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Tim’s overall message - Dare to look within
Date Published:
Ryan McMillan from Atlas Digital
Ryan McMillan

Read: Tim Duggan - Leadership Lessons for Time Poor Founders

As an entrepreneur himself, and having interviewed dozens of fellow founders while researching his books, it was a privilege to hear firsthand Tim’s lessons on entrepreneurship, creativity, and work. We’ve bundled these lessons together, so you can use them now, or bank them for later.

Date Published:
Ryan McMillan from Atlas Digital
Ryan McMillan

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Tim's books are a treasure trove of wisdom for founders

Lesson 1 - Launch into a rising tide

Success often comes by aligning with movements larger than oneself. Identify and leverage burgeoning trends or sentiments to propel your initiative forward. This strategic positioning can act as a catalyst, accelerating your journey towards achieving a coveted Cult Status.

“There's a concept in Cult Status where one of the seven steps to achieving [Cult Status] is about launching into a rising tide. That is the idea that you need to find something that's bigger than just you if you want it to be successful. Both basically wanted to have a shortcut to success.” 

Lesson 2 - Humanise B2B interactions

Treat B2B engagements with the same principles as B2C. Businesses, at their core, are collections of individual people. Embrace this human element to make meaningful connections, ensuring your strategies resonate on a personal level, regardless of the business context.

“I think sometimes there's an issue that we separate B2B and B2C startups and think of them as though they're these two separate beasts, and they don't have that much in common. Whereas I think B2B and B2C have so much in common, because at the end of the day, the people that make up businesses are consumers. So I think that sometimes we think that businesses are these beasts that don't have much in common with consumers and we need our own rules for them. Whereas every business is made up of dozens, 100s, 1000s of individuals at their core. So I think about things from generally a B2C world because that's where I come from. But if you apply all of those same principles in a B2B world, they're still going to work because businesses are made up of humans.” 

Lesson 3 - Chasing bigger isn’t always better

Growth isn’t solely about scale; it’s about refining and enhancing. Aim for a business that thrives on quality, impacts meaningfully, and fits your lifestyle goals. Define success on your terms, reach it, reassess, and choose whether to expand or sustain contentedly.

“The biggest lesson that I learned as I took a company from startup to scale up was that chasing bigger is not always better. It's sometimes a bit jarring to hear in this world of entrepreneurship, because we are told as founders that your job is to make as much revenue as possible and build as big an audience as possible. And build as big a team as you can. And short for some people and some businesses, that's great, but bigger is not always better.”

“I actually think that some businesses can build phenomenal businesses with a team that gets to a certain size and then it's just all about refining the business model in order to increase the margin or in order to impact more people, or in order to make it a great lifestyle for the people in the business and the founders of the business.” 

“Some of the terminology that we often get used in the scale-up world is all about 10x and 100x, and going bigger and better. And I just think that that all needs a bit of addressing. My advice to entrepreneurs is to figure out what success looks like for you, not for your parents, not for your peer group, not for your competition, success is for you alone. And then once you reach that, you can then stop and reassess and for some people, the answer might be okay, now I want to go to the next level. And for other people, the answer might be I've got here, I'm happy. I'm content with where I'm at.”

Lesson 4 - Centre your customer

Prioritise the customer’s perspective by addressing three key questions: their initial feelings, the transformation you induce, and the ultimate enablement. This exercise ensures the customer’s needs and experiences are the focal point of your business strategies and creative processes.

“If I had to choose just one of the creativity exercises in Killer Thinking, I would choose a really simple exercise that I love to do at the start of every big meeting called Centering the User. The whole point of centering the user is making sure that the customer who we're trying to reach, who we're trying to have an impact with, is at the centre of what we're thinking about.”

Before any critical meeting, off-site, or strategy session, get everyone to share their answers to these three simple questions with the room:

  1. The customer comes to us feeling […]
  2. We make them feel […] 
  3. So that they can [...]

Sharing the results of these three unfinished sentences between a team is a powerful tool for aligning every decision you make, both strategic and tactical.  

“I remember I did some work a few years ago with one of Australia's biggest banks. I remember going into their large boardroom where they would have their monthly meetings with board executives, and all around the walls of the boardroom were photos of customers. Real customers - people in high vis vests. A family. An older couple. And that meant that when they were in a boardroom and they were making these big decisions around their business, anyone at any stage could just point to the people on the wall and say, ‘Are we doing this for them?’ Are we keeping them at the centre of what we're thinking?” 

Lesson 6 - Dive headfirst into new technologies 

Fear of AI and new tech is natural, but avoidance isn’t the answer. Understanding and engaging with innovation is key. Dive in, experiment, and use knowledge to transform apprehension into opportunity for every industry. Be open-minded; it’s essential for adapting to AI’s advancements.

