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Episode #237
Jack Milroy

How To Turn Custom Consulting Work Into Clear-Cut Offerings

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When you start your consulting business, you want to have clear-cut offerings for potential clients. This eliminates a lot of guesswork and makes things clear on both sides, making for a better business relationship. In this episode, Michael Zipursky talks about custom consultancy and clarity in your offerings with Jack Milroy. A veteran of the political and advocacy scene, Jack shifted to consulting while applying the lessons he learned along the way. Jack talks about pricing models, creating your offerings, and learning to say no. Tune in for more great tips from top consultants while you build your business for success.


I’m very excited to have Jack Milroy joining us. Jack, welcome.

Michael, it’s great to be here. Thanks.

I’m thrilled. I don’t say that very often but I’ve always enjoyed our conversations and seeing how your business has evolved and grown over the years. For those who aren’t familiar with his work and to quickly fill everyone in, Jack is the Managing Director of Defiance where they work with movements, helping them to raise money and build power online. More specifically, they work with unions, political parties and advocacy organizations to level up their digital fundraising and activate their supporters.

Some of their clients include the United Workers Union, the New Democratic Party of BC also known as NDP, the International Association of Firefighters,, as well as many more. You’ve worked as a strategist, leading progressive organizations around the world. I’m excited to dive into this conversation, Jack. We’re going to cover a lot.

Before we get into all the consulting, business building, positioning, pricing and everything that people are here for, let’s start with the history. Take me back to the early chapters of Jack Milroy. Where did you grow up? What was that environment like? What were you doing before you got into the business that you’re in?

I’m Australian. I grew up in Newcastle, Australia, which is about two hours North of Sydney. It’s a mid-sized industrial city. It’s a great place to live with great beaches. I went to university there and got my Law degree. From there, I didn’t ever practice law. I went straight into working on campaigns and unions. Throughout my life, I’ve lived between Australia and where you are, Michael, in Vancouver, Canada. I’ve gone back and forth between the two over the years.

I did not know that you have a Law degree and you ever entertained being a lawyer. This is new information for me. Do you remember why you decided to go away from the path of law?

I knew about halfway through the degree that it wasn’t something I wanted to practice day-to-day. With the day-to-day practice of law, some people love that but it didn’t feel like it was for me. I finished it off because I wanted to finish the degree. It’s a good thing to have. I still draw on it but it wasn’t something I wanted to do every day. I was more interested in working on campaigns and advocacy efforts. I did some government relations stuff early on. The Law degree was helpful. The day-to-day legal practice wasn’t something for me, even though a lot of my friends do that. I ask them questions constantly and get that free help.

Where does the interest in politics and fundraising advocacy come from?

I’ve been interested in politics since I was an early teenager. I ran for everything I could in school. In university, I was involved in student politics and stuff like that. One of my first jobs after I finished high school was working for my local member of parliament in her office. That gave me a good insight into how laws are made, how parliament works and how politics works.

Politics is ultimately what determines the society that we live in. Click To Tweet

I’ve been involved in that stuff for quite a long time and it stuck with me. It’s something I care deeply about and am passionate about. It will always be part of my life. I’m grateful that I’ve been able to build a business around that that keeps me working in that field while also being my boss and building my thing at the same time.

The area of politics is interesting. Many consultants, especially when they’re running either a solo consultancy or a small firm, don’t necessarily feel that politics impacts them. Aside from having your taxes raised, which is something that inevitably seems to happen to everybody, how do you feel politics impacts business?

Another way to position my question would be, in your years of being exposed to politics and advocacy in this general area of work, is there anything that you’ve learned from that or seen in terms of how people hold power or rally a movement around them that you feel applies to the solo or small consulting firm owner?

There are two questions in there. Why does politics matter to business owners? It matters a lot because politics is ultimately what determines the society that we live in. If you care about the environment or you’re concerned about climate change and stuff like that, that’s ultimately going to impact a lot of businesses in a lot of different ways. Some businesses are more than others in detrimental ways. That’s one way, for example, of why politics matters.

