Documentation, Event

73 Min Read

Documenting Processes and Building Communities on The RevOps Review Podcast

Thank you to Jeff Igancio for inviting me to the RevOps Review podcast to talk about documenting processes and building community! 

The show covers these topics (which link down to that section of the blog):

Listen to the podcast below, or keep reading!

I don't expect anyone to read this entire giant blog, please use the links above to scroll down to what you're interested in.




Revenue operations journeys 


 Jeff asked about how I got involved with revenue operations folks, how I started building content for them.
The agency I worked for in my previous full-time role started as a marketing technology agency. When RevOps became a popular term in 2020, we realized that's what we were actually doing, so we were rebranding to call ourselves a RevOps agency. That was also when I started more of an official operations role. So I went on a deep dive to learn about operations and RevOps. I found communities, and that was a new thing at the time, having that Slack workspace type of community. And that was super helpful for learning common questions and answers for problems in ops, and helpful because a lot of operations information is not really easy to find on Google. I usually found supply chain information when searching... that's not super relevant to what I was doing building a small agency.

I joined these communities and realized there was a gap in the market for certain information that I wanted to help share, about topics like documentation. Topics that are not talked about a lot. I wanted to try to help other people so they don't have to build from scratch and go through this whole trial and error process and research journey that I went through.

Jeff described his journey, starting in sales in high school. "I joined this Cutco knife thing and trying to sell to friends and family. I was a cold caller, an SDR really, for Merrill Lynch. My cousin had worked at Merrill Lynch as a wealth manager... after management consulting, I went into headhunting recruitment, agency recruiting sales before going into business school and then flipping the script and taking a totally different career. In 2013, when I first came into ops, I realized that there wasn't a whole lot of information. And I had to learn everything from scratch. The role was very technical back then. So I had to learn from Stack Overflow YouTube videos, asking folks how to do things and that's how I learned all the systems side of the house and revenue operations. But nowadays, 10 years later, there's a whole slew of information: newsletters, [courses], podcasts... And so it's a great time to get into revenue operations because you don't have to reinvent the wheel."

Learning revenue operations through online communities

Jeff asked which communities I dug into and if I felt like an undercover cop on patrol.

There was a joke at Remotish (my last company) that I was always 'spying' everywhere, using the word spying in a joking way. But that's kind of what I do, spying and lurking in the Slack workspaces to spot trends and common questions and answers. 

I do remember specifically joining Pavilion, that might have been one of the first I joined. And because I'm an introvert, I need to have a 'job' when I join any kind of networking, for in person events especially. So I volunteered to be an associate chapter leader when those events were returning after COVID shutdowns.

There was also Wizard of Ops, MoPros, RevOps Co-Op, Operations Nation...there's so many that were all gaining momentum around the same time, or at least I discovered them at the same time. And it's just great to see so many operations communities.

Jeff said he joined Pavillion back in 2020, at the behest of a former superior, Justin Welsh, current content titan. At the time, Justin, Jeff, and Kevin Dorsey were all on the same sales leadership team, and posting on LinkedIn together. "The pandemic hit a year later, and all of a sudden, we were some of the few people who are riding a wave of this trend of folks consuming content...people had shifted their social media habits to LinkedIn. That was really interesting, and we just happen to be at the right place at the right time," he said. 

Jeff also thanks RevOps Co-op for being a great partner, and called out the live events they are organizing, as well as giving a shout-out to Mike Rizzo for's Mops-aPalooza event. 

Read a little more about community involvement in the prep notes.

Course creation and iteration


Jeff asked, "Tell me about who takes your course. What have you learned from the students, because you're a facilitator, you're teaching folks, but at the end of the day, you're also learning from your students."

My current courses are for process documentation. I have a full suite of products about documentation, but the main one is the 'How to document your business processes' live course that has four sessions.

I did a live course first, to get faster feedback for what you mentioned, learning about improving. I made a lot of the sessions longer than the beta version. I think they're 90-120 minutes instead of 60 minutes now, because people wanted more time for the individual work and breakouts during the sessions. So that was a big lesson about giving people more time to do work on their own and to work with each other for that collaboration.

Bonus notes: I originally ran them on Tuesdays and Thursdays but people wanted more time between sessions to complete the homework. Now they are Tuesdays and Fridays for two weeks, and I'll be testing a once-a-week for four four-week schedule soon.

