and also...
It pays to understand finances – in both your business and your personal life
Financial literacy.I can’t define it exactly but I know it when I don’t see it.Try this on for size. In 2022, according to the FBI Internet Crime Complaint Center, there...
The pride that comes with figuring things out yourself
You all know what DIY stands for — do it yourself.Mike Norton, a Harvard professor, has written about DIY, and his key insight is that “building or creating something yourself...
Life after prison: Helping inmates get a fresh start as entrepreneurs
Maybe you can’t go home again, but you can go back to prison.In January of 2016, I — along with Taner Halicioglu, Mark Bowles, Tom Tullie and others plus a...
Why you should meet these 9 small businesses trying to grow and succeed
Recently, I was a judge at a pitch presentation of 14 companies that had gone through a 90-day, 12-session training program developed by Founders First Community Development Corporation. The program’s...
Why you really don’t need an NDA to share your pitch deck
The pitch deck. Does it have 52 cards and two jokers, is it the deck of the Titanic or is it the key to the universe of truth, fame and...
Lessons I learned from the late Daniel Kahneman
Everyone has idols.When I worked in Hollywood, I wanted to be Frank Capra or Preston Sturgess. When I transitioned to real estate development, I wanted to be Frank Gehry. And...
Is being an influencer a job? A real job?
My wife, Barbara Bry, and I have eight grandchildren age 3 to 10, including a set of identical twins. My beat is entrepreneurship so now is clearly the time for...
Navigating venture capitalists, angel investors, entrepreneurs
Time. Mentor. Network. Truth.I left off beauty because that is in the eye of the beholder. A recent experience showed me the landscape of the entrepreneurial adventure. Let’s meet the...
If opportunity knocks, do you have enough courage to let it in?
During lunch with an old pal, we talked about “opportunity” and how to identify it. Can you see it from afar or only when it is right in front of...
Swimming in the deep end of artificial intelligence
Artificial Intelligence — yada, yada, yada.Sometimes the only way to learn how to swim is to be tossed into the deep end. And that is exactly what I have decided...
Looking for advice? A mentor? Avoid these common mistakes
If I wanted your advice, I would have asked for it.I have attended a multitude of s and pitches, and at some point in the program, the value of a...
Skill vs. luck in making deals, running successful ventures
I recently shuttered a failed company. I had raised less than $1 million and was pretty sure we had a winner. I was dead wrong. Bad timing, bad idea, bad...
Real innovation is hard to find
I recently read an article about chaos vs. complexity in the American socio-economic-political system. Stability moving to instability and order moving to disorder. Then I took a nap. Unfortunately, when...
Why having fun is good for the soul
How are you feeling? Series B financing going well, the board loves you, no homeless people camped in your parking lot, excited about the election choices, revenue ramping up, marriage...
Can AI help entrepreneurs make confident – and correct – business decisions?
The average adult makes about 35,000 remotely conscious decisions each day. No wonder you are exhausted by the end of the day. All right, how many of those did you...
Here are a few more 2024 resolutions to contemplate
It is near the end of the first month of 2024, and the wellness gurus, the pop psychology promoters, the financial dart throwers and the tax planning advisers have all...
I’m there for you, baby
Who has the power — the CEO, the Board of Directors or the Venture Investor? You can have door #1, door #2 or door #3, or you can do the...
Entrepreneurial class of 2024: Hope is not a strategy. You need a real, viable plan
A few years ago, I was one of the leaders in bringing the Defy Ventures program to Donovan State prison in San Diego. The rigorous program was designed to bring...
How do entrepreneurs get into the zone? Get into the flow?
All of us, athletes, scientists, bus drivers or nurses, know when we are in the “state of flow,” that magic combination of factors that make it easier to complete the...
Don’t underestimate the importance of generosity in leadership
It’s that time of the year.The curmudgeon in me mostly reflects on the incredible effort by the community of retailers to get me to spend money on stuff I don’t...
Did you hear me? Why it’s important to become a better listener
A few thoughts on listening and one good idea (maybe).I am a junior member in a group of old men (no women, feels a bit like the lunch bunch at...
The human science behind deal-making and your appetite for a loss vs. a gain
Let’s talk about decision-making, specifically about buying and selling. We do this every day, ranging from a double latte with cinnamon for $6 or a nice sculpture for the front...
How do you come up with that really great idea? Group think? Or does it come down to one person’s quest?
What is the nexus between entrepreneurship and creativity? Are they inexorably linked or are they orthogonal? Last I looked, there is no SAT test for measuring either of those characteristics....
If we know the rules, why do we ignore them?
This is potpourri time. Or said another way, tales from the crypt.Recently I took my favorite CEO, Bobby Brannigan of Mercato, to lunch. He has a simple problem. He needs...
How to keep your audience engaged
Do you find people get distracted when you are talking or do you wander when the other guy is talking? In our world of high-speed media bits, bytes and baloney,...
Innovative economy: Buckle up and hang on
CONNECT held its second annual Innovation Day on Sept. 14 at Petco Park where over 3,600 people came to celebrate the past, present and future of our innovation economy, to...
Why do people quit so soon after getting a great promotion?
“Harry, you have done a fabulous job. I am promoting you to assistant VP of worldwide global advisory services, and I am increasing your annual salary by 31 percent.”“Thank you....
Why s need to keep ists honest
s.No, not the wooden ones in your house. I am referring to the ones where big shots sit in a semi-circle on the dais with a and a couple...
