Mads Singers Management Podcast

Management is ultimately about problem-solving.  Oftentimes those answers aren’t readily apparent because humans are involved, and they are definitely more complex aspects of any problem!

Today’s guest for Mads Singers Management Podcast, Zuzana Dobro, is someone who, like me, likes solving these human problems.  Zuzana helps entrepreneurs think transformationally.  She’s spent over a decade consulting both in house and with agencies on customer and user experience.  She’s worked with startups, Fortune 500 companies, and everything in between.

Early in the episode Zuzana and I talked about relationships.  I noted that there are some people who are particularly talented in SEO but for some reason have absolutely no talent at building relationships.  One of the most important things in management is to build relationships with the people who work for you.  Not only does that make for a more cohesive work environment, it’ll also increase team productivity.

Relationship-building is what Zuzana does when she is working with teams that cannot come to a consensus.  She relishes the chance to brainstorm, facilitate, and use the fact that she’s not a direct stakeholder to bring objectivity and a solution-oriented approach.  I agreed with her and stress with my clients that it’s not about “winning” or “losing” when getting to a consensus for a decision, but finding a solution that presents the best outcome for everyone.

Zuzana asked me about how I screen for clients and I told her one of the very first things I look at is personality, particularly DISC.  If I don’t think I’ll be able to coach someone based on their personality, I won’t take them.  I also put all potential clients through my management course.  The goal here is to try to pre-emptively address some issues so that when we do finally get to coaching, we share a common vocabulary and methodology.  Zuzana noted that when she doesn’t feel comfortable with a potential client she’s very happy to refer that business out and keeps up relationships with colleagues in order to do just that.

Part of keeping up those relationships is keeping your word, and Zuzana talked about how small the business world can be, and how you can’t afford to develop a bad relationship as a management coach: don’t burn bridges as entrepreneurs are always sharing information...as well as the names of good, as well as bad, service providers with each other.

Key Learning Points:

 1. Mads shares a weakness of those who excel in SEO - 6:58

2. Zuzana notes a key trait of good managers - 9:35

3. Mads underlines the importance of setting expectations of communication with clients - 12:35

4. Zuzana reminds us that reputation really does matter - 16:35

5. Mads explains how he screens for clients - 20:35

6. Mads discusses a strategy for shaping decisions prior to a meeting - 25:40

7. Zuzana offers an alternative strategy when there isn’t consensus prior to a meeting - 30:13

8. Mads talks about the difference between outcomes and solutions - 41:10

9. Mads notes how communication has to change when chasing bigger clients - 43:00

Connect with Zuzana Dobro:

 1. Zuzana Dobro

While the Internet has created so many new opportunities for building business and creating revenues, the realities of the traditional business world have not disappeared.  In fact, with legislation like FATCA and GDPR now in place, it’s more important than ever to have access to a legal mind who understands the digital world.

John Di Giacomo, today’s guest for Mads Singers Management Podcast, is precisely one of those legal minds.  John has an internet law firm called Revision Legal which specifically serves those people who make money on the internet.  He’s been in the “internet law” business for a decade now and has plenty of war stories to share.  

One of those stories was about legal trolls: people who find laws that you might be “violating” and then try to make you pay for those “violations.”  One such scam involves the Americans with Disabilities Act (ADA) and website compliance with that act.  These trolls will test a site to see if the website is accessible to those with disabilities and if not, send a demand for compensation or even file a lawsuit.  John shared some tips on how to amend your website terms and conditions to avoid these trolls, but if you want to learn more, there’s plenty more ADA knowledge on his website.

He also noted that the COVID crisis has actually brought a fair amount of buying and selling in digital businesses and that he’s had a fair amount of work during this time.  But that’s also reminded him of things people fail to do when operating their businesses with a future sale in mind.  One of those things is locking down trademarks.  He shared a case in which a company with dozens of restaurants in its portfolio had to go through an expensive and time-consuming renaming process simply because someone else had duly filed a copyright on the name and ordered a cease-and-desist.

He also warns against inexperienced buyers thinking they can just waltz in and operate a business.  John notes, “it’s not enough to have ‘read all the books’ or ‘listened to all the podcasts.’” There is no substitute for experience.