I also learned which topics of that course were most popular, so I spun those off into one-session workshops about writing documentation and setting up your documentation systems. So that was an interesting learning because some people might only be interested in that one topic and they might be hesitant to take a whole four-session course. 

I learned that some people just like using the workbook and maybe not taking a course, so I made the workbooks available on their own.

After doing all this iterating from all this feedback and all this learning, I made an on-demand course recently for people who may not be in a convenient timezone for me to teach live. I know time zones were always an issue. I've been switching up the time in the class based on all the surveys that I run, to give people a chance to fit it into their schedule.

I asked Jeff if his classes ran into time zone issues with students, and other learnings from running classes.

Jeff runs two courses in two formats, live and on-demand.  

  • Unleashing ROI (on-demand for RevOps Co-Op and a live version on Maven)
    • ROI here means RevOps Impact since Jeff believes that revenue operations does return an investment to businesses 
    • Running for about six quarters with RevOps Co-op, with over 100 students last year
    • 10 weeks and 10 hours of content
    • Good for teams of one or aspiring RevOps leaders who want a 10,000-foot view of revenue operations
  • Sales Ops masterclass
    • Over 65 students
    • 12 weeks, six-session deep dive into sales operations
    • 6 hours of content
    • Aimed at individual contributors looking to execute the work
Read more about how and why the courses were created in the prep notes.

Class member profiles and problems to solve

Jeff said his students have been all over the world. In the beginning, it was mostly North America, Canada, and US, though recently, some Asian students have enrolled despite the 8-9am Pacific time start of class.

He hasn't yet experimented with changing the time zone but thinks an Asia-friendly time would be a good rotation, when there are more students per cohort. For now, the other time zones can experience the on-demand class at leisure at home.

"I think at some point, I'll probably just have a deep fake version AI version of me, people can interact with that virtual avatar. And then I'll be everywhere, I can service all sorts of different formats," he joked.

For my documentation courses, the students been mostly on the US East Coast in Europe. Mornings in Pacific time zones have been most popular. The bootcamp I run for HubSpot at 8am Pacific time has more of a global audience, with some people joining in the middle of the night in their timezone, which shows dedication. 

Jeff talked about the budgets that people use to pay for his courses, usually from corporate learning and development budgets. He compared it to the health savings account budgets with the email reminders at the end of the year to spend it before you lose it, that's some of the messaging he's used. He also discussed lowering the price enough and using payment plans to capture some personal spending on the course.

"I, for example, pay for several memberships myself. I try to allocate a certain percentage of my top-line income, this is an investment for me. If I can get my company to pay for it, great, if I can't, and I'll pay for it out of pocket. And I find that the education for certain roles like revenue operations, you're just not going to get it from your workplace because most of the're the only person probably doing revenue operations, then who are you gonna learn from?" Jeff said.

I've only been running the documentation courses for about a year [as of this recording] so I'm interested to see what happens in January, if more people are going to sign up because budgets got refreshed. It's been a mix of personal and corporate spending on the courses. [Update -- yes, the first cohort of the year was the fullest one in a long time.]

Jeff asked what percentage of my class members are in revenue operations.

I haven't been able to track it precisely yet but I would say 30%, because a lot of my network is revenue operations or marketing operations. Otherwise there are a lot of agency people because that's what is my network from being in agencies. Another persona is founders or solopreneurs, who are looking to expand their team and delegate more of the work, so they need to document. [Update -- all 7 people in the first 2024 cohort were in revenue-operations-related jobs]

Jeff talked about how the weight loss industry will show the before photo and the after photo, he asks RevOps people to show their tech stack before and after, or their processes before and after class. He asked what's the journey before and after for my classes.

Before classes or before documentation, people are really stressed because they have way too much work to do. They have to remember all the information about the 10,000 things they're doing every day. If they're either a founder or any kind of operations team of one, they're probably doing different things every day. They may only do those things once a month. It's pretty hard to remember how to do things without either recreating the wheel, having errors, or just being stressed all the time.

The after-documentation state would be having less stress because they can delegate and spread out their work. Less stress, because they don't have to remember everything and can just refer to that document. They don't have to worry about missing a step. They can learn how to improve those processes now that they can see them, so they can do their job better or get promoted. And there are many other benefits, but we've got limited time, so I'll stop there.

Documentation and AI tools for revenue operations



Jeff said he thinks about documentation like job aids, standard operating procedures (SOPs), rules of engagement, and naming conventions.