The pandemic that we’ve been through and are going through, how we respond to public health and how strong our systems are, that’s something that’s impacted businesses. It’s made an impact on how long businesses can stay open if we’ve been able to control COVID. In this country, Australia, we controlled COVID well for a couple of years. As a result, our economy was booming this entire time, whereas other places in the world were shut down and dealing with high infection rates. Business is downstream of politics. If you don’t take an interest in it, it doesn’t mean it’s not going to take an interest in you. That’s one way that matters to business owners.

The other thing is what can we learn as business owners from political movements? It’s a good question. I spend a lot of my time thinking about it oppositely. I came up through politics and movements. What can I learn from the business side of things because it’s not where I come from? It’s not my background. I didn’t study it or have a business-focused family. I learned a lot the other way.

What business owners can learn from politics is a lot about messaging, having a clear and strong message, whether you’re in service and what you offer in your marketing or whether it’s around your values and having a strong set of values and core values. One thing people get frustrated with politicians is they say the same things and lines over and over. It’s because you have to say something 8 to 10 times before someone will hear it and understand it. Something that businesses can learn from politics is picking clear, strong line statements of values and then repeating them so that your customer base comes to understand them.

There’s a powerful lesson in there that probably most people can apply. Very often, people aren’t clear on their messaging. They’re a bit wishy-washy and trying to go after too large of an audience. When you look at politics, people reference what happens in the United States. Whichever side you feel more aligned with, both sides always typically have a very clear message. One might win over the other but it’s that strong message that is repeated over and over again. Not trying to speak to everybody but trying to speak to a certain group of people tends to help one out.

That’s a great message for everybody joining in. Let’s go back in time. You went through your Law degree and started to get more involved in working with different advocacy groups, political groups and so forth. You started Defiance in 2017. What were you doing before you started your consulting business?

CSP 237 | Clear-Cut Offering


I was living in Vancouver at the time and was working for a political party directly as their Director of Engagement, which was at Vision Vancouver. At the time, the mayor was a member of Vision Vancouver and the city council had a majority of Vision members. We were the party in power at that time. I was doing community outreach, stakeholder relations, building volunteer networks and stuff like that. It was a great job with lots of awesome people.

One of the things about working in politics is it’s very cyclical. Not too many gigs go for more than 2 or 3 years because that’s how election cycles work. You get very used to moving on to the next thing. This is very common in the US where they have elections every year. It’s a little less common in Australia and Canada but it still happens. That was finishing up. I’ve been through this cycle a few times. We jump to the next role as you see through the election. I didn’t want to do that anymore. I was a bit burnt out on that.

Previously to that role, I’ve taken a bit of a detour from politics and worked in tech for a while. I worked for a political and civic tech startup called NationBuilder which is based out of LA. I spent some time in LA working at that startup. When I was looking to finish up in 2017, someone from that startup called me and said, “We’ve got this customer that’s using our product as a SaaS product and they need some help. Would you be open to doing a contract and some freelancing with them?” That was the firefighter’s union in Ontario, the IAFF. I said, “Sure.”

That was my first contract and the first thing that came to me as a consultant. I bet we were able to build everything over time around them. I worked for them for 2 or 3 years as a real anchor client and they were fantastic. It came to me by happenstance and I’m grateful that it worked that way. I then had to transition into going and working myself.

You got that first client through a referral introduction. What about the next 2 or 3 clients? Where did they come from? Was it also word of mouth and expanding that referral base? Were you in proactive marketing sales, need to get out there and bring in new clients? How did that come together?

It was a mixture of both. None have come so easily as that first one ever has, which was fantastic. They were ready to work with someone and I was ready to work. That was great. The next couple after that was within my professional network so folks that I knew or my friends’ friends or I’d worked with but I still went and said, “I’m doing this work. I’d like to talk to you about it.” It wasn’t marketing in the sense of building a funnel or anything like that. That happened later. In those early days, it was trying to have conversations with folks that were in my network.

During that time, what did you find to be most challenging? Looking back on the first few years of being in business, what concerns you most or is the toughest for you?

