I’ve now done 400 episodes of The Less Doing Podcast.
It’s been downloaded 1 million times.
So, it was pretty freakin’ hard to come up with my top five favorites. But I did it and here they are. In no particular order. Links to the original podcast are included.
The Importance of Strategic Coaching for Entrepreneurial Success — A Conversation with Dan Sullivan
Raise your hand if you’re an entrepreneur and you can’t focus.
Here’s the thing: the majority of us are finding ourselves in situations where we have so much going on, but we’re losing our footing.
From meetings to product development, we’ve got to be everywhere. We have to do everything.
No, if you’re asking Dan Sullivan, one of the most experienced business coaches.
With over 35 years of experience, Dan is focused on one thing only: stopping the overworked entrepreneur syndrome.
How Strategic Coaching Helps
Let’s be real: entrepreneurs don’t really need help with management. A tool can help with that.
What entrepreneurs really need is strategic coaching.
We need to get our priorities straight. We need to know what to focus on.
However, we’re surrounded by the buzz.
You know what I’m talking about; all those articles telling you what your next direction should be, team members with their input, your family.
Everyone has something to say.
And you have to stay sane and show up for your business.
It’s easier said than done, which is exactly why strategic coaching helps.
Entrepreneurs have great ideas and skills, plenty of healthy ambition. But they can’t quite focus — there is too much going on. A strategic coach is there to simplify things and help entrepreneurs define their priorities.
If you’re not in a place to get a strategic coach, you can learn from their strategies. Dan was kind enough to share a few lessons:
Strategic Lesson №1: Positive Focus Matters
Whenever you’re meeting with two or more people, start with a positive focus.
Spend two to three minutes talking about things you’re excited about.
This can be previous achievements, future plans — something that can hype everyone. It doesn’t even have to be related to work, as long as it gives everyone in the room a bolt of energy.
Then, start the meeting.
When you’re done, go back to positive focus.
Cheer on everyone for how well they’ve handled the issues you’ve discussed.
According to Dan, positive focus is incredibly important for morning meetings.
Everyone’s coming from different things in their lives, and half of their attention is still focused on them.
By starting off the meeting with positive things, you’ll help everyone reach the same page.
The biggest skill in life is to be where you really are.
Positive focus ensures you and your team are present in the moment.
Strategic Lesson №2: You Have to Neutralize the Critic
Strategic coaches don’t have to be hard on entrepreneurs. No one can be harder on them than they are.
Think about it; chances are, you’re probably the worst boss you’ve ever had.
Dan wants to change that, as well.
Strategic coaching is the art of asking the right questions, not providing the right answers.
In strategic coaching, no one’s going to give you the formula for success. However, coaches will help you pose the right questions.
The crucial thing is to be clear about the area you’re actually good at.
When you, as an entrepreneur, know what your strengths and your weaknesses are, you won’t be exposed to your inner critic as much.
Instead, you’ll focus on doing the work that only you can do.
You’ll have no problem delegating the rest of the work to the people on your team who are more skilled.
Or, as Dan puts it…
Do what you are really, really great at. Everybody else’s job is to free you up in some way.
If you’re an entrepreneur, you know it’s hard to let go and delegate. You feel an immense sense of responsibility.
But if you shift your perspective, you’ll have a lot more time for the things that truly matter.
Strategic Lesson №3: Entrepreneurs Need Rest
Entrepreneurs often wear their burnout syndromes like badges of pride.
Dan Sullivan, who has been a strategic coach for over 30 years, has a problem with that.
You need more free time so you’re operating strategically, not tactically.
A lot of entrepreneurs are perpetually stuck in survival mode.
They’re working so hard that they don’t have an hour of quality free time. This leads to quite literally being unable to think.
You’re adding 25 important things to think about to your plate, and you’re fighting to make it through the day.
And then, Dan says, he asks his clients to take two weeks away and there’s a change:
Two weeks away, and you no longer think about twenty-five different things. You’ve got 3 things on your plate at most, and they’re all strategic.
And the more rest you take, the more will you be able to identify the truly important things.