"For example, if a sales rep asked me, 'Hey, Jeff, I'm curious how to manage this opportunity in Salesforce?' [I'd say] 'Great, let me point you to our wiki or on our Confluence page, or a Notion page, or here's a Loom video.'" he said.

He asked what were some of the most common tools that some of my students have shared for how they document their processes.

It's been interesting because so many people use different tools. And I encourage that because it depends on the tools you're already using. What's going to integrate into what the team is already using as their daily home-based tools so they don't have to learn a tool in addition to the new habit of doing or using documentation? Because those two things together create twice as much adoption work to try to get people to do it.

Some of the popular tools have been Notion, ClickUp documents for the agencies who use ClickUp already, and the HubSpot knowledge base which is what I used at my past agency because we were a HubSpot agency. So that made sense for us, our people were in HubSpot every day. Why don't we put the documentation where people are already working?

Jeff discussed some of the tools people used to run courses, such as Kajabi, Udemy, and knowledge bases.

Jeff talked about using a chat base tool Sean Lane sent him, feeding in his newsletter articles to train it to answer questions as a chat bot. He asked if I use generative AI for anything.

I haven't done much yet, but I'm keeping an eye on it. I've heard in my classes that people have used it for editing their documentation, like doing a first brain dump of the process, and then they'll use AI to clean it up. And then after people have documentation they've mentioned making a chatbot that pulls from that documentation that answered people's questions, so they're not answering questions all day. So that's freed up their time.

Jeff said it sounds like an Alexa or Siri companion, or a fancy Clippy tool.

Building a community and content flywheel

Jeff asked if I thought about building a community for course alumni who want to stay involved, or how I'm thinking about community.

I have a Slack workspace for alumni. I wouldn't call it a community because it's so few people right now, I haven't had enough class members yet. But I do share the pieces of my newsletter, that are specifically related to documentation. I'll schedule those posts for one a day, so people get those resources. I ask people questions in there and try to get feedback on the course. In addition to a cadence of 1, 3, 6, 12 months surveys after they take the class. 

I asked about some of the combining Jeff had been doing, moving all of his educational content work into Substack.

Jeff said, "The idea is to create a flywheel have these assets, these pieces of's sort of a tiny media business that I run. The newsletter goes out on a weekly basis. That's two hours of writing on Sundays. The podcasts I'm recording, maybe two interviews per week... that's about two hours as well. So I try to keep all the side businesses to only five or six hours of work [per week] and pushed to some hours that are friendly for me to be able to balance a full-time job."

Jeff continued, "The whole idea is to have a newsletter point to the podcast and the podcast pointing back to the newsletter, and then having the opportunity to invite folks who want to get engaged with other ways that I can support them, whether that's coaching or a course. And then I'm thinking next year about live events. The HERO hour or something that I'm launching, [HERO stands for the Head of RevOps]. Then maybe playing with the idea of small mini workshops, like you mentioned earlier. So there's one piece in my courses that folks gravitate towards ... We could probably do a breakout two to three-hour session deep on one specific topic. It's like a lab, and then hopefully folks can show results after that."

I referenced his process for creating a newsletter and asked if he gets writer's block for the in-depth essays every week.

Jeff said yes, those newsletters are about 2000 words, which is pretty big compared to LinkedIn posts which take him five minutes. He'll reference past LinkedIn posts for newsletter idea content to expand on, or questions someone's asking him recently, or something he's currently working on in his full-time job. "So there's some self serving to some of the articles I write because I happen to be working on that one topic at work as well. And so to be able to come in with a sharp edge, I start deeply thinking about writing on Sunday. That way when I roll into work on Monday, I already have at least a couple of perspectives and think through," he said.

I asked if he ever writes a LinkedIn post in advance to test out if people want a whole article on this topic.

He said no, he never writes with that intention. "I'm making coffee in the morning. My daughter is getting ready for school. I have about five minutes [of quiet] ... I just start hammering out a post really quick and then I start editing it for maybe a minute later. I'm not gonna spellcheck it, but I just throw it out there. So you'll see a lot of my posts have grammatical errors or spelling errors, because I've just shipped it super fast. Then maybe about 20 minutes will go by, I'll go back into LinkedIn and edit the page. So the folks who actually see the post in the first 20 minutes [its] real raw. I try not to overthink it. If you're gonna try to post on LinkedIn, don't overkill. I just spent five minutes or less because I think it can be a major time suck for people to endlessly spend time on LinkedIn," he said. 