“There can be a tendency when new technologies come along to be scared of them, or to run away from them, or to write them off. And I think AI is probably the biggest example of that. Not in terms of writing it off, because I I think everyone sees the potential, but in terms of being scared and apprehensive about where it's going to go. And that's perfectly natural because for most of us, it is a new technology that will change almost every part of our lives.” 

“But I think the only way to address technology when it is super innovative and has the ability to completely upend entire industries, is to dive headfirst into it. I think the opposite thing to do is put your head in the sand and pretend or hope that it's not gonna affect your industry because it's going to affect every single industry, my industry, your industry, every single person. And the approach therefore, to innovation, I think needs to be open minded. It needs to be, ‘how can I help use this technology?’ What new opportunities are gonna come off the back of this? As opposed to closed minded or protectionism or just pretending it's not gonna happen.”

“When I was researching Work Backwards, I looked at many research studies around the effect that AI was going to have on our entire lives and jobs and saw this rising apprehension in our society around where it's all going to go. And I think the only way that you can deal with fear is through knowledge and information. That doesn't make it any easier, but at least you understand how it works and how you can make it work for you. I think the only approach that we're gonna have is trying to grab hold of it with two hands and experiment with it, use it, figure out how to understand it, and hopefully that can alleviate some of the apprehension that we have around where technology's going to go.”

Lesson 7 - Seek out investors aligned with your values

(and if you don’t know your values, uncover them using Tim’s MAP method)

Discover investors who share your vision beyond profit. Use Tim’s MAP method to define your values, then seek partners who prioritise impact, like BCorps. 

MAP stands for Meaning, Anchors, Priorities. Taking time to write these down in the context of your personal life, work life, and to make sure you're aligned with potential partners, like new hires, channel partners or investors. Write them down on paper, in your notes app, or in an email to yourself. It doesn’t have to be a long winded exercise, it’s more about taking the time to check in with yourself. 

Values-aligned partners exist and are expanding, championing a holistic approach to business success that includes financial, social, and environmental considerations.

“There is a desire for some investors to question the structures that we have built up. So the structures around most businesses are incentivised solely on financial performance. And it really heartens me that things like BCorps, so the rise of businesses that think about their entire impact on the world, rather than just their financial impact to the world, are starting to take hold. It's still a small movement. There's some companies that are doing it better than others. But at least there is a movement there. And there's the rise of impact investing and then there's the rise of a lot of businesses that are thinking outside of just money.”

Tim implores founders looking for investors with a broader set of values to look around and find investors that are better aligned, because they are out there.

Lesson 8 - Make small adjustments that will change your course over a long horizon

Embrace incremental change. Life’s constraints needn’t deter you when you think about change in small, consistent shifts. Each step, no matter how minor, is progress. Remember, monumental transformations often sprout from modest beginnings. Start small, think big, act now.

“The one outtake I want from [Work Backwards], is for anyone reading it or thinking about it or just even hearing about it for the first time, to stop, pause and reflect on where they are in their life.”

“Most of us get on a treadmill and we don't get off that treadmill until we retire. And we're running as fast as we can. And we're not thinking and we sometimes get caught up in the whirlwind of work and life and everything else that happens around it.”

“So I think the first thing to do is acknowledge that the best time to sort out your MAP is today. And that doesn't mean that you need to throw everything out and reconsider it and stop working. That's not the point of this. The point of this is just understanding where you want to get to.”

“I am a realist, and acknowledge that often, this can be an idealised version of where and how you want to live. And that's not possible for many people right now. You might have a startup that is going through a scale-up phase, you might have a young family, you might be a carer dealing with something terrible in your life, you might have health issues that stop you doing that. There's so many different reasons that are going to stop you from getting to where you want to get to.” 

“However, I think the most important thing is just knowing where you want to get to, because then you can make a small tiny change in your life to get you there, that can be one inch closer than you were yesterday. And that is all that matters.”

“I think it's about clawing back, just some time to yourself, some energy to yourself, some focus on the right things instead of the wrong things, and every minute that you can claw back is a win. So I think sometimes it's easy to get caught up in thinking about “I'm not gonna think about this because it's gonna be too revolutionary for my life.” Whereas I think the most revolutionary things can happen in really small spaces, and that is a win for everyone.” 

Tim’s overall message - Dare to look within

Tim is a treasure trove of wisdom for founders navigating the tumult of entrepreneurship. His approach, distilled from personal experience, and extensive research, underscores the importance of clarity in vision, strategic alignment with larger movements, and the humanisation of business interactions. 

His key takeaway? Have the courage to turn inward and align your deepest motivations with your entrepreneurial journey. Spot a disconnect? Tweak your course in a small but meaningful way.

Tim’s experience is evident that the journey of entrepreneurship is not just about reaching a destination but also about the transformation one undergoes. It’s a path of continuous learning, adapting, and evolving, where the true measure of success lies in the depth of the impact made and the lives touched along the way.  

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