As an entrepreneur, taking time away isn’t easy, but it’s necessary.
Do it, and you’ll become your own strategic coach.
Do You Know How To Sleep Well? — A Conversation with Dr. Michael Breus
I know what you’re thinking: what kind of question is that?
Do you know how to sleep well?
Ari, we were born with the ability to sleep. It ain’t a skill you can pick up!
Well, it turns out, your sleep quality can be poor, and it’s interfering with the way you think, work, and live.
How to Get Better Sleep: Crash Course
You’re an entrepreneur, you’re in a rush and you needed answers yesterday — I get it.
That’s why I’ve talked to Dr. Michael Breus, AKA the Sleep Doctor.
If we’ve hacked productivity, then Dr. Breus certainly hacked sleep.
An activity we don’t think of as an activity, sleep is crucial to thinking and operating productively. And the right answer to getting more rest isn’t just popping a melatonin pill and calling it a day.
Instead, here’s what you have to know to get better rest tonight:
1. Melatonin won’t help
The first problem with melatonin is the dosage.
Because of a royalty/patent feud, the majority of companies are selling too much melatonin. A single pill doesn’t contain the perfect amount (1/3–1 mg).
It contains a lot more than you need.
And whenever you introduce an exotic hormone to your body, it’s going to impair your body’s natural ability to produce the hormone it needs.
Melatonin isn’t a sleeping pill. It’s a regulator.
It can help your body realign circadian rhythms, but it’s not going to knock you out and push you into the REM phase.
Melatonin is only really useful if you’re naturally a night owl who needs to realign their circadian rhythm.
Otherwise, there are much better methods of improving the sleep you’re getting.
2. Mattress matters
With companies like Casper popping up to promise you better sleep if you invest in a mattress (for possibly the first time in your life), I couldn’t wait to talk about mattresses with dr. Breus.
The main benefit of mattresses is the support they’re giving you.
When I was twenty, I could fall asleep on literally any flat surface. Heck, I could curl into a bus seat and get my daily dose of energy.
But as you grow older, you start needing specific support.
When you’re thinking about purchasing a mattress, don’t think about the price point. Think about the support.
If you have torn discs, get memory foam mattresses that stop you from twisting in the night. Similarly, if you have shoulder or lower back issues, get mattresses that provide specific support for that.
A $10,000 mattress doesn’t have to be more effective than a $500 one. There’s no data to back that up.
Understand the position you sleep in.
If you sleep on your stomach, avoid soft mattresses. They’ll push your lower back in a way that could damage it.
3. Pillow Talk
Similarly to mattresses, your pillows matter because of your sleep position.
If your pillow is too full, it can squish your nose forward, giving you respiratory issues.
The ideal is to have your nose in line with your sternum as you sleep.
If you sleep on your side and you need extra space between your head and your shoulder, you should factor that into your pillow decision.
The goal is to get all the support your body needs for a good night’s sleep.
In fact, the majority of head, neck and shoulder problems come from the wrong pillow.
Dr. Braus advocates buying a new pillow every 18 months since the material quality degrades over time.
You ultimately end up with a pillow that’s not the pillow you bought, or the pillow that can support you.
(Talk about metaphors, huh?)
4. The Perfect Position
Sleeping on your back is actually the perfect sleeping position, even if 70% of people sleep on their side.
When you lie back, all of your weight is evenly distributed. Your limbs aren’t going numb, you’re not crushing your capillaries or moving around during the night. And yet, why can’t we sleep on our backs?
It’s actually a spinal thing.
As we use our bodies throughout the day, we wear down our spinal discs.
When we sleep, they’re rehydrated and grow apart, making us effectively taller when we wake up.
The easiest way to help them rehydrate is by sleeping in a fetal position.
A good way around it is by putting a pillow underneath your knees.
This way, you’re removing the pressure off your pelvis and allowing the discs to recuperate even as you’re sleeping on your back.