What type of career advice would you give to your younger self?

Don't expect to be in the same career your whole life. Even though that's what everyone tells you in high school and college, that you have to choose one thing to do for the next 40 years. But that's not true.

So don't put so much pressure on yourself to advance in that first job super fast. Don't feel ashamed about what seems like maybe your lack of progress or lack of climbing the ladder. Enjoy the journey more. It's just not going to look how you expected it. And that's okay.

Jeff agrees, having three careers so far.

Resources we mentioned:


Additional notes from my prep work:

I had a lot more questions for Jeff prepared in case the conversation went those directions, but I deleted most of those questions below to attempt to shorten this.

Now it's your turn to share your knowledge! To the audience

Related to this conversation about Jeff and I sharing knowledge and resources about operations, whether it is through newsletters, courses, podcasts, blogs, LinkedIn posts, or other formats -- I want to encourage everyone reading this to share your knowledge in whatever format you feel comfortable with, in order to help other people.

This type of work, operations, is rarely discussed since we’re used to being behind-the-scenes problem solvers and not “bragging” about ourselves.

Please help make the answers to common operations problems searchable/findable, so other ops professionals don't have to recreate the wheel in their work.

What was your first professional community involvement? 

I think my start in official involvement in communities was before COVID, for an organization called Ellevate Network, which had a mission of advancing women in business and leadership roles. It had local chapters that held education events in person. It was during the time I was changing careers by getting an MBA, so I wanted to learn more about business topics.
  • My 'job' I gave myself was that I would take notes and then write blogs to share the info provided at the event. Sharing so others could learn, and so I could remember the learnings.
    • These were in-person events, so the info didn’t exist online elsewhere, only in people’s heads
    • Documenting! :) Knowledge sharing!
  • That led to a volunteer chapter marketing role
  • Then I was president of the chapter, had my first in-person speaking on a panel, and went to their New York conference
  • One learning from this community was that community/networking activity is a LONG GAME. Don’t expect immediate results.
  • It was helpful for switching careers. I got two freelance clients for marketing consulting when I was testing that work out after graduating.

I think the HubSpot community or forum was next, sort of overlapping Ellevate. I wanted to meet more people in the HubSpot world while learning about it.

  • I attended a few in-person HubSpot user groups when I worked at a PR agency job before Remotish, that is where I met my future boss Nicole, the founder of Remotish.
  • After I was working at Remotish, I thought being active in the HubSpot community would help me meet people, to ask questions, sometimes I could answer questions, and help the agency get better known
  • It wasn’t my official job, but I knew it was important for myself and for the company
  • It eventually led to being in the HubSpot community champions community where we all support each other, which was really nice

The community involvement in Pavilion and ops communities was discussed above. 

At Remotish, part of the onboarding program I built also talked about the importance of joining and being active in communities. It emphasized learning and helping, and not anything 'icky' feeling like personal branding or other terms people may not be comfortable doing for the first time.

What do I like best about community?

  • I love seeing people sharing knowledge, so it’s not locked away in people’s heads, and other people don't have to recreate the wheel and start from scratch
  • Supporting each other
  • Keeping up to date with trends
  • It's especially important in a new topic or conglomeration/repackaging of topics like RevOps, where it is hard to find good info online. That is why I started research for a book long ago when I interviewed Jeff in 2020. Finding consistent, helpful info online was difficult since it was a new topic.

What is your process or method for making time to interact in communities?

  • My advice is usually to set up personal systems like recurring tasks, or calendar blocking for it daily, making it a routine or habit 
  • I have a routine and time on my calendar blocked in the morning 
  • I check the communities in the morning when I arrive at the computer and my brain isn't ready for deep work yet
  • I just go down the left sidebar of Slack workspaces to check out what’s going on that day, and see if there is anything I can learn from or help with
  • This routine does mean if the community does not have a Slack workspace, then I probably won't be super involved. Unless the non-Slack community has email notifications or something to get in front of me where i already am spending time. I am not going to log into a different software or site daily since I am already doing too many things at once!

Upcoming courses

I plan to repeat that formula from my last course, of live multi-session course, live workshops, then on-demand courses, for different topics related to what I call human-centered operations, which is focused on people and processes, not tech or particular software. 