John has also had a fair number of FBA clients, and as such, has had to deal a lot with Amazon on legal matters.  While some of my friends and clients were involved in FBA businesses, some of what John had to share Amazon’s policies and legal stances were really interesting.

John was our first lawyer ever on the podcast and he’s set a great standard for future lawyers to appear.  Enjoy!

Key Learning Points:

1. John shares what kind of activity he’s seen a rise in during the COVID crisis - 2:25

2. John discusses what the true worth of a business is - 6:00

3. John warns about earnouts - 7:45

4. John notes the challenges of working with Amazon - 11:47

5. John talks about dealing with remote employees - 16:53

6. John clarifies that digital assets can be difficult to protect (and value) - 20:12

7. John relates a trolling technique and how we can counteract it - 22:03

8. John gives us a strategy for developing business in the US - 26:53

9. John discusses the costs of getting a trademark - 31:00

Connect with John Di Giacomo:

1. Revision Legal

2. Facebook

3. Twitter

4. LinkedIn

Believe it or not, even when you’ve grown a business to a level that allows you to step away, business owners struggle to do just that.  It’s a good problem to have, but even better, it’s a problem you can deal with if you are willing to make some important changes.

Today’s guest for Mads Singers Management Podcast, Adam Anderson, is someone who has had to make those important changes multiple times.  Adam has spent 22 years as a tech entrepreneur, specifically in the area of cybersecurity.  He’s had almost two dozen companies and they represent wonderful successes, disappointing failures, and one great sale.  That sale made him think he was special, but over time he’s learned that he was lucky, and that process of learning to grow beyond luck has given him what he calls a “Street MBA” in which you learn by doing. 

Adam is particularly proud of the people who have come to work for him who were either young or inexperienced (or both!) and were transformed by working with him.  One particular group of developers started with him from scratch in one particular business and within the space of a few years were making 6-figure incomes.  This reminded me of a couple excellent employees that I’ve had the chance to develop over the years, both of whom were 18 years old with no education when they started with me and now manage 60 people each.  

This influence and authority over your employees is very powerful and Adam shares at least one occasion in which he felt he did not use that power for good.  In trying to encourage a playful and irreverent “anti-corporate” atmosphere, he created such a party environment that an employee got addicted to alcohol and ruined his life.  

That influence needs to be particularly present when promoting staff into management.  Adam made the mistake of thinking that everyone was entrepreneurially-minded (like himself) and hence used the “throw them in the deep end” strategy when he promoted people into management.  He learned the hard way (and pretty quickly) that this was no strategy at all.  I concurred, underlining an important theme in my coaching: people can learn and grow into management skills, but they have to be taught how to do so: they can’t just be expected to “learn it as they go.”

Once you do get those people properly trained you are free to step away from the business, and Andy confessed that he had a hard time doing that.  He had to learn to trust the process and not interfere with his management team, otherwise, they were never going to grow.  He’s learned how to add value to his company as a whole and gives us some great networking tips (I add one of my own!).

Key Learning Points:

1. Adam reflects on the things that make him smile the most - 2:50

2. Mads adds satisfying similarities in his own journey as an employer - 4:35

3. Adam warns about the dangers of promoting great performers into management - 11:00

4. Adam also notes that “abandonment” is not a great strategy for new promotions - 13:00

5. Adam shares his surprise at how challenging it was to manage managers - 15:00

6. Mads assures Adam that he sees this problem all the time - 18:45

7. Adam tells us his new “most important job” once he was removed from day to day operations - 23:50

8. Mads adds a tip for “getting lucky” - 24:30

9. Mads gives some alternative strategies for networking when there don’t seem to be obvious opportunities - 27:50

10. Adam gives us the reason why networking is not prospecting - 28:53

11. Mads shares an organization that is great for networking but isn’t normally thought of as a networking organization - 29:40

12. Adam tells us his four stages of business building - 31:36

13. Mads reminds us that management can indeed be fun - 37:50

Connect with Adam Anderson:

1. Adam Anderson CEO

It’s one thing to manage a team of 2-3 that grows to a team of 5-6.  It’s entirely different to go from managing a team of 10 to a team of 30.  My guest for this episode of Mads Singers Management Podcast, Andy Allaway, is someone who has done precisely that for the juggernaut known as Empire Flippers.  Andy comes originally from a sales background in the IT industry before he made a switch almost four years ago to take on running operations for Empire Flippers.  He runs his worldwide remote team of 30 from the center of Europe, in Prague.

