Category: Newsletter (Page 3 of 23)

I took part in a group discussion Monday evening. The starting point was a utopian blog post about the future of AI. That blog post is titled “The Gentle Singularity.” It paints a rosy picture of a future like what was once portrayed on The Jetsons, only better. It is a picture that OpenAI needs to keep before the public for its own interest, a picture that I cannot see. Read for yourself if you want to read the AI maximalist perspective. There have been rejoinders from others working to build AI technologies that I find more compelling. But even more, I thought about the older, deeper insight expressed by Dostoyevsky in Notes from the Underground

Shower upon him every earthly blessing, drown him in a sea of happiness, give him economic prosperity such that he should have nothing else to do but sleep, eat cakes and busy himself with the continuation of the species, and even then, out of sheer ingratitude, sheer spite, man would play you some nasty trick. He would even risk his cakes and would deliberately desire the most destructive nonsense, the most uneconomical absurdity, simply to have the right to his own fantastic desires!

That is a much easier thing to imagine. As I sometimes say, with the grammar deliberately incorrect, people is people. I don’t see that changing any time soon.

As for the conversation itself, there was a wide dispersion in the room as to how much people interact with AI tools. I’m hardly a wizard and haven’t tried to vibe code anything yet, but I do keep multiple windows open to converse with large language models and we’ve built simple agents to streamline repetitive workflows. That put me around the bottom of the top quartile in terms of use. I like to hear how people use the tools. I might not be able to use them in the same manner, but hearing ideas from people in other fields is often the source of the greatest insights. I didn’t come away with any breakthroughs, but the conversation did get my mind turning on a few ideas.

I took part in a group discussion Monday evening. The starting point was a utopian blog post about the future of AI. That blog post is titled “The Gentle Singularity.” It paints a rosy picture of a future like what was once portrayed on The Jetsons, only better. It is a picture that OpenAI needs to keep before the public for its own interest, a picture that I cannot see. Read for yourself if you want to read the AI maximalist perspective. There have been rejoinders from others working to build AI technologies that I find more compelling. But even more, I thought about the older, deeper insight expressed by Dostoyevsky in Notes from the Underground—

“Shower upon him every earthly blessing, drown him in a sea of happiness, give him economic prosperity such that he should have nothing else to do but sleep, eat cakes and busy himself with the continuation of the species, and even then, out of sheer ingratitude, sheer spite, man would play you some nasty trick. He would even risk his cakes and would deliberately desire the most destructive nonsense, the most uneconomical absurdity, simply to have the right to his own fantastic desires!”

That is a much easier thing to imagine. As I sometimes say, with the grammar deliberately incorrect, people is people. I don’t see that changing any time soon.

As for the conversation itself, there was a wide dispersion in the room as to how much people interact with AI tools. I’m hardly a wizard and haven’t tried to vibe code anything yet, but I do keep multiple windows open to converse with large language models and we’ve built simple agents to streamline repetitive workflows. That put me around the bottom of the top quartile in terms of use. I like to hear how people use the tools. I might not be able to use them in the same manner, but hearing ideas from people in other fields is often the source of the greatest insights. I didn’t come away with any breakthroughs, but the conversation did get my mind turning on a few ideas.

Last night, I watched the final episode of the first season of Department Q. Netflix suggested it to me when it was released and I was looking for a new show so I gave the first episode a try. Besides, I was curious what might set the subgenre Tartan Noir (the actual description Netflix provides) apart. Then I proceeded to watch all nine episodes in the space of about two weeks.

As might be guessed, the show is set in Scotland and features some dark and violent themes. The novels on which the show is based are set in Denmark I’ve since discovered but Netflix decided to place the show in Scotland—similar climate but less need for subtitles. From the outset there is violence as the show begins with the main character, a detective, returning to work after being shot in the line of duty complete with flashbacks. Skirting rules in order to get him back to work, the detective’s superiors place him in charge of his own new department to work on cold cases. Mind you the department occupies the basement of the police building and the main character is not thrilled by this development, but it suits his own inner turmoil and outward abrasiveness. The department starts as only Detective Morck, but he is shortly joined by others battling their own inner struggles and they form quite a team of misfits.

They choose to investigate the disappearance of a prosecutor from several years prior, a young woman who vanished from a ferry shortly after a murder suspect she was trying was acquitted. I won’t offer a plot synopsis because I don’t like reading those. What I will say is that the characters have real depth, and with the length of a TV series there is enough time for the plot to breathe so that the characters are able to evolve and develop. The violence is never gratuitous but the show doesn’t shy away from the darkness either. There are moments of levity interspersed throughout, too, but what starts as a slow burn doesn’t end that way. There are also a number of subplots that arise as the investigation unfolds, each with its own set of characters and motivations and none of which distract from the overall experience.