Looking back, I worked too much for not high enough fees. At the time, I felt that I’m not bringing in anywhere near as much revenue as I was when I was an employee, yet I have full responsibility for this fledgling business. That was the hard thing for me. Also, getting leads. Finding folks who are ready to go ahead and engage me took a lot of time. Reflecting, that’s because I wasn’t clear about what I offered, what I could do for them and what the benefits were. At the time, I didn’t know that.

I want to dive deeper into how your pricing strategy has evolved. Before that, let’s talk about how your offerings have shifted. You mentioned some of the things that you’ve been working through. Break down for us, what did things look like before when it comes to your offerings? This is a challenge that so many consultants find themselves in where they could offer a lot of things to a lot of different people. Walk us through what your offerings looked like before and then we’ll step through this together.

Business truly is downstream of politics. Just because you don't take an interest in it doesn't mean it won't take an interest in you. Click To Tweet

To be quite honest, in the beginning, I didn’t have a set offering. I have a general area in which I practice but I didn’t have a set number of offers of things that I would roll out and do for folks. For example, I work in the field of politics, advocacy and unions which at that time, organizations were not at what I would call digital maturity.

They didn’t have strong digital systems in place. A lot of stuff was done ad hoc. Folks didn’t have a lot of internal capacity to implement new software products or approaches. I was a smart guy who knew about digital stuff and could help you if you had a problem with digital stuff, which is incredibly squishy and doesn’t attract people.

I would do all sorts of different things. It may be from writing emails to their list, running an entire campaign, including landing pages, your petitions, texting their supporter list and getting people to take action. I could hold the whole campaign or give some advice on strategy for the campaign that folks wanted to run. It was very broad. I put the onus a lot on people to tell me what they wanted me to do rather than me coming to them and saying, “Here’s what I can do for you.”

What were the challenges that you found when you were doing so much custom work? What were some of the issues or points of resistance that were coming up for you?

Some of the challenges were that every time I would need to put a proposal together for someone, it would take a huge amount of time because I’d be reinventing the wheel every single time. I’d be writing a custom proposal document and be thinking, “How much work is this for me? How much should I charge for this? I don’t know.”

I got away from hourly billing early on, even before I started working with you and the consultant success team but that still didn’t help me because I didn’t have structured pricing in place. I’d have to think about pricing every time. When it came to implementation, doing the work for clients, I wasn’t getting any efficiencies of scale because I was never repeating the same process over and over. Things would take longer.

If we fast forward from you doing a lot of custom work, the more recent version was you had set offerings but you had more than one set offerings. Can you talk a little bit about what that looked like in the most recent? Not where you are now but before that, what did things look like at that point?

If I think about my work in three phases, there’s that initial phase where everything was custom and I was a contractor. The next phase is I thought of myself as a freelancer. I worked with multiple clients at a time and had a little more specificity around my offers but they were in a range of different areas. I developed a bit of a fundraising specialty where I could do digital fundraising for folks.

I also had some stuff around internal development and change management around digital processes and technology for progressive organizations. I had a few different streams. One of the upsides to that was I had more clarity than before. I was able to provide more clarity to potential clients and attract a broader range. It was outweighed by the difficulties which became evident when I was working on my website and trying to put a very clear message on what I do and who I do it for.


I had a couple of different things I did and you can’t put that on a page. When you’re in the backend of Squarespace, have to write it out and say it, you end up looking like you’re trying to do everything, even though you feel like you aren’t. I ran into problems with marketing without having too many offers. The main challenge was around marketing and being clear about what I did.

That was chapter two. If we look at chapter three, what does your offering look like?

My offering is wholly related to raising money and building power online. I have a standard set of three offers, where there’s an investment on the lower end, which gets folks custom-written strategies for them that they can then take and implement themselves. My second offer is around, you get that strategy but also my guidance on an ongoing basis for 3 or 6 months, coaching your staff one-on-one and helping you implement that strategy.

I’m not doing it for you but I’m helping you do it and making sure you stick to best practices. The third offer is the full-service offer where my team and I will do this for you. For example, if a political party doesn’t have a digital fundraiser or a digital team in-house, we will take over their email so we email clients and take over their properties and run it for them. Those are the three main offers.