Andy shared that one of the great strengths of Empire Flippers is documenting processes.  This makes onboarding and cross-training (to help the team better understand their counterparts in different departments) much easier.  When I asked what qualities Andy looked for in building out his team, he really stressed cultural fit, which is something I very much advocate for as well.  When you hire someone who is “really great” but who isn’t a cultural fit, it ends up badly for everyone, not just the wrong hire.

Andy also shared the challenges of managing the human capital around seasonality in the business brokering business.  It turns out that there’s a lot of activity in Q1 after people finish a great Q4 and year.  That means he’s had to be smarter and more intentional about where and how he deploys his team so they aren’t just sitting around during quieter times.  His operations staff are divided into:

• Vetting (are these quality businesses worth selling?)
• Customer service (challenges from both buyers and sellers)
• Migration (helping a buyer get rolling in his/her new business)

One of the advantages of growing his team, Andy noted, was that as the team got larger, he was able to build specialists instead of having “everybody do everything.”  And that makes sense, the skill set for vetting -- detail orientation and digging through spreadsheets -- is entirely different from the friendly and calming orientation of those in customer service.

Andy also noted that as his team grew, he wanted to improve as a manager, and he would ask potential employees how they would like to be managed.  I told him that a more helpful reframe might be to ask what their best and worst bosses were like.  They would then not only tell me about their past experiences but also indicate what kind of management style they really preferred.  If you have the opposite type of style, it won’t be a good fit.

Key Learning Points:

1. Andy talks about starting with a team of 10 (that’s currently at 30) - 3:34

2. Mads warns about the dangers of hiring Mini-Mes - 4:45

3. Andy talks about the importance of hiring for cultural fit - 7:07

4. Mads discusses the dangers of just hiring a “body” instead of hiring for cultural fit - 9:40

5. Andy shares a favorite interview question - 12:25

6. Mads offers two variations on that question - 12:51

7. Andy discusses his biggest management challenge in operations - 19:10

8. Andy discusses seasonality within Empire Flippers - 26:20

9. Mads share some tips for how remote teams can be more social with each other - 29:22

10. Mads cautions on “skip level” (below your direct reports) 1-to-1s - 34:00

Resources Mentioned:

Traction by Gino Wickman

Connect with Andy Allaway:

1. Empire Flippers

Behind every successful entrepreneur is some kind of routine.  It doesn’t mean that it has to be a very elaborate one or one that checks off every single box recommended by the gurus.  It just means that you have an anchor that helps guide your day.

My guest for this episode of Mads Singers Management Podcast, Jade Green, is someone who practices what she preaches when it comes to routine.  Jade describes herself as the type of entrepreneur who is usually flying in from Bali, where she may have been running a business accelerator, in high heels, carrying a giant surfboard bag that might have a whiteboard or two inside as well.  She’s a presenter, coach, facilitator, and so much more.  

We got right into it, talking about her notion of an “ideal week.”  She pointed out two positives of a job that we often don’t think about: 

• There’s some basic structure
• You know when the day is done and you can choose to switch off

If business owners don’t have some basic structure and don’t have a system for “turning off” and being done for the day, it can be difficult to get deep work done and get into flow state.  If you don’t know where to start, Jade suggests simply looking at everything that needs to be done this week and next and organizing your days and to-do lists, taking care to batch things with similar energies (i.e. the energy necessary for networking and client calls is quite different from planning and composing emails).  I like to organize my ideal week on Sunday nights.

She was also transparent enough to walk us through not just her morning routine, but here evening routine as well.  I’ve observed this trait in successful entrepreneurs and it’s just another way of drawing appropriate boundaries.  If you can indicate to your mind and body that the day is over, you are giving yourself the gift of switching off, which is a key part of regenerating and coming back to do it all over again the next day.  Some people see being “always on” as a superpower, but Jade advocates for a rhythm that isn’t subordinated to hustle culture.

We also discussed a higher level strategy than the ideal week, which is her “90 Day Plan,” which breaks big projects and goals into 12 weeks.  “You overestimate what you can in a year and underestimate what you can do in three months,” she noted.  By being intentional with your goal setting you can get so much more done in quarterly chunks than you can in annual planning.

