🍼 Why you need a deal doula, meetings are toxic for productivity AND profitability, ...

I listen to 10 hours of podcasts a week, so you don’t have to.

This is the 28th edition of Best 3 Podcasts of the Week 🥉🥈🥇, featuring Lenny’s Podcast, The Rework Podcast, and My First Million

What you need to know

• 📉How to maintain morale during a downturn

• ☢️ Meetings are toxic for productivity AND profitability

• 🍼 Why you need a deal doula

+ BONUS thought 

• 🚶‍♀️ Walking and talking mitigates the downsides of meetings

📉How to maintain morale during a downturn

🥉 Third place (3 min read vs 1 hour 10 mins listening)

The price of bitcoin is like traversing the Himalayas. The descent can cause fatigue, headache, and sickness. One wrong misstep can be fatal. So, how do people remain motivated and upbeat when they’re constantly staring death in the face?

Just looking at this chart makes me queasy. Fortunately, Jason Shah has an antidote. As a web3 Product Manager, he shares how you can maintain morale - for yourself and others - even as the crypto winter gets colder and markets continue to tumble. 

What they say

Progress is everything

In crypto, there are cycles. Morale and the ability to keep building are the determinants of long term success.

The only way to maintain morale is to make progress. No speech, no extrinsic motivator really works. People get really excited when they see progress.

Pretty much every crypto conference has a hackathon and so it keeps the spirit of building alive.

We saw this with AirBnb when the business had a drawdown in revenue. They didn’t know when it was going to turn around. I think what worked was making progress.

Ultimately, if you hire the right people who are motivated for the right reasons, that recipe keeps people highly effective at building for when things do eventually turn around.

Jason Shah

What I say

Why it matters: Only a rare breed of people have what it takes to thrive in a startup. Even less have the ability to stay the course. Those who do understand the power of momentum.

You don’t have to run through a brick wall every day to succeed. Honestly, you can’t. Your body (and mind) give up. That’s why you should sprinkle quick wins between meaty projects. This gives you a spike of dopamine and the energy to go again.

If you want to go deeper on the importance of quick wins, listen to this episode of The Rework Podcast.

Between the lines: You may have noticed less product updates on thepodup.com over the last few months. That’s because I’ve been focusing on quick wins. There was a period where I worked every night, 7 days a week, to get the site live. Burnout was on the horizon.

Once the site launched, I prioritized a number of small projects and growth experiments. They gave me the time to recharge, keep my head up, and focus on the long game. I’m gearing up for another meaty project. Watch this space.

☢️ Meetings are toxic for productivity AND profitability

🥈 Second place (4 min read vs 27 mins listening)

I hear you. This topic has been covered countless times before. Please, bear with me. DHH and Jason Fried shared a lot of polarizing views about meetings on The Rework Podcast. They’re super useful, but take them with a grain of salt. I share a few counter arguments to reframe how you think about the purpose of meetings.

What they say

The true cost of meetings

A 1 hour meeting with 5 people is not 1 hour. It’s 5 hours. And that’s expensive.

You’ve got to think about is it worth spending 5 work hours on this thing that we could probably write up or that 2 people could discuss in 15 minutes.

In most organisations, a meeting is the first default response. But, they should probably be the last thing. You should try to figure out how to communicate without having meetings.

Jason Fried

Meetings destroy deep work

Another key issue is that meetings are synchronous. That is a very expensive way of coordinating things and is a nightmare of juggling calendars.

We’re really big on this notion of long stretches of uninterrupted time. It’s quite difficult to have those long stretches if your day is punctured by meetings.

Sometimes, it’s even worse if those meetings are an hour or so. You’re like ‘I have an hour meeting in the morning and an hour meeting in the afternoon. That’s just 2 hours out of 8 hours. What’s the big deal?

The big deal is that creative endeavours in general don’t yield well to those kinds of interruptions. If you’re 45 minutes out from a meeting, there’s a good chance you’ll look at that time as ‘I’m not going to dive into a big hairy problem. I’m just going to dive into my emails or something else that isn’t really going to move the ball forward.’

David Heinemeier Hansson

What I say

Why it matters: I agree with all of the above, to a point. Meetings can be helpful when viewed through the lens of morale and retention. We humans are social creatures. If individual contributors are locked out of talking to colleagues in the name of productivity, they’ll likely leave and be colleagues no longer.