On top of that, as an introductory or discovery offer, I have an assessment tool which folks for an even lower level of investment or an entry-level investment can get a snapshot from me of where they’re at and some recommendations for where they might go next. There are the three main service offerings and then sometimes a discovery.

As you’ve made that shift ultimately to narrow in and say, “This is the circle that I’m going to play in and here are the very specific ways that I can engage. I know this work. I’ve done them for others. I can create great results and value,” and setting your pricing around that, what have you experienced in terms of your mindset, marketing and results? Walk us through what are the benefits that you’ve experienced since narrowing in on that.

Before I talk about the practical benefits for the business, the benefits to myself and my mindset have been huge. I don’t think I realized how scattered I had been feeling for the years before when I was trying to offer too many services, serve too many people and be too many things to too many people. I don’t think I realized until I narrowed things down how much of a drain that is on you.

Now that I’ve narrowed in and focused on a service offering in an area that I’m passionate about, it also gives me space to spend more time learning about that, becoming a better expert at it and getting better at it. Whereas before, it felt like there were too many things going on that I couldn’t spend time doing. My mindset has been huge. It’s also given me a huge amount of confidence when I speak to folks about what I do because I can be very clear about what I do and don’t do.

For a lot of consultants and this was the case for me, what you don’t do is hard because you’re worried about losing people or if someone says, “Can you build me a website?” “No, I can’t build you a website. I can refer you to someone great. That’s not what I do.” I’m comfortable saying that. That’s been my mindset shift. On the business side, I always found it hard to do marketing before when I was in chapter 1 and chapter 2 when things weren’t as clear and messaging was a bit squishy.

Don't lock yourself into a fee rate that stops you from reinvesting into your business so you can grow the business. Click To Tweet

Whereas now, it feels like that’s been unlocked. With my email list, for example, I can have a clear welcome series when someone signs up on my website. That is three emails that tell them exactly what we do in Defiance. Whereas before, I had to hedge a little bit and keep that broad. Now I can be focused on it. If someone is looking for that, they can unsubscribe. It’s a lot more authentic to the audience as well. The biggest benefit has been in marketing and having those structured offers and pricing.

As you’ve gone through those chapters, chapter 1, chapter 2 and then chapter 3, have there been any shifts around your pricing strategy and how you think about your pricing?

There has. My pricing is more static. I don’t have to price every project anymore, which was something I was doing before. When you price every project, you end up in the position where you’re negotiating with yourself every time and you’re negotiating yourself down, quite honestly. No consultant sits at their proposal document. They get to the end, got the price line, write it in, delete and put it back. We all know how that works.

You knock it down a bit and they bump it up a bit. In the end, you always come in lower than you intended when you started. There’s something about us that we undersell ourselves. When you have set pricing and review your pricing every quarter or something like that, it’s not to say your pricing never changes. You say, “This is what I’m going to run with for the next few months.”

You’re not going through that process all the time so you’re not undervaluing and underselling yourself. That’s important for early-stage and people who are coming out of early-stage consulting, which is where I am. Make sure you don’t lock yourself at a fee rate that doesn’t give you any room or margin to be able to reinvest back into the business so you can grow the business. Otherwise, you end up becoming a freelancer again.

I’d love to get more into that. Before we do that, one other thing that you’ve also developed is the Defiance Digital Action Model. Why did you create this model? How has it helped you to have a model, framework and image defined?

The Defiance Digital Action Model is my approach based on my years of experience working in the field on the core elements of what makes a good digital fundraising strategy or digital engagement strategy. It can be applied across different industries. It works for my union clients, political clients and advocacy clients.

It gives people a reference point to, “What are the five key things I should be focused on? What comes underneath them?” If that’s up on the website, people can have a look. There’s more underneath that I get into with clients. What I wanted to do was I wanted to stop reinventing the wheel every time I was having conversations with folks. I wanted to lay a marker down and say, “This is what I believe and what I think is important at this point.”

It will evolve as everything does. It’s given me a structure to approach my work and engagements with clients and say, “Here are the areas we need to hit. Here’s where you’re doing well and not doing so well. Here are some things you can do to improve in this area.” It provides a structure for my work and my clients to understand where they’re at.