I was thinking about: what can you build once you have a reliable culture of documentation? 

  • At Remotish, I built an onboarding program and the documentation played a huge part in creating the program, running it, teaching and training the new team members, and more
  • That is actually what got me interested in creating courses, making thateducation and training program 
  • I'll be building courses about building employee onboarding programs next

Why and how I got started making courses

  • See above for the employee onboarding program that inspired the interest
  • Then I got a certification in Instructional design in August 2022
  • I volunteered to assist with one of HubSpot’s sales bootcamps in summer 2022, so I could see behind the scenes of how these courses work 
  • I signed up for a course-building accelerator for a live cohort course platform called Maven in Falll 2022, which was a new company. They targeted me with marketing well, kudos to them, good job with your marketing!
  • I decided to make a real course and not just learn about courses, so I needed a topic for that accelerator
  • For the previous year or so, I had some speaking gigs, blogs, and other content created about documentation 
    • I had seen there was a gap in information online. There was a little information that was findable in Google search about product documentation, how to use software products, but not process documentation
    • I remembered back when I was building and improving knowledge management at Remotish, when I couldn't find helpful info, so I started to create and share the info 
  • I thought this was a good topic for a course, and I already had some content, I was not recreating the wheel 
  • Started with sending out surveys to see the popular topics, questions, pain points, and gathering information about what would be useful to teach in a course about documentation
  • There ended up being four main topics:
    • Prioritizing it (getting started)
    • Writing it (template)
    • Systems to make sure it happens and spread out the work
    • Overcoming objections and building culture
  • First cohort was 1 year ago, December 2022, with several more since then,
    • I also repurposed the content into 2 live workshops and a recent recorded course

RevOps bootcamp

  • At the same time that I was making this documentation class, Fall 2022
  • There was an opportunity to create new bootcamps for HubSpot Academy. I think I saw it in the Slack workspace for the bootcamps i was volunteering for as a teaching assistant 
  • One of the new topics was RevOps
    • Not only was I still working at a RevOps agency
    • I was also sitting on all this research I had done for a book that I am very slow at writing, interviewing 35 RevOps experts such as Jeff, asking about what is RevOps, how to be successful in it, foundations of it, etc.
  • So I volunteered to help create this bootcamp, excited to use that research to make something to help people 
    • I had ideas from onboarding people at my agency and observing the services team with clients, for some of the topics that could be helpful to teach 
    • And ideas from many years of lurking in communities and seeing common struggles and questions, seeing what topics would be helpful
    • Topics that were not being taught elsewhere
  • Bootcamps have two instructors and one or two producers (the new name for teaching assistants)
    • HubSpot prefers instructors to be HubSpot certified trainers, so I looked through the trainer directory to see who would be a good co-creator/co-instructor to fill the gaps in my personal knowledge, skills, and experience
      • For example, I am bad at answering questions off the top of my head, which is why I over-prepare for  podcasts like this!
      • I am also not super technical, that is not my experience, as a people and process person
        • The combination of the words 'HubSpot' and 'RevOps' in the course name would make people assume this is a super technical hand-on building stuff in HubSpot kind of class. Which it is not, spoiler alert, but people might expect that, so I needed someone who could handle those types of questions and had that deep knowledge and experience
    • In the trainer directory, I saw Connor Jeffers, founder of a larger technical agency, Aptitude 8, and founder of an app company that was launching at the time. I had seen him doing more speaking that year, I knew he could handle questions and contribute knowledge for the course and all those things I can’t do. So I suggested HubSpot reach out to him, and he accepted
  • Dan Tyre at HubSpot was heading up the bootcamp program and we met with him every week for a few months from  October 2022 - January 2023. Dan made sure we were on track with curriculum development.
  • I was surprised that we, the volunteer instructor team, were in charge of creating all slides and workbook templates and everything. There was no content creation help from the HubSpot team, so it was more work than expected.
    •  But it was a good experience for me since I wanted to learn how to create courses and all those materials
  • Our first cohort was in February 2023.
  • They are free for 6 weeks, one-hour sessions
  • We’ve taught it 4 times as of this recording, cohorts of 150-300 people, and have gotten good feedback on it
      • Curriculum:
        • Revop Basics 
        • Current state process mapping
        • Future state process mapping 
        • Prioritizing projects, impact/effort/change management analysis
        • Making their roadmap, getting buy-in, proving success, learning to say no to requests, strategic vs tactical conversations 
        • Skills to develop and how to hire
      • Each session topic and homework build on each other, so the class members end up with their roadmap and chart of skills to train or hire for.
        • Breaking it into manageable steps each week, to gain foundational knowledge about how to be successful in a variety of RevOps roles 
      • We had to keep the content fairly general because of such a wide audience of different levels/experiences/backgrounds taking it
        • Especially the first cohort of about 300 people since so many HubSpot agencies were shifting to RevOps and it was a hot topic 
      • It was a lot of pressure to fit so much into one-hour sessions, in the designated bootcamp format and structure
  • Free classes like this are good to make it accessible for a lot of people to learn these topics
    • The downside is instructors or creators are not paid aside from an Inbound conference ticket 
    • If I ever finish that very slow RevOps book, those two efforts will tie together nicely
    • In the meantime, I get to help people be more successful in their careers while I learn about good course/training creation and facilitation 