I loved Jade’s energy during the episode and I know you will too.  Enjoy!

Key Learning Points:

 1. Jade describes the value of an “ideal week” - 2:06

2. Jade shares just how to get started planning an ideal week - 5:25

3. Jade talks about the importance of matching tasks on your list to the type of energy required - 6:40

4. Mads discusses focusing on strengths - 8:30

5. Jade walks us through her morning routine - 11:51

6. Jade also offers an end-of-day routine - 14:25

7. Mads reveals why he doesn’t watch much TV - 17:58

8. Mads shares his “20% strategy” when it comes to coaching - 21:25

9. Jade explains the “90 Day Plan” - 25:10

10. Jade talks about the importance of “filling your cup” - 31:05

Resources Mentioned:
Own the Day by Aubrey Marcus

Twelve Week Year by Brian P. Moran

Atomic Habits by James Clear 

Connect with Jade Green:

1. Jade Green

2. LinkedIn

3. Instagram

4. Facebook

Some years ago you may have had to convince people that content marketing was useful, or even more importantly, that they might need it for their own businesses.  That’s not the case anymore.  Content truly is king in this era of the internet, and even the search engines have learned how to (mostly) parse the good content from the bad.

In this episode of Mads Singers Management Podcast, I welcome Sofie Couwenbergh of Let Me Write That Down For You, which, as you can guess from the name, is a content creation firm. Sofie has had that business for eight years now.  Before that Sofie was the in-house copywriter for an international publisher.  Not content to write for a living, Sofie also does it in a side business, her travel site Wonderful Wanderings.

In my different businesses, content creation is key and I wanted to hear Sofie’s take on whether this should be an in-house priority or something that is hired out.  She immediately asked:

• How much content do you need?
• Do you need it consistently?

The answer to these questions will indicate whether you are looking at a one-shot project (outsource) or something that you’re going to need consistently (consider a dedicated contractor or a hire).  “Google is always changing, your competitors are always updating their content: if you’re not giving content serious attention, you’re going to be left behind,” Sofie shared.

So what about hiring people and how to find great writers?  Sofie gave some great tips on what to do if you do end up using a large marketplace like Upwork.  But she also shared a little known place where you can find great writers without having to pay Upwork’s fees.  We also agreed that the more you pay, the likelier you are to get “publish-ready” content that doesn’t require a lot of editing.  You can save money by hiring someone cheaper, but you’ll spend that in the time you need to spend getting their work up to par.

Sofie also shared that when you do bring someone in the house, you don’t want to throw everything at them at once.  Document all the steps (hopefully because you have modeled them yourself) via documents or videos, and make sure your hires have everything they need to succeed.  

Sofie’s passion for getting her client’s messages right (she calls herself a “straightforward perfectionist”) is palpable and after listening to this episode you’ll have a better sense of some of what goes on behind the scenes in creating high-quality content and corresponding high rankings in search results.

Key Learning Points:

1. Sofie talks about the choice between doing content in house vs outsourcing it - 2:45

2. Sofie discusses the importance of content - 5:20

3. Sofie shares the challenges of hiring in a large marketplace like Upwork - 7:45

4. Sofie gives us a lesser-known place to find great writers - 8:44

5. Mads discusses the advantage of using someone who consistently writes for a living - 12:49

6. Sofie offers pointers about training someone for in house content - 19:13

Connect with Sofie Couwenbergh:

1. Let Me Write That Down For You

It’s a golden age for podcasts.  They deliver news, drive lead generation and marketing, and feature long-form conversations on every subject under the sun.

Our guest for this episode of Mads Singers Management Podcast is someone who lives and breathes in that podcast world, Harry Morton.  Harry is the founder of Lower Street, a podcast production agency that helps people grow their brands and create great podcasts.  They also help create internal podcasts for large organizations to share policies, information, and culture.

Podcasting is trendy right now and that means people are flocking to work in the industry.  That can lead to “too many applicants,” which is a problem some business owners would like to have, but which was also a great lesson to Harry early on.  He thought that experience in the industry was going to be the key piece of the puzzle for each applicant, but what he found (and what made sense in Lower Street company culture) was that creativity was the secret sauce.  Harry noted that a creative can always learn the industry, but you can’t take someone with industry experience and make him/her creative and flexible.