How do we do it at Medicspot? Teams often have two 30 minute stand ups every week. One on Monday, one on Thursday. We could 100% go without these meetings and be fully asynchronous. But it’s important to have face time with colleagues, to build rapport and trust, and to feel human.

Between the lines: I’ve had two people hand in their notice this year because they want to work in an office environment 4-5 days a week. We do 1-2 days a week. Remote work is fantastic for some - particularly parents like myself - but it may not be rainbows and butterflies for others. 

Young people who want to socialise often prefer to be in the office. They like to learn what’s going on and meet new people during meetings. Don’t be fooled into thinking meetings are all bad. It depends on what the purpose of the meeting is for.

BONUS thought

🚶‍♀️ Walking and talking mitigates the downsides of meetings

There’s something really nice to me about moving and talking. I like to walk and talk. I hate sitting still and talking. I can’t think as clearly.

What’s nice about the phone is you can go on a walk and talk. You can’t do it on camera. I mean you could hold it in front of you but that’s totally weird.

There’s a real advantage to moving your body and thinking. The more you’re on camera, the more stationary you are, which is also really uncomfortable.

Jason Fried

Everyone at Medicspot knows I’m a stickler for a walking meeting. It naturally brings a lot of health benefits, but it also counters the negative aspects of a meeting:

• By default, a phone call has historically been 1:1. This encourages organizers to reduce the number of people on a call.

• You still get the social interaction from talking to another human being. You actually focus more on the conversation rather than checking your appearance on Zoom.

• Walking boosts your mental and physical health, improves clarity of thought, and ultimately, productivity.

🍼 Why you need a deal doula

🥇 First place (3 min read vs 1 hour 2 mins listening)

This isn’t relevant for 99.9% of readers. Until it is. This segment is all about fundraising and M&A. This is a fabulous read that will change how you go about fundraising in the future.

What they say

Problem: a lack of reps

Most people who become business owners and CEOs, you’re great at product, you may be great at marketing or finance, but what you’re not good at is stuff you do once in a while, like fundraising and M&A.

These are large, one-off transactions that are very important and expensive.

You don’t want to get them wrong, but you also don’t have reps in doing it.

The other side, like the investor, they talk to hundreds of people like you every month. They’re getting tons of reps so it’s a very asymmetric skill set.

You don’t know how to negotiate like them. You don’t know what clauses are standard and what are not standard. The same thing goes for M&A.

Shaan Puri

Solution: a deal doula

Is my lawyer great? How am I supposed to assess this? By the time you figure out if your lawyer was good or not in a transaction, it’s too late. It’s done.

Fundraising and M&A is like an intense sprint. It’s this couple of months process that you work on really hard. It becomes your main focus and you’re trying to get to this amazing end point.

The comparison is like you’re birthing a baby. Just like when you’re having a baby, you might have a doula.

A doula is someone who’s there to coach you and guide you. They’ve seen the birth of hundreds of babies whereas this might be your first.

If you’re going to do a deal or fundraising, you need a deal doula. It’s different than a mentor who’s a general thing in life. A deal doula is specific.

Shaan Puri

Advice from Shaan’s doula

Every timeline you think of is wrong. Everything they say is going to fall through. If you’re going to have a normal M&A process, you should expect these bumps and bruises.

You need to turn your company into a giant buy button like when you go to Amazon and it’s one click checkout. You need your data room so organised and precise, ready to answer all of their questions.

You think because these guys are giving you a term sheet that you’re at the end. This is when you’re going to have to sprint the hardest.

Shaan Puri

What I say

Why it matters: Founders receive lots of advice on how to fundraise. What’s missing is the brutal assessment that they’re walking into the lions den. Investors will leverage asymmetric information as much as possible.

Be honest with yourself when your counter party has an advantage. Only then can you find a way to bridge the gap. Shaan’s Deal Doula seems to be the best way to do this, second only to working as a VC or banker yourself.

Between the lines: Shaan Puri loves naming things. Giving something a name can make a concept more credible and memorable. Deal Doula is a great example. Instead of ‘you need an expert who can advise you throughout the sale of your business’, Shaan says you need a Deal Doula. It’s simple, it’s short, and it has alliteration. When you next need to communicate a complex concept, try giving it a name.

Shoutouts

When I find newsletters, podcasts, or books worth sharing, I’ll feature them here:

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Note, these quotes were pulled at different points of the episode. Some sentences were left out to make the narrative clearer and more concise. Podup is not associated or affiliated with any podcast (unless otherwise stated). All roundups are independently written and do not imply any sponsorship or endorsement by the podcast.