What do I like about creating courses?

  • Helping people at a larger scale than I can help internally at one company
    • Especially since ops information is harder to find online compared to topics like sales, marketing, etc. 
  • Helping people not have to start lots of projects and programs from scratch like I did 
    • Which always annoyed me since it was like 2019, 2020, and I knew I wasn't the first person in the world to create a knowledge base or make an onboarding program
    •  But the info was not findable online. Either not shared or not great SEO
      • I've been working on improving my SEO so people can more easily find these hopefully helpful resources
  • I also have a course creation goal of making income since my company is my full-time job. Not sure I would say I 'like' that part though, selling. :) I'm hoping to improve my marketing enough to do all the selling for me! 


  • Jeff has a lot more subscribers, 2100! Compared to my 300 at the time of recording
  • Jeff started in 2020, mine started in late 2022
  • We have different formats
    • Jeff has essays of deep expertise
    • My main newsletter, let's call it the big newsletter, is curated resources of links to educational posts, articles, and other resources I saw that week in operations, leadership, and learning topics
      • I sort of have 3 newsletters, but let's just talk about the big one that is on Substack
      • Curating and sharing resources is easier for me 
      • Less pressure to have brilliant ideas every week
      • Since I am doing a wide variety of things each day as a one-person business, I am not sure I would have valuable topics I could write long-form newsletters on each week like Jeff's amazing content. 

How did you decide on the format?

  • I started my big newsletter as a way to share the reading I was already doing each week
    • I wanted to see if other people would find that useful since I was already spending time doing that reading 
    • I sign up for every newsletter in the world, which I know other people do not, it is not normal behavior. So other people may not have seen the links I am sharing 
  • I also knew I needed to start an email list for my business
    • I had a super specific list for the documentation class waitlist 
    • I didn’t want to have a newsletter be narrowly focused on documentation at the beginning, almost a year ago, because I would be building courses and other products about other operations or training-related topics, 
      I needed something more general for a main list to spin into more niche, segmented lists 
  • That big newsletter was also a test to test platforms and formats for a future paid subscription newsletter


  • The big newsletter takes about 6 hours
    • 3-4 of those hours are cleaning my inbox, reading the articles, reading the saved LinkedIn posts... time I'd spend even if I wasn't sharing it all in a newsletter 
    • 2 hours of formatting for the newsletter, writing the intro, testing links, and posting about it 
  • I have a giant Google doc I throw information into as I clean out my inbox and LinkedIn saved posts, during two time blocks on the weekend 
    • It is a running document with the latest edition on the top
    • I tried doing all the drafting in Substack, for efficiency, then they lost a draft after a few hours into it…so I went back to the trusty old Google doc
  • I have a big backlog of podcast episodes and books to feature, since podcasts and videos take a lot of time to consume and I only feature one book a week
  • I am working on making this more efficient by unsubscribing to emails I haven't found anything relevant for lately, not saving as many LinkedIn posts, being pickier about the saved input to sort through
    • I also do two rounds of editing and usually delete a few items:
      • When moving from Google doc into Substack
      • When checking links and names after I email myself a test version

My other newsletters

Documentation interest list

  • Instead of trying to keep track of  100 funnels related to my courses and their variable start dates, I thought a weekly email could be easier at least as a consistent first step
  • I feature the top 3 resources for documentation that week
    • One free resource from me, such as the latest blog
    • One link from my big newsletter, there is usually at least one about documentation
    •  One of my paid products
  • It's an easy regular cadence of information, people know what and when to expect it
  • It takes me about 15 minutes 
  • That weekly email choice vs 100 funnels for different course products was also because the email automation in the Maven platform for the live courses course was not great. They were hard to control or turn on and off depending on when a new class was starting, and having multiple classes got confusing to make sure the same people weren't overloaded with emails at the same time. My HubSpot starter plan workflows can't do normal funnel emails to contacts, it has to be automated inside form automation or inside one email that is manually sent first.