5. Banana tea
Finally, dr. Braus recommends brewing a banana tea to get some shuteye:
- Get an organically grown banana
- Leave the peel on and wash it
- Cut off the tips
- Cut the banana (with the peel on) in half
- Put the banana in 3–4 cups of boiling water
- Wait a few minutes
- Presto! You’ve got your banana tea!
Bananas have a lot more magnesium than any other fruit.
And, it turns out, magnesium works wonders for getting you the rest you need to keep doing amazing things!
Phil McKernan — Dealing with Emotions as an Entrepreneur
We talk about skills. We talk about goals and meeting targets. Heck, sometimes when we’re feeling really wild, we talk about doing more by doing less.
But entrepreneurs talk about their emotions the least.
That’s why my conversation with Phil McKernan, a speaker and a coach who brings clarity to entrepreneurs struggling to go forward, brought me so much joy.
It turns out, we don’t just need strategy.
We need emotional clarity in order to make the best decisions for our businesses.
In addition to strategical alignment, you as an entrepreneur need emotional alignment.
If you want to become a brilliant entrepreneur, you can’t avoid raw conversations.
Phil has worked with so many entrepreneurs who thought they needed business coaches who could tell them how to make the most out of their businesses.
It turned out, they were facing obstacles in other areas of their lives.
Their struggles with being better parents or spouses were translating into their business struggles. One area you’re struggling with has the ability to turn everything into one long road overflowing with obstacles.
One client told Phil that the timing wasn’t right to sell their business. Another told him there weren’t any right buyers to sell their business to.
He called bullshit and personally, I think we should be calling our own bullshit a little more often.
What we truly are is scared shitless.
Again, this is normal. This is what it means to be an entrepreneur.
We’re facing the unknown constantly, but we’ve managed to let ourselves define our journeys by the things we’ve accomplished in business.
It’s completely obscuring our view.
Our perception is giving us brain fog.
And our goal is to cut through it.
You Are Replaceable (but that’s good!)
Phil and I agree on one thing: we’re replaceable.
A lot of people — especially entrepreneurs — don’t allow themselves to consider the fact that maybe, just maybe, the world would go on without them.
You hold on tight to your business because there’s nothing else that fulfills you and gives you the meaning you need.
In the long term, it turns you into a person who has trouble letting go of what no longer serves you or helps you grow.
If you have depth in other areas of your life, you won’t be putting all of your meaning-eggs in one basket.
You’ll be fine even if you are the replaceable founder.
Otherwise, you won’t be in emotional alignment.
You’ll reach the top, achieve all you’ve set out to achieve, but you won’t get the sense of satisfaction you’ve been craving all along.
Now, the majority of entrepreneurs face that obstacle and they don’t think about it.
All they do is push themselves into more work.
It’s not a good coping strategy, so Phil goes beyond that when he works with his clients.
Accessing Your Truth
Ultimately, as an entrepreneur who wants to feel happy about their success, you have to understand your emotions and your truth.
So many people have built empires out of a simple need to avoid poverty. They grew up in poverty and they knew they didn’t want to go back there.
However, the pendulum swings the other way around, and it’s another extreme stopping you from accessing your truth.
Once you do examine your emotions and understand what truly drives you to succeed, you will be able to create a life that gives you meaning.
You won’t postpone difficult conversations or add more tasks to your to-do list.
When you’re in emotional alignment, you’ll accept all of who you are. The good, the bad, the ugly. And when you talk about it, you’ll make someone in your audience go: “Holy shit, I am not alone in this.”
Building a Relationship with Yourself
According to Phil (and this is something I can vouch for too), there are three most important relationships that can bring you meaning and help you live in alignment with your truth:
- Your relationship with yourself
- Your relationship with your loved ones
- Your relationship with the work you do
Your relationship with yourself gives you confidence and self-esteem.
Your relationship with the people you love allows you to come home at the end of the day and say: “You know what? I love what I have. I love my family.”
And your relationship with the work you do ultimately helps you do meaningful things and have an impact on your community.
It helps you perceive your work as a true extension of yourself.
Not just something you spend time on to feel as though you’re worthy.