In advance of today’s self-funded search event, the organizer hosted a dinner for all of the speakers and sponsors. Since the event is in the financial district and he is a foodie, he picked a Peking duck restaurant in Chinatown. It was one of those restaurants with such a literal, on-the-nose name that you know it is the real deal, complete with a large flag overhanging the sidewalk with a duck on it, and it did not disappoint.

The first time I experienced Peking duck I was in Peking, or Beijing as we now call it. It was a trip during a January term in college. There, they kept bringing out more duck and more beer and more duck and more beer. Before the meal ended one of the chaperones fell out of his chair, and it wasn’t from eating too much. That incident and how much I enjoyed the duck were the two standout memories of that evening though I have many other fond and not-so-fond memories of that crazy trip.

In comparison, this was a much tamer affair. No one had more than a drink or two, people discussed business topics and swapped industry war stories rather than what a group of college students might discuss, and there were other dishes on the family-style table for those who didn’t like the idea of eating the roasted duck. The duck itself was very good, though in fairness none of the times I’ve had Peking duck has ever lived up to my memory of the first time I ate it.

I capped off my evening with a cup of strawberry lychee ice cream. It isn’t a normal combination as lychees are native to Asia, but as I was in Chinatown in NYC it was available. Both flavors were mildly sweet and the ice cream was more an amalgam than an even mixture of the flavors. It wasn’t as layered as some ice cream I had on a Marrakech rooftop at the start of the year (that one also had a citrus bite that I like on the odd occasion when I don’t stick to vanilla), but it made the walk back to my hotel more pleasant.

This week marked our fifth and sixth M&A conferences of 2025. We made the decision last year to commit to the conference circuit this year and we’ve implemented that plan. We won’t repeat the initiative in 2026. Working a conference floor hardly plays to my strengths, the travel makes regular work more challenging, and I risk travel burnout going to places I probably wouldn’t otherwise visit. Relevant to our current trip, I’m hardly a Disney adult or a theme park junkie.

Each conference is a bet, a wager that the time and money spent will generate a positive return. While for some of the conferences it is still too early to perform a final accounting, for others we knew immediately. This is all part of the iterative process of building a business. With each attempt, our aim ideally improves. There was a time, after all, when we went to startup and SaaS conferences even as we were leaning more into M&A work. At least these events had actual prospective clients and partners attending.

Conferences aren’t the only bets we’ve made this year, but they have taken up more time than the others. And since we track prospect sourcing, we know what’s working and what isn’t. Knowing what we knew at the time, each of the bets was justified. They just won’t be repeated. Making small bets is essential in building a growing business. It’s also essential to stay nimble by not doubling down on things that aren’t working to focus on the things that are. With the knowledge we’ve gleaned from the conference circuit, we have a different plan for our upcoming bets. Those bets probably won’t be the final version of business development either, but they should be slightly better than our prior efforts. It’s not a flashy process. It’s not a sexy process. But it has worked and it will keep working.

One of the conversations I had after last week’s event in Philadelphia has me revisiting a book I read in part earlier in the year and that has been sitting on the table beside my recliner in the months since. The book was first recommended to me by one of our referral partners who is building a well-oiled business machine. That was sufficient justification to buy Buy Back Your Time and skim through it searching for ideas. I’ve implemented a few of the basic concepts already and have looked over the mental frameworks a few times, but we’re about to embark on a real quest using the book’s framework as version one of a new trial. The goal over the coming months is to tackle that most insidious of modern time sucks, the email inbox.

The email inbox can be problematic in many ways. My biggest problem is not that I’m drowning in volume. We’ve implemented some routing flows that have addressed that issue and it’s not like I was getting hundreds of emails per day even before that. My biggest problem with email is that I have it open almost all the time, a residue from a past life.

When I worked for a big law firm, I grew to fear email. We had to be on all the time and if we didn’t respond within a few minutes we could face quite the hiding from our bosses. One of my good friends even developed muscle spasms in his leg from the anxiety of waiting for the next vibration notifying him that another work email arrived. When people ask me why I left the big firm, that little vignette is one of the anecdotes I tell. Despite all of that, immediate responsiveness was so deeply engrained that it is still a mental battle. And this even knowing the benefits that await on the metaphorical other side and after having turned off email phone notifications.

Has anyone gone through the steps outlined in the book, email-related or otherwise? If so, feel free to let me know which parts have worked well for you, what you might have tweaked, and if anything didn’t work at all. I’m more interested in the first half of the book than the second currently but I appreciate in advance any thoughts or comments.

Over the past week and change, I’ve had two dinners with friends. They’ve been quite a salve during a time when I’ve needed it. The meals themselves were very different. One was at my apartment. I cooked venison, roasted cauliflower, and used my fancy new rice cooker. Since I added sour cherries to the rice, that was the hit of the evening. It was a calm meal with relaxed conversation. The other was at a new small plates restaurant aiming for a Miami feel—art deco décor, Latin food, and tropical plants. Everything was close but not quite there. They have, however, definitely nailed the way-too-loud music element that is quintessential Miami.

