Follow me for tips on how to buy software companies and run them 100% remote. 6x founder, acquired 13 software companies, CEO of Ionic Partners

Joined May 2009
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I've been CEO of 20 companies and have managed dozens of VP/GMs. Here are 4 of the most common mistakes I see when these senior leaders set annual goals:
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19 Jan 2025
100% agree…. Furthermore - there will a AI disrupted enterprise software and AI enhanced. Investors need a strong point of view of each category.
18 Jan 2025
Driven by AI, we are entering a new era of enterprise software, ushering in systems of intelligence.  In the mid 1980s, driven by the growth of the client/server architecture, we saw the dramatic rise of systems of record. These are the back office software applications that helped enterprises run their ERP, HR, CRM, and core IT workflows. These technologies were relatively specialized, and helped automate any of the most critical tasks in the enterprise. They were defined by structured data, back office automation, and leveraged by only by select users in an enterprise. With the rise of cloud and mobile in the mid 2000s, we saw a new era of systems of engagement, as coined by Geoffrey Moore. In a world of much more dynamic and ad-hoc work in the enterprise, systems of engagement were tools for collaboration, communication, video, work and project management, social and intranets, and more. These tools dealt with all the messy, unstructured data in an enterprise - the conversations, collaborative docs, and media that began to drive a shift in how the entire enterprise worked.  Now, in the mid 2020s, we are firmly entering a new era of enterprise software, which gives rise to systems of intelligence. Systems of intelligence combine enterprise data, workflows, and AI, to deliver insights and automation to an organization. Importantly, because of the ability for AI to process unlimited unstructured data - like documents, video, or communications - we also get the same benefit from this messy data as we did our structured data. We can query, synthesize, calculate, and automate all the work around thus unstructured data just as easily as we could query a database before. Unlike systems of engagement that generally broke down the more information that goes into them, we see the reverse now with AI, where software can become more powerful and useful the more data it has access to. And with AI Agents being a native property of systems of intelligence, these systems aren’t only leveraged by every employee, they dramatically expand the output of the workforce. Systems of record are where people work by largely themselves. Systems of engagement let users work collaboratively with other people. Now systems of intelligence let us work seamlessly with people and AI.  These systems will also talk to each other in completely new ways. Instead of deterministic APIs and clear handshakes, with Agentic AI, these systems will communicate with each other much like a humans do. A user will make a request in one system, and it will fan out the ask to a variety of other similar systems relevant for the desired information. And if it didn’t get what it wanted, it will simply request again in a different way, just as a person would. We’re going to see systems of intelligence in every domain of work - across every line of business and every vertical. Some of these technologies will be incumbents that evolve, and many offerings will be brand new startups that fill a new gap between existing systems. Wild times ahead.
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As a CEO - the end of year is always a critical time to have your senior leaders spend time reflecting on what worked and didn’t - and setting the vision for the upcoming year. Here are the 2 long form docs I always have my teams write (and I assess their capabilities with):
11 Jan 2023
I currently manage 14 VPs of various divisions within 3 companies. These are the 2 most important documents they produce all year (with templates):
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22 Oct 2024
If you can teach your kids 1 thing - make it confidence…
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16 Oct 2024
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22 Aug 2024
This coaching is applicable for all managers
Holding team members accountable is simultaneously one of the hardest and most important things to do in business. Here's how to do it in 3 easy steps:
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19 Jul 2024
Amazing visual…
12-hour timelapse of American Airlines, Delta, and United plane traffic after what was likely the biggest IT outage in history forced a nationwide ground stop of the three airlines.
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Andy Tryba retweeted
In 2 pages @JeffBezos teaches you more about high standards than you'll learn from reading 2 books. The art of summarising that which resists summary is critical to achieving greatness. The world will forget you, except what you've written down, then what you've written down well
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Great example of understanding something at the atomic level - then making decisions on it. All managers have something to learn from this answer.
7 Jun 2024
If you want a detailed explanation of why I switched Starship from carbon fiber to stainless steel
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16 Apr 2024
Nothing brings me more joy than unteaching my 13-year-old common core math…
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26 Mar 2024
We were honored to the humble stewards of @rogerdickey & @dolaoseb amazing @trygigster vision for 2.5yrs under @IonicPartners. Thank you & I hope we helped advance the cloud vision... Ionic Partners Completes Sale of Gigster to Virtasant einpresswire.com/article/697… via @ein_news
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26 Mar 2024
Honored to ‘be’ the humble stewards…. Sorry for the typo :)
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25 Mar 2024
After 46 years - I finally did the math. I was actually born a day earlier due to timezones. Curious debate - should birthdays be celebrated based on the calendar day or the exact moment we entered the world (considering where we were born)?
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11 Jan 2024
301 Reshaping Leadership for the Remote Revolution: AI Integration, Motivating Dispersed Teams, and Scaling Through Change with Veteran Tech CEO Andy Tryba | Partnering Leadership Global Thought Leader partneringleadership.com/301…
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Teaching your kids to set annual goals is a life skill that will change their lives forever. I’ve tried various methods over the years and continually failed. Until I finally cracked the code. Here is what I painfully learned:
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6). Post on the fridge - and keep the goals visible throughout the year. Use family dinners to ask about how they are going. Celebrate any incremental accomplishment.
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7). Don’t try to force them to accomplish - they will do the goals that they’re passionate about. This exercise is more about them learning how to set annual goals than tiger-dad execution management. Best if they drive accomplishment on their own.
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