That’s another part of the culture he’s created with his team at Lower Street: a small team.  A small team working with a particular number of clients, as opposed to an enormous agency working with innumerable clients, has an appeal to just the sort of people that have thrived with him.  These employees tend to be:

• Technically competent
• Caring
• All in on the culture and work ethic of the company

Small has been a strength for him when hiring.

One of the paths of discussion we took when Harry discussed managing creatives (and a topic that often comes up with my management coaching clients) was communication and motivation with members of your team depending on how they think.  Developers, for example, tend to communicate in written form, at length, in great detail.  That means that not only do you have to adapt to getting communication like that from them, you should also mirror that communication back (instead of your preferred method, which may be spoken instead of written).  Developers may also be less money-motivated, but that doesn’t mean they can’t be motivated by things.  If you give them a bigger screen or a more comfortable chair, things that make them more effective, you will see the appreciation and even better performance from them.

I enjoyed learning about how Harry runs his company and I think you will too!

Key Learning Points:

1. Harry discusses the pros and cons of managing creatives - 2:30

2. Mads notes how developers tend to communicate - 3:57

3. Harry talks about the relationship creatives have with deadlines - 7:40

4. Harry shares what he’s discovered about hiring - 9:10

5. Mads compares attitude and mentality to skill set when hiring - 10:35

6. Mads explores the myth of “money motivation” - 12:02

7. Harry explains the “problem” of “too many applicants” - 18:15

8. Harry shares the appeal of a small team to certain applicants - 24:40

Resources Mentioned:

Lower Street

Connect with Harry Morton:

1. Twitter

A lot of people have read Tim Ferriss’ The Four Hour Work Week.  Many of those have gone on to try to live, in some part, the lifestyle of the digital nomad that Tim champions in that book.  Of those, few have persevered beyond their first failures to one or more successes.  That lesson, the lesson of “failing forward,” isn’t really discussed in the book but is a key part of the life of successful digital nomads.

On this episode of Mads Singers Management Podcast I chat with Amar Ghose, who grew up in Silicon Valley and read The Four Hour Work Week  when it first came out.  That planted a seed that led Amar to try establishing several different businesses with varying degrees of success until in 2013 he co-founded Zenmaid, which is a scheduling software for maid services.  He’s got a remote team of 20, distributed around the world, and has himself been living the nomad life since 2015.

One of the things that Amar learned during the lockdowns earlier this year was the value of 1-to-1s.  He had a chance to ask his team what they were interested in learning about and doing during the rest of the year and found out some hidden desires and talents, for example that one of his team wanted to do some copywriting, even though they were in an entirely unrelated department.  This opened up an avenue for me to stress (as I do in my management course) that 1-to-1s are always to be done with regular reports on a weekly basis, not just during a lockdown but even during “normal” times.  

A trait Amar looks for when hiring that I really appreciated was the desire to develop personally and seek feedback (and receive it graciously).  He talked about how far some of his team had come in the years they had been together because of this trait.

We also got to learn a bit about his motivations behind acquiring a SaaS business, Burnchurn.io, that is unrelated to ZenMaid but still benefits from the way Amar has been learning to grow and manage businesses.  One of those ways is the strategy of “managing up,” which Amar looked into more closely when an employee sent him a Harvard Business Review article on the topic.  In brief, this strategy allows Amar to work for his team in different departments, insofar as he often looks over solutions that the team has already come up with.  By more trust and delegation, Amar has been able to apply himself where he is most needed and valuable, and that’s a game-changer for a small business.

Key Learning Points:

1. Amar shares his biggest management challenge - 2:54

2. Amar discusses the importance of 1 on 1 meeting during the lockdown - 8:30

3. Mads stresses the importance of regular 1 on 1s with direct reports - 11:45

4. Amar shares a key trait he looks for when hiring - 13:01

5. Amar shares (for the first time anywhere) his acquisition of burnchurn.io - 14:35

6. Amar notes the challenges of being a non-technical founder - 18:55

7. Amar talks about “managing up” is a game-changer - 22:35

8. Amar discusses his annual MRR goals for ZenMaid - 28:30

9. Amar tries to sell Mads on the value of using Twitter - 35:05

Connect with Amar Ghose:

1. Twitter

One of the most important lessons I consistently preach in my courses and with my private coaching clients is having the right people in the right place for the right reason.  Most of us lack the management skills to make a correction when necessary and end up costing themselves, their teams, and their companies a lot of time.