We’ve also developed the Consulting Success Framework and have a visual around that as a way internally to think about it and think about how we structure content, training or materials and best practices. Also, as a way to have more structured and valuable conversations with confidence with clients and buyers to be helpful.

The other thing that I’ve noticed with you over time is you have a real focus on balancing building the business while also being a present father and family man. What lessons have you learned? How do you think about those two things together for others who might be in a situation where they’re being pulled in one direction or the other a lot?

We’ve had conversations about this because we both have young kids. It can be challenging, to be honest. I don’t think the last few years have made it any easier. It’s been rough for everyone. Maybe those of us who are used to working at home with an empty house suddenly got used to working from home without an empty house.

The way that I think about it is back to the first principle, “Why am I doing this? Why am I building this business? Why don’t I just go get a job somewhere?” The answer is that I want a type of lifestyle that means I can be present for my family and do the things I want for myself and with my family and still build a business, have a career and generate income as we need to do.

If I was to allow the business to take over the family time, time for myself and my wife, then I’d be betraying the whole reason I was doing this in the first place. I may as well go get a job with structured hours, vacation and superannuation/pension. I have to keep checking in with myself and say, “The reason I’m doing this is that I’m trying to build a life that includes my business, my family and myself. If I start straying away from that too much, this is the reason I’m doing this.”

That is why it is so important. I’ve seen it come back for so many clients over the years where at times, you can lose the bull’s eye of the why. When you get into different situations, whether it’s not doing your marketing, not doing something in your business that you shouldn’t be doing or spending too much time on something you shouldn’t be, it’s always getting back to the why. It helps create that clarity or bring you back to the center. I appreciate you sharing that.

Jack, has there been anything that you’ve been working on that you feel has been a real big win? Aside from your talk lists, the shift and offerings that you’ve worked through, which is a big one, is there anything else that you’ve learned or anything else that you feel like, “This has had a big impact on the business or me as a business owner?”

Aside from the specialization and allowing me to narrow down the office, I would say the biggest thing that I’m moving towards is getting some help, building my internal team and not trying to do everything myself. I’m at the point where I have a couple of contractors who work for me, whether it’s on administration support, helping with my marketing or automating a bunch of my marketing work. That’s previously stuff that I would have done myself. I would have taken the time, which is a significant chunk of time because that’s not what I am professionally.

Administration, for example, is something that anyone can do. Why would I pay someone to do that? It’s a specialty. Some people are good at it. I’ve done it a lot. That’s not me. I technically can do the things that my VA does but she does them better and faster than I would do them. Why wouldn’t I have an expert help me with that the same way I have an expert to help me with my marketing, accounting and legal?

Learning to say no can be empowering. Click To Tweet

Do you remember a point in time where that clicked for you? Do you always feel that way? Is it a sign that’s become a realization at some point where you said, “I should not be doing this any longer. I need to stop doing this?” What was that transition point or point of shift for you?

I’m smiling because it happened midway through 2021. I was going through receipts or something to send to my bookkeeper. I’m trying to find Amazon receipts. For anyone who uses Amazon, they annoyingly don’t send you an email of receipt when you purchase something. You must log in to Amazon to get your receipt. It’s annoying. Amazon should fix that if you’re reading.

I was like, “Why am I doing this? It’s taking me a lot of time. In this time, I could be talking to a client, having outreach to someone that I want to work with or writing an email to my list of all these things. Why am I doing this? This is frustrating.” From there, I spoke to some other folks in the Consulting Success community about how they’ve got some outside help and I took it from there.

It’s a stop-start. Sometimes you work with a few folks and find the right fit. It’s not always from day one where everything’s great. You must work on the stuff. I stuck with it but I’ve got a good place. I want to free up time to do the generation of business and honestly to do other things. I like to cycle. I maybe want to go for a bike ride instead of going through Amazon receipts.

If you look at your productivity and performance, what do you feel contributes most to the success that you have regularly? What are 1 or 2 things that you typically do or a habit that you feel has a big impact on that performance and productivity?