Over time, you’ll see how these relationships compound to help you live a more meaningful life.
Forget about being irreplaceable.
Forget about overworking yourself and experiencing burnout every damn week.
Instead, go out there and find your meaning.
It will tell you everything you need to know.
Jordan Belfort — Sales Lessons from the Original Wolf of Wall Street
You can say whatever you want about Jordan Belfort, but you can’t deny the man knows how to sell.
A natural-born salesman, Jordan Belfort has had his ups and downs, but he’s back and wiser than ever.
In my recent conversation with him, we’ve discussed his ethical persuasion sales system, and how entrepreneurs like us can use it.
Sales Are Natural
Most people fear sales, but they’re everything in life and business.
Sales happens everywhere.
If you’re a parent and you want to convince your kid to do their homework before bed, you’ve got to sell them on the idea.
If you want to share your ideas with the world, you need to sell them to everyone.
Teachers sell constantly; how else are you going to convince your students that learning about ancient emperors is applicable to modern-day situations?
One of the biggest mistakes entrepreneurs make is that they think about sales only in terms of closing deals.
Sales are a process of empowering people with the information you’re giving them.
Closed deals come naturally. You first have to convince them.
For Jordan Belfort, that’s a skill he naturally has.
But for the rest of us, he has a few lessons to share…
1. Persuasion is a linchpin skill
If you want to sell effectively and close deals quicker, you need to become more persuasive.
You can have the world’s best pitch, but unless you’re addressing customers’ objections and selling them on your idea before you sell them on the price, you’re not going to be able to close deals quickly and effectively.
Additionally, persuasion goes further than closing a single deal.
Persuasion helps you turn your customers into raving fans who will go out there and sell your products for you.
In the current situation, getting leads is expensive.
Your marketing program could be costing you so much per every customer you acquire that you may be barely breaking even.
The best way to get new customers and retain your revenue is by getting evangelists on board.
And you can’t do that without being persuasive.
Jordan advocates the oldest trick in the book, which he claims still works: giving away free samples.
You can offer bits of your wisdom through blog posts, or literally offer free samples of your products like they do in grocery stores.
There’s a reason why they’re so persuasive and translate to more sales.
2. “I have to ask my spouse”
One of the objections I hear often is definitely “I have to ask my husband/wife.”
According to Jordan, this is only a valid argument if your prospect is making a significant investment like buying a house.
Everything else is only a way to say: “I’m not convinced by what you’re telling me.”
There are a few ways to overcome those objections and turn your product into the best thing since sliced bread for your customers:
- Don’t address leads’ objections. Instead, deflect them and loop back around to benefits.
- If you’re asking your prospect to make a decision that requires other stakeholders’ input, make sure they’re present at your meeting.
- The key is to make yourself a trustworthy salesperson. Speak about your experience, and relate to your prospect on a human level. For example, Belfort mentions one situation related to the “I need to ask my wife” objection. He approached his prospect by saying: “Of course, John, but I’ve been in this business for a long time, and I can guarantee she doesn’t ask you every time she wants to buy a pair of shoes.”
- Make your company and your product trustworthy. Ideally, the prospect will have already reviewed testimonials from people just like them.
Finally, bring back the conversation to the prospect. Ask them: “Well John, does the idea make sense to you?”
Deflect the objection. Then, go back and emphasize the benefits again. Convince the prospect of what you’re telling them.
You’ll see the objection smokescreen melt before your very eyes.
3. Forget your goals, and focus on your vision
Finally, Jordan has advice for entrepreneurs that’s not strictly related to sales, but it can help you understand your life’s work and your products better.
We’re all obsessed with our goals and getting there.
Jordan says: Transcend your goal setting and focus on your vision.
You have to create a detailed vision of your life.
Imagine where you want to be in five years personally, and imagine where you want your business to be in five years.
Then, understand your vision.
Know why you want your life to look like that.
It’ll help you understand your values and your motivations.
Ultimately, knowing why you’re doing what you’re doing will help you not only believe in your products so you can be more persuasive, but you’ll also overcome obstacles with ease.