This morning, too, I had breakfast at Chick-fil-A with most of the group from my men’s bible study where I had a regular chicken biscuit. Even though the sessions have concluded for the spring semester, it was nice to get together with those guys as that has been one of the few consistent places where I’ve been around men who are further along the journey of life than I am. Since I own my own business and we work from our apartments, I don’t get that from work as might have happened in an alternate universe.

None of these three meals was really about the food. They were about the conversation, the jokes, and the what-did-you-just-say moments. These are the sorts of things I haven’t done enough, the sort of things I’ll need to do even more as spring turns to summer and I have more free evenings. One of the reasons I chose Durham when I came back to the Triangle was because it has better and more varied restaurants than Raleigh. I even have a spreadsheet of places that I update occasionally and share with people who want local inspiration. Maybe I’ll finally start filling in more of the rows in the notes column of that spreadsheet.

Spring is always a time of change. I felt this in many positive ways during a nice long hike on Saturday through a mix of hardwoods, loblolly pines, and prairie meadows at a nearby nature reserve that I hadn’t visited before. It was a lovely walk, the weather was great, and there weren’t many people around. My allergies even held off until the very end.

There seem to be even more transitions than I expected this spring. I knew curling was wrapping up (Monday after I played one of my best games of the season), that my morning bible study was ending, and that there would be a lot of work travel that has really only just started, but there is more. Yesterday, the SBA announced new rules governing the 7(a) program that rein in some of the flexibility that was introduced into the system last year. We’re still processing the changes, but I don’t expect the net result to be positive. I could say the same about a number of other things. These collective changes make our 2025 growth initiatives even more important and those are focused on adding different types of customers, a planned transition but on an accelerated timeline.

I’m also coming towards the end of my current lease, which is always a time that causes a little pause. Following my historical pattern, now is about the time to move somewhere else. That isn’t necessarily a pattern I intend to perpetuate, but I can’t help thinking about possibilities in ways that I wasn’t even in March. I can’t be the only one who has these sorts of thoughts every couple years.

There were lots of meetings and plenty of work at the back end of last week as we only returned from Las Vegas late on Wednesday night. It is part of the process and we’ve made things better by clustering meetings, but meeting days can turn into exhausting days quickly. This is especially true when my sleep is disjointed as a result of being between time zones.

When the normal workweek finally ended, I walked to and ate dinner at my favorite Thai spot. At this point, the waitresses definitely recognize me. I had my usual pad see ew with chicken.  Then I had mango sticky rice for dessert as a nod to the passage of time. Mango sticky rice is one of my more recent culinary discoveries, but boy oh boy is it good. I’ve even purchased sticky rice at an Asian grocery store so that I can make it at home though I cheat and buy precut mango when I do so.

After dinner, I went to a gathering at one of the many downtown taprooms that I can walk to but hardly ever visit. It was organized by my church small group as an extracurricular group activity. I wasn’t planning to attend as birthdays are something I stopped looking forward to several years ago. But I also received a text message that people from my men’s bible study were also going and I decided the social costs of no showing two groups were more than I wanted to pay. I arrived late as the restaurant was busier than I’d expected, but I’m glad I did. It was a great chance to get out of my own head and a welcome reminder that I do have a little bit of community here.

I don’t gamble in casinos. That is a decision I made several years ago and so don’t need to revisit when I walk through the casinos when I’m in Las Vegas for work, a situation that has arisen at least once per year for a few years now. It saves mental energy not to have to think about it, not that I’m attracted by the slot machines anyway with all their light and motion and noise.

I am gambling in Las Vegas this week, though. We have a limited budget of time, energy, and money for business growth. When we made our plans for the first half of 2025, DealMax was an event we circled. It marks a different path, an attempt to press more into a different client avatar and to diversify our client origination mix. That is largely the theme of the events we’ve chosen for this season as we probe different ways to evolve the business. This builds on the exploration of 2024 and hopefully will benefit from the lessons learned through those efforts.

Some of our prior initiatives have been grand slams. More have been strikeouts, with a smattering of singles and doubles and one or two I might describe as balks. With each we search for the potential of leverage or nonlinear success, the opportunity for one talk, program, or sale to result in multiple transactions or clients. This event brings together private equity funds and investment bankers in a manner that might be unreplicated elsewhere. A single success here could mean multiple transactions for us, so we made the trip.

We may not know if this gamble will pay off for six months or longer. But our growth budget is about making bets and we liked the potential asymmetry of this one. Will we approach things differently if we come back next year? Sure, but overall we’ve accomplished what we came to accomplish. Now we will win the follow up and open some of the metaphorical doors that we’ve cracked ajar.