In this episode of the Seeking Scale podcast, co-hosts Craig and Andy dive deep into the trials and tribulations of entrepreneurship, sharing their insights on effective delegation, strategic planning, and the art of maintaining focus. Craig kicks off the conversation by sharing his experience of a team retreat in Athens, Greece, emphasizing the complexities of ... Read more

Craig and Andy begin by talking about the weather and what’s been happening during the past week. Craig says he’s finally feeling recovered from traveling, and Andy discusses the illnesses his 4-year-old has been dealing with for the past few weeks. He says that this has helped him focus on only what’s most important for ... Read more

Craig and Andy discuss a Twitter interaction that they had. Craig tweeted about wanting a tool that shows trials month-to-date and how it compares to the previous month. Andy wonders what he would do with that information. Andy thinks that it’s too much noise and that this might not be the best comparison to make, ... Read more

Andy says he’s feeling a little manic and running on a lot of caffeine. Craig says that things are looking better from where he is. Trials are up in the last few months, and sales are up as well. This is due to some changes that are starting to pay off. Craig and Andy discuss ... Read more

Craig says he’s been writing more, including starting a newsletter and working on his personal website. He’s interested in the intrinsic benefits of writing. Craig also wants to invest more in himself. Andy wonders if Craig writes much in general. He explains that he doesn’t journal, but when brainstorming, his default is to write it ... Read more

Andy talks about the good traction they’ve had recently that’s starting to show now. They just shipped a big update and received a great reaction to it. It came together faster than similar things have in the past. Craig explains that Castos launched a free set of tools that’s starting to get traction now. Andy ... Read more

Today Craig and Andy discuss how to think about options. Andy talks about making sure everything is ready for a large influx of new trials. They’re already up 140% over last month, and he says people are more likely to buy in mid-season. He talks about taking on too much and learning about prioritization as ... Read more

Craig and Andy discuss the importance of prioritization and the importance of capital efficiency. Craig explains that Warren Buffet cites Apple as an example of a capital-efficient company and wonders about whether his company is a capital-efficient company. Andy says that often, people spend much of their time doing things that have no meaningful impact ... Read more

Andy and Craig talk about social media strategies for their respective brands—SaberSim and Castos—related to the HubSpot State of Inbound Marketing Trends 2022 Report. Should they be doing more on social media? If yes, what and how? Is it worth it? People do not follow brands but individuals and influencers on social media.   Craig stresses the importance of putting out and optimizing marketing content that is effective on social media channels to grow the audience, make a positive business impact, drive trials, and expand/expose brand to equity.  Andy is skeptical about social media. He encourages Craig to not force social media if that is not his strength. Instead, hire someone with the necessary skills to build authority for better results, consistency, and success.

Andy and Craig talk about product-led growth being the most dangerous movement in SaaS startups. To convert, a product needs to be built that is relevant to the intent of SEO for growth-led products that deliver on what’s promised.    Andy rants about a tweet on product-led growth companies building products that sell themselves. However, Andy clarifies his thinking about how product-led growth does not exist. At best, it emphasizes the wrong part of the growth engine. At worst, it legitimizes the mentality that if you build it, they will come.  Craig believes a lot of the same things and addresses the virality of product-led growth. Running a good business and having a good product is 95% of solving a problem and only 5% is the viral coefficient. The dangerous thing about product-led growth is that a great product by itself will never sell. It still needs marketing content or the company and product will likely fail.

Andy and Craig talk about focusing on delegation, prioritization, and productivity. Based on feedback, a lot of stuff that people do is not really effective. What tools, books, and other resources do they recommend? Andy’s been busy leading up to and since the birth of his baby. He just can’t do everything at work and some things will not get done⁠—but his new assistant, Madison, who was found via Great Assistant, is holding Andy accountable. They work together to handle his inbox, and she forces him to respond to messages until more is delegated. Craig thinks an assistant would be very helpful and has been looking at Zirtual. However, an assistant is only successful if he is willing to spend time or is forced to make time to work with them to delegate and be more productive. Also, Craig has been more active on Twitter and posts about business, marketing productivity, and delegation.

Craig and Andy talk about learning to just say, ‘No.’ What is meaningful, matters most and what does not? Most likely, 20-50% of what you are doing are things that you should not be doing.  Craig shares how his company retreat went really well. They dedicated time to talk about and reflect on objectives and key results (OKRs) as well as gaining opportunities by focusing on one thing. The outcome for good ideas comes down to certainty versus effort.  Andy is stressed out because he likes to control everything, but the countdown to baby due date is fast approaching. At the company, he is working on priorities and getting processes in place, but some things have to be postponed. Eventually, he wants to have a company retreat.