Book newsletter

  • I also have a book newsletter that is not really newsletter, but it is releasing bits and pieces of the draft 
  • It is partially to hold myself accountable for working on the book, and partially to generate interest if I ever finish it!!
  • It helps capture some emails of RevOps bootcamp attendees while I had their attention, that is a super long game strategy 
  • I discovered recently some of my procrastination is also due to starting with quotes/interviews as research, which is much different than my usual writing process. I found this out when creating the blogs where I ask for contributor quotes, those are really hard for me to piece them together to be cohesive. They are also less enjoyable to work on, it takes more work to push through it and finish... though I know it is valuable for people to read! And I like sharing other people’s expertise, too.


I noticed Jeff has many different efforts with different names, and had some questions prepared about naming.

I just use my own name because:

  • I am bad at naming, I put too much pressure on myself 
  • It's hard to categorize what I do in a clear and SEO-friendly way, as a generalist
  • Trying to think of a name I could use for everything I do is difficult. I am doing too many things!
  • It's not very creative to use my name, it probably looks like I think I'm the most awesome person ever, that I just put my name and that one picture all over everything – this is not true, I just can't think of or commit to one name 
  • I did think of a good name for the newsletter... but I found the name was already in use by someone else :(
  • Even though my newsletter name and generic subject line of 'Weekly newsletter # (weeks it's been running)' are super boring, somehow it still has a high open rate, which goes against all email marketing advice. But it's working well, so I'm not sure I’ll change the subject line for a while

Testing everything, releasing beta versions

  • For my previous business, in photography, I had a name and entire brand -- logo, style guide, and fancy website that I worked on for about a year before I tried to sell anything 
  • I came from a graphic design and photography background, so I could make everything look super established and professional, like I knew what I was doing in my business. When I knew what I was doing for the work, the craft, but not the business. 
    • That was my first business. I had an art degree, and I didn't know anyone who had their own business before I started getting involved in the photography world and learning about photography businesses. 
  • Even though I had a name and logo and branding and everything right away, that business never ended up making much of a profit after 5-6 years, when I closed it
  • So I am taking the opposite approach for this business, probably too much to the extreme
    • Beta testing rough drafts of everything I make, making it public, getting feedback
    • Not getting hung up on naming, treating it as version 1 name, prototype names
    • Which seemed like a good idea, getting user feedback on building what customers want
      • I was making $1-2k a month the first few months, which was very promising and probably more than I ever made in the photography business 
      • But the revenue fell off a cliff around April 2023 for a variety of reasons, including mass industry layoffs 
      • Hopefully, the new year will bring new budgets for learning and development for potential customers, and more people seeking educational content to meet their New Year's goals. I've working hard to improve my marketing in the meantime, to be easier to find and easier to purchase.

2024 plans (prepared since we recorded in December)

  • One resolution or goal the past few years was to try to have fewer yearly goals, to manage expectations better. I don't think I succeeded!
  • Two sort-of personal goals, but my personal and business life are really connected:
    • Finish book the first 6 months of the year
    • Start instructional design master's degree second half of the year
      • I get a big discount on tuition because I work part-time grading papers for a university, so that degree is the long-range plan 
      • The degree is competency-based and at a nonprofit, so it is affordable and I can go as fast or slow as needed 
  • Business goals
    • Continue documentation courses and content
    • Continue RevOps bootcamp at least until after the book is out for a while
    • Make a referral/affiliate program
      • I made an award-winning referral program for Remotish, earning a majority of the revenue. That makes me procrastinate this project, putting too much pressure on myself…also different types of business, services vs product business
    • Create a course and products about building employee onboarding programs
    • Financial goal is the same as last year's goal I didn't accomplish -- to make enough profit in my business to cover my living expenses, which may be more realistic for the second full year in business

Topics:   Documentation, Event