After that, the actual selling becomes a piece of cake.
Peter Shallard — How to Be the Entrepreneur You Want to Be
For the majority of entrepreneurs, there is a huge gap between what you should be doing and the kind of entrepreneur you want to be, and the kind of entrepreneur you actually are.
We all have different images of ourselves in our heads.
But come Monday, we open up our laptops and we’re no longer the people we want to be.
So how do we change that?
How do we become the entrepreneurs we’ve always dreamt of being?
According to Peter Shallard, the shrink for entrepreneurs, accountability is key.
How Accountability Improves Your Efficiency
The one thing that Shallard brings into his Commit Action program are principles taken from therapy.
One thing that works with good and bad therapy alike is accountability.
A lot of entrepreneurs today are operating in a vacuum of isolation.
No one knows what they’re doing, no one knows that they’re showing up, day in and day out.
And more importantly: no one is celebrating their success.
Because no one knows what’s happening.
That’s one of the guiding principles behind Commit Action, where entrepreneurs get a coach who can help them feel accountable and positive about the actions they’re taking.
Shallard and his team, including psychology professors from NYU, actually conducted research to back that approach.
It turns out, entrepreneurs who were consistently successful had one thing others did not: people who held them accountable.
And despite all the technology that makes it easier than ever to start and run a profitable company, it’s actually depriving us of the positive psychological environment in which human beings thrive.
Everybody Wants to Hang out with the World
We can blame our ape ancestors for needing environments from which we get recognition and acceptance.
The part of our brain that needs social acceptance and appreciation directly influences our ability to focus.
Being entrepreneurs in our PJs isn’t working for us. We’re lonelier than ever.
The more and more time passes, the less can we focus.
It ultimately creates a state that Shallard calls mental-like schizophrenia. His clients describe feeling like they live with mental sock puppets.
At one point, the puppets cheer them on to stay hyped and efficient. Then the puppets turn on them, criticizing them for not doing enough.
And despite the events and talks that are supposed to make you feel on top of the world and push you into hyper productivity, that’s impossible to maintain without a mental game plan.
It Takes a Village to Organize a Human Brain
We need socialization, and it’s striking that a lot of businesses in the US are actually one-person companies.
Yes, you may outsource your work to freelancers, but if you’re the only one responsible for your activities and your success, and you don’t have anyone to turn to at the end of the day for accountability and recognition, it’ll get lonely soon.
And when it gets lonely, your ability to focus suffers.
Some of the most successful entrepreneurs have entire support nets; teams, boards of directors, coaches, and mentors.
Celebrating wins stops being a monologue, and turns into an accountability dialogue.
It’s why Commit Action works so well.
Shallard offers the minimum viable dose of accountability, perfect for busy entrepreneurs. You just get on the phone with your coach and tell them what you did.
It’s a small step for you, but an immense one for your future.
It’s Okay Not to Be a Powerhouse
Shallard does a lot of work with burnt out entrepreneurs who are at the point where even performing a simple task like making 10 cold calls is too much.
So what does he recommend doing in that kind of situation?
Break down the task.
Is 10 cold calls too much? Make it five.
Is 5 too much? Make a list of people you’re going to call.
Is making a list too much? Dial the first digit.
It’s something, and when you have someone holding you accountable for completing these small goals, it’ll start off a positive reinforcement chain.
In the long term, you’ll be able to commit to greater and greater actions.
Even if the initial actions you’re committing to are barely moving the needle, they’ll compound.
The Key: Implementation Granularity
So, how do you become the entrepreneur you want to be?
By taking action, consistently, and having a healthy environment to do it in.
If your goals are overwhelming you (and you know how the saying goes — if your dreams don’t scare you, they’re not big enough), there’s a simple trick you can use:
Break down the big goal into small tasks.
Climbing Mount Everest is a huge, hairy goal to swallow.
But if you visualize it as taking thirty thousand steps, it’ll become much more achievable.
And if you also have someone to hold you accountable all the while, you’ll improve your productivity and your head game.