When your resume says you’re a member of Mensa what does that mean to an employer?
I get a resume. In it, the guy tells me everything he has done and what he can do for me, and he ends by mentioning that he is a...
Making the pitch: If you have a great story, get a great storyteller
One of the early things that an entrepreneur worries about is raising money and giving The Pitch.There are pitch fests where you get two minutes, there are incubators that teach...
How seemingly good incentives can lead to dumb decisions
Now tell me true, do you love your bank?Banking is not as easy as it used to be. For example, in 2023 alone, let’s consider bank failures by Silicon Valley...
Why a little chaos is a good thing
Chaos can be good for your health. When paired with leverage and small bets, it is a three-course tasting menu for a certain kind of entrepreneur. Namely, one willing to...
How I gambled on the ‘Chipwich’ craze – and lost
It is summer. I scream, you scream, we all scream for ice cream. Last week my neighbor gave me some chocolate chip cookies and mentioned in ing that she used...
Here’s what’s on our summer reading list for entrepreneurs
Summer reading. When I was in high school (1882-1886), each summer there would be a reading list to prepare for the fall. I will refrain from any snarky comments about...
Getting beyond the ‘yes-but’ with clients
How hard is it to get to “yes?”I recently had lunch with a client who is an investment banker, and I ask him how his business is going. He replies,...
Why you should ditch those luxury logos if you’re trying to be a team player
My dad was a radiologist, reasonably successful, highly respected at the university and the hospital, and for his entire life, he wore a simple Timex watch. Metal band, plain face....
Why is it so hard to convince people of the value of cooperation?
I recently got an education in entrepreneurship meets how the world really works.In the classic economic model, the perfect outcome for the rapid growth of a platform is to try...
A conversation with the founders of EvoNexus
My bride, Ms. Barbara Bry, and I recently had a slice of pizza with the two founders of EvoNexus — technology entrepreneur Rory Moore and Walter Davis, who served in...
Do you know when to quit? Some tips from a former pro poker player
Professional poker players know that continuing to play until they win — however they define winning — is often a losing strategy. Expert players abandon about 80 percent of their...
Are you hurting your company by not taking enough risk?
Let’s think about risk and outcomes.Tim Koller and Dan Lovallo, McKinsey executives, recently put out a paper on “Overcoming a Bias Against Risk.” Their theme is that corporations have become...
Did you just negotiate against yourself?
From time to time, I do some “CEO coaching.” I think coaching can be a bit squishy in that it is hard to measure your value. Did your brilliant insight...
In tough times do you cut people or cut salaries?
For those of us who have recently been told by the venture capital community to pound sand, it is time for a little schadenfreude.According to PitchBook, “for the first time...
Why we selectively forget our wrongdoings
A simple story. I will let readers reach their own conclusion.I have subscribed to The New Yorker magazine for more than 30 years. Last week, I got a piece of...
Why rejection is such a powerful motivator
When you have success, it is OK to celebrate. After all, good things showed up and happy outcomes are like hors d’ oeuvres. When they are ing them on that...
A work email that breaks all the rules – and not in a good way. How to tell your own story
Before I begin my weekly offering, allow me to wander back in time. Two weeks ago, my column, which included Adam Grant’s rules for proper email etiquette, generated an unusually...
Why are we so good at making bad decisions?
Free.Turn on the radio, television, Internet, social media or a lunar landing and within a few minutes you will hear the word “free.” Let’s agree that from both a metaphysical...
Can’t tell me what you want out of a deal? That could be a deal breaker
What would you like?Now I want you to think about that question. It is a trick question that I use in all my negotiations because it forces the other side...
Why is it so hard to tell the truth?
Do we no longer value the truth?Entrepreneurs start their adventure with a commitment to “change the world” or at a minimum to make it better. Much has been written about...
Why meeting face-to-face – and we don’t mean on Zoom – still matters in business
I just got back from a conference with real people standing next to me, no avatars, no virtual, no Zoom. We were in person, and I traveled on a nonstop...
Maybe we need to laugh a bit more?
Heard last month in the halls of Silicon Valley Bank.Knock, knockWho’s there?Cannelloni.Cannelloni who?Cannelloni some money ‘til next week?A long time ago, I worked in Hollywood as a sitcom writer, and...
Can executives at a startup be best friends forever? Should they?
BFF — Best Friends Forever. Do you have any, or perhaps, I should ask how many?The idea of a best friend intrigues me, and writer Jaya Saxena, in her article...
Should it be easier for the little guy to get into private deals?
So you want to be an “angel investor.” You already know that anyone can invest in the public markets (stock exchanges, e.g.), but to get in on the really good...
Why you should consider going to that high school reunion
I have a high school reunion coming up in a few months. There is zero chance of my sharing the number, but the question is, should I go? Statistically, about...
Most unicorns were not obvious unicorns when they were funded
As of January, about 639 “startup unicorns” existed in the United States. A unicorn is defined as a company worth at least $1 billion.As of January, there were approximately 33...
Why some corporate leaders continue to invest in losing ventures
Jan. 30, 2 p.m. I have a long-time friend. He is facing the classic rock and a hard place. Fume date is on the near horizon, and it is likely...
After unplanned unemployment, it’s time to take a deep breath
You must be kidding me. Goodnight Irene?Either the current company you founded just went kaput, or you were fired from a larger company run by a maniac (not naming names)...