On this episode of Mads Singers Management Podcast I chat with Stewart about his 20+ years experience in IT and over 30 years experience in sales.  Stewart was at Sun Microsystems and worked on Solaris and Java in those heady days before Sun was acquired by Oracle.  He also joined Zendesk pre-IPO.  With more than a decade in “corporate life” he has an understanding of how big organizations work, as well as a lot of background in persuading others to use the software that he is currently representing, which helps him in his current role, securing indirect partnerships for SaaS businesses.  

One of our points of agreement during this discussion was the importance of trusting your gut as you build your team.  Stewart noted that he doubted his gut feeling about letting someone go, and as a result that mistake compounded for months.  This is something I see all the time, and I try to remind people that being a “good person” is not sufficient to stay employed, both practically and personally.  When people are underperforming, they are unhappy, and the fear of firing such people is a lose/lose for everyone.  Stewart noted that the corporate treatment exemplifies this cowardice in labeling someone as a “special project” and putting them somewhere they can’t mess anything up.

Stewart, like I do, also believes in really niching down.  He notes, “Who is the person I am trying to sell to and what is the value I am willing to bring to them?”  He lives this advice in offering himself as an expert on SaaS, in the B2B format, in Europe.  Specific enough for you?  That said, you also have to be careful about pivoting too much, as you can sometimes lose your existing customers by doing so.

Key Learning Points:

1. Stewart prefers to focus on the extra value/margin to be gained on existing customers rather than worrying about churn - 6:30

2. Mads discusses the importance of niching down in regards to lead gen - 12:30

3. Stewart discusses the velocity of firing (and trusting your gut) - 14:05

4. Stewart warns about those who interview well but aren’t a good fit for the role/team/organization - 18:15

Connect with Stewart Townsend:

1. Stewart Townsend

Change is hard in life in general, but particularly so when you’re moving to a new way of managing your company and executive team.  Some will not buy into the changes and find their way to the exit, others may resist and not actively support the new system.  That’s why it’s so important that the owner believes in the change and reinforces that change in his management team and all the way down to front line staff.

Neel Parekh of MaidThis went through this about a year ago and on this episode of Mads Singers Management Podcast he tells us about how he successfully implemented the Entrepreneurial Operating System (EOS).  Neel shares some tactics that really helped his team to accept the new program and work through some of the awkwardness at the beginning of the implementation process.  Neel and his team have been scaling and growing, and just recently franchised his successful MaidThis brand, which is a cleaning service dedicated to vacation rentals and Airbnbs.  You might also enjoy, as I did, the fact that Neel is constantly turning the tables to ask me questions!  I respect and enjoy his curiosity and I think you’ll find some great content, particularly on how to run better meetings.

While it was awkward for him and his team in the beginning (it felt unnatural), Neel persevered and used scorecards to track KPIs for his direct reports.  I emphasized the importance of personal conversations during 1-to-1 meetings (including the fact that they should happen every week for direct reports).  If you don’t get to know your team, you will have no greater context for what they do and why they do it.

We also talked about team meetings and how different they are from 1-to-1s.  Neel asked how often a manager should be talking in the meeting and I said, “As little as possible.”  I reminded him of my principle: a manager should talk last and least.  If you have difficulty with this, consider designating someone as the meeting manager to keep things on track.

If you insist on talking in team meetings, you will often take away agency from your team.  When you offer a “solution” you take away the oxygen from their journey to find a solution.  When you’ve told them your preference how are they going to come up with their own?  A team has to solve these challenges together, without you, otherwise, they can’t ever grow.

Key Learning Points:

1. Neel describes how his company implemented EOS - 2:47

2. Mads insists on the importance of 1-to-1 meetings - 6:45

3. Mads explains his philosophy regarding team meetings - 9:43

4. Mads notes the importance of a meeting manager - 11:10

5. Mads cautions us on what happens when departments don’t communicate - 16:20

6. Mads chats about DISC - 24:57

7. Neel shares how blue-collar workers respond to recognition and compensation - 29:50

8. Neel discusses ideal candidates for a MaidThis franchise - 33:10

Connect with Neel Parekh:

1. Neel Parekh

2.  MaidThis Franchise