Craig and Andy talk about finances. But first, founders need to give themselves permission to do what they want to feel better and guarantee a great start to the workday because too often the afternoon falls apart. Craig wants to declare that he does not start work until 9 a.m. to drop his kids off at the bus stop and workout despite the little green dot in Slack or email tab in Chrome (refers to Atomic Habits by James Clear). Andy agrees that finding routines, establishing habits, and not making excuses should be a priority.  Also, Andy and Craig explain their rationale for switching bookkeepers/accountants. Craig is over Bench and going with GrowthLab FInancial, and Andy went back to Pilot because of ongoing problems with handling books and lack of responses to requests.

Does your marketing have a defined purpose, structure, or place in the funnel? If not, then you should not be doing it because it’s ineffective, creates noise and uncertainty for prospective customers. Craig and Andy revisit cohesive marketing.  There are stages that people go through to become a buyer. Andy has brainstormed and thought about focusing on marketing strategy, cohesive marketing, and content to make sure everything fits together in a funnel.  Craig believes that every piece of content on his site is different and has a different job—not a one-size-fits-all approach. Content campaigns should be created to nurture, offer a lead magnet, and understand customer personas/segments.

Craig and Andy talk about pre-planning versus figuring things out as they go. What’s driving what and how do you get there together to grow? After a weekend getaway to unwind, Andy is back to prep and quarterly planning before paternity leave. Focusing on the right things makes a big difference because it’s so easy to get off track. Craig is planning a company retreat that will include strategic thinking, intentionality, shop talk, and making connections with coworkers. Also, Craig has been working with a business coach to help him avoid decision fatigue as a founder.

Craig and Andy talk about the shift in mindset when it comes to taking time off from your business and getting others up to speed or being more productive and strategic as a founder to enable others to reach goals and be successful. Andy’s stress level steadily increases as the due date nears for the birth of his baby. His mindset has shifted from creating new stuff for SaberSim to more productive tasks, such as planning and priorities to wrap up projects before he takes time off. Craig’s management style tends to be very laid back and less stressful. So, his team met up for a retreat to lay out a more structured approach to feedback and reviews using the continuous performance management software, 15FIVE, and project management software, Notion.

Craig and Andy talk about building for now versus for the future when it comes to their roles and responsibilities as founders. Both are looking to take themselves out of the critical aspects of their businesses. Andy is focused on significantly shifting what he is working on and hiring an executive assistant and copywriter before the birth of his baby. Time is limited, so he may not be able to hire and onboard until after he returns from paternity leave.  Craig provides an update on his business about hiring specialized attention, focus, and talent for what really matters and is most valuable to the company and customers. He has realized that he is too involved in services over product. Castos is now hiring a podcast coach!

Craig and Andy talk about current events in tech, including Paddle’s acquisition of ProfitWell and what else is going on in the bootstrapped versus enterprise world, economy, and ecosystem.  Andy views the acquisition/merger as the ProfitWell brand and team continuing to do what it has been doing, but what will happen to the leadership (i.e., Patrick Campbell) and liquidity? It takes money to grow a business, but don’t obsess over numbers you can’t control.  Craig explains that ProfitWell’s product revenue is 80+ percent of the company. This is the path to take if you don’t want to raise money, start as a consultancy, build a product, revenue shifts, and roll over profit. That’s what Craig did, too.

Craig and Andy talk about refining the hiring process and lessons learned. Get prepared and things ready, but it’s still not going to be what you expect it to be. Andy and his wife are expecting a child. So, he is wondering how he’ll handle being a father and founder. He needs clearly defined processes and know what’s most important to hire, onboard, and assign priorities/tasks. Andy, especially, wants to hire an executive assistant and copywriter. It’s been years since Craig’s children were born, but he explains to Andy that he should not expect to travel for business or work a full schedule. Hire someone and put processes and expectations in place to take care of things that need to happen on a regular and timely basis.

Craig and Andy talk about managing technical debt. Is more data needed? Do you need to be driven by metrics? What is possible versus realistic? Who do you need to make happy—your customers or your team members? Andy shares how a big release has been in quality assurance (QA) for about a month, which shows the shortcomings of the product process but pushes for better quality when released to the public as refactored, not redesigned. Craig understands how the product process is never done. There’s always some metric or issue to track, improve, fix, and measure. Also, as the owner and founder of Castos, there’s times when team members are hesitant to push back or share their opinions on what can be done.