Working Without Pants - Creative Entrepreneurship

To experience the freedom that entrepreneurship can provide, you need to learn how to let go of certain responsibilities and let others lead. 


In this episode of the Working Without Pants podcast, I provide some tips on how to let team members take ownership of more responsibility and what that process looks like. 


In many cases, people confuse delegation with letting others lead. Delegating new tasks can be a step toward moving someone into a different role, but you’re still overly involved in the process. The goal is to have others take complete ownership over their role without your daily guidance. 


When moving someone into a manager-type role, it's best to set a hard deadline for when they are expected to fully take charge. It's okay to provide occasional support but you want them to be able to problem-solve on their own.


During this process, you should provide a detailed job description, clearly define a team member’s new expectations, and outline what success looks like. If problems do come up, try to avoid immediately jumping back in. If you are always there to come to the rescue, your new leader will stay reliant on you.

Want to work with me as an advisor? Visit


This episode is brought to you by Zapier


My companies could not do what they do without Zapier. We use Zapier to automate tasks and connect all of our various web applications together. It could be connecting Airtable to Slack, our invoicing software to Airtable, our Project Management tool to Payroll… the integrations we use it for are endless. If you aren’t using Zapier, get on the bandwagon and try it out at

Direct download: WWP_-_Leading_others_and_letting_go.mp3
Category:For Agency Owners and Consultants -- posted at: 12:00am EDT

There are many shifts you go through as an entrepreneur. And there most definitely will be a time when the tactics and mindsets that worked for you previously will need to be updated in order to level up.


In this episode of the Working Without Pants podcast, I discuss the importance of continuing to evolve as an entrepreneur and why there are always new challenges awaiting you throughout your entrepreneurial journey.


Many entrepreneurs think things will get easier as they reach certain milestones, however, new problems show up at each level of entrepreneurship. Just when you think you have a skill set mastered, things get challenging again when more money and business scale are involved. If you try to rely on the skills and attitudes that got you to this point without further growth, you’ll not only halt progress but actually shrink when faced with new market and business conditions.


For these reasons, I highly recommend working with an advisor or coach who has been through the different stages of entrepreneurship. They will help uncover your blind spots so that you’re able to evolve and tackle the next stage of your journey.


Want to work with me as an advisor? Visit

Direct download: WWP_-_What_got_you_here_wont_get_you_there.mp3
Category:For Agency Owners and Consultants -- posted at: 12:00am EDT

Digital agencies are very different from traditional businesses, thus buyers and sellers of these agencies need to approach M&A in a particular way.


In this episode of the Working Without Pants podcast, I sit down with Amanda Dixon, co-founder of Barney, to discuss how agency owners should be thinking about M&A to maximize their exit. We also talk about what buyers are looking for when acquiring digital agencies.

Amanda shares that M&A for digital agencies requires a different approach because the focus is on the human capital of an agency versus tangible assets, which is the case with many traditional businesses. She also notes that sellers of agencies are typically younger with long careers ahead of them. This creates unique deal structures.

To minimize their risk, Amanda says buyers prefer agencies with a lot of recurring retainer revenue and a more robust management team. Smaller freelance teams with project-based revenue are inherently riskier for buyers.

For agency owners looking to sell, Amanda says not to be scared of scaling up before your exit. Reaching a few more key financial milestones can go a long way for increasing your multiple on the sale.

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Direct download: WWP-barney-v2.mp3
Category:For Agency Owners and Consultants -- posted at: 7:32am EDT