The number one thing is physical activity and exercise for me. I’ve noticed in my life, at periods where many of us struggle with, mental health, feeling pressure and stuff like that, it’s physical activity and exercise that help pull me out of that. Maintaining that baseline of exercising 5 or 6 times a week makes me productive. It also gives me an incentive to get done what I need to get done that day because, at 3:00, I got to go work out. That’s non-negotiable. I’ve got to get it done. I find physical activity to be helpful.

I’m with you on that. Although for me, I like to do it in the morning before everybody’s even up. Otherwise, if it gets to 3:00 PM or 4:00 PM and I’m finishing the office, the day for me is done. It’s back to family time and all that. Good for you that you can make that happen. I’m often like, “I’m tired. It’s time to relax.” Jack, is there anything that we haven’t talked about relating to your journey thus far, in terms of things that you feel are best practices and lessons learned that might be helpful for those that are reading?

I was thinking that something has changed for me. I’ve learned to say no to things and particularly say no to requests for work that don’t align with where I want the business to go, even if they’re quite lucrative. That’s hard. For sure I can relate to folks that say, “I don’t want to do this work but I don’t want to turn it down because maybe in the future, this client could be a good client XYZ.”

I’ve learned that saying no to things that aren’t within your plan, the plan for your business and the way you want your business to go is empowering. Once you do it, it’s a good feeling and you think, “I can do that again.” All of a sudden, you’ve cleared the decks of these engagements that are draining for you and maybe don’t make a lot of sense for the business or you. Say no to things if they don’t align with your business strategy and values, which is another important thing. Learning to say no can be quite hard as a new consultant but it’s a good skill to master early.

CSP 237 | Clear-Cut Offering


In my experience, it doesn’t matter whether you’re an early-stage consultant or you’ve been consulting for 5, 10 or 15 years and whether you’re running a $100,000 a year business, $1 million, $2 million, $3 million or $5 million business. The more “successful” or established you become, you tend to even have more people, things or opportunities vying for your time that are exciting.

That’s where it becomes even more important to say no because you only have so much time and you want to make sure that you’re putting that time into the things that matter the most. I appreciate you sharing that. Two more questions Jack before wrapping up here. What is the best book that you have read or listened to? It could be nonfiction or fiction but it’s anything you’ve enjoyed.

It’s called The Premonition. It’s a nonfiction book. It’s not business-related, although it has some implications. It’s the same guy that wrote Moneyball. It’s about the initial response to the COVID-19 pandemic in the United States, particularly around the shape that government institutions were in when COVID hit in the US and all the failings of the system. They weren’t individual failings. They were system failures in the way that the US had set up its health system. That meant the US had lost the battle against COVID before it even started.

What was so interesting about that was how important the systems are that we set up around us, whether it’s government and politics or in our businesses down to a small business like a small consulting business. If you don’t have the right frameworks in place, when a crisis hits or an opportunity arises, you won’t be able to take advantage of it. For me, there are a lot of lessons in that book, The Premonition by Michael Lewis.

The final question but very important is, for those that want to learn more about your work, check out your content and even connect with you, where should they go?

They can go to

Jack, thanks so much for coming on and sharing your journey with us.

I appreciate it. Thanks, Michael.


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About Jack Milroy

CSP 237 | Clear-Cut OfferingJack has spent a decade and a half building and scaling campaigns using technology. He has worked on elections and advocacy campaigns in Canada and Australia, developing a people first approach to campaigns, organizing and fundraising.

Jack has worked as a strategist at leading progressive organizations in Australia and Canada:, the Labor Party, the United Workers Union, and the NDP.

In 2015 he joined the team at political technology startup NationBuilder, working from headquarters in Los Angeles. In this role he worked with customers across the US, Canada, Australia, NZ, and South East Asia to leverage technology to scale impact and campaigns.

Now, he helps movements raise money and build power online.

Working with:

– Australian Labor Party
– United Workers Union (UWU)
– International Association of Firefighters (IAFF Ontario)
– Canadian Union of Public Employees (CUPE BC)
– International Federation of Journalists (IFJ – Asia Pacific)
– $10aDay Child Care Campaign

If you’re interested in learning more send me a message, we’ll set up a time to chat!


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