Founder @LegUpHealth, VP of Revenue Operations @WindfallData, Podcast @StartuptoLast, Writer @ https://xitter.cf/t.co/y53wcEV9Mf

Utah, United States
Joined May 2011
So proud to be a small part of this!
🔥 Beyond excited to announce our $65 million investment from Morgan Stanley! 🔥 I'm so proud of the entire @WindfallData team and the growth that @DRS85 and I have seen over the past several years. We're thankful to our 1,500+ customers. It's been an amazing journey thus far and we can't wait for the next chapter. Let's go!!! windfall.com/company/news/wi…
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Rick Lindquist retweeted
One of the biggest questions we’re hearing from clients right now is: "How do I keep offering competitive benefits when I also need to cut costs?" It’s a valid question, especially when benefits are often the second-highest expense on the books—right behind payroll. leguphealth.com/blog/navigat…
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First personal newsletter send of 2025. Hoping to write more this year! ricklindquist.kit.com/posts/…
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Rick Lindquist retweeted
Live in Utah? We'll help you find, use, and manage your health insurance

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Have been an executive (VP level) at a high growth startup for 3 years or so. And I can assure you that it is no where near as hard as being the full-time CEO of a startup, high growth or not.
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I'm using generative AI daily now and I just keep finding more ways to use it. Pretty neat.
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I'm super grateful to work with @jdcleary and @TylerMKing on @LegUpHealth. Our monthly partner meetings are awesome and productive. It's a side project for me, so I typically don't get to spend a ton of time with both of them at the same time. JD is leading the way with daily execution, and Tyler brings a long-term perspective w.r.t. to decision-making that we couldn't replicate without him.
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It is so hard to tell the difference here. I can relate to the OKR/Google example. Wouldn't it be nice if implementing a goal framework automatically made your company or team better?
A company can succeed 𝘥𝘦𝘴𝘱𝘪𝘵𝘦 its processes, not 𝘣𝘦𝘤𝘢𝘶𝘴𝘦 of them. How do you know which is which, in some organization you’re wanting to copy (e.g. Google’s OKRs)?
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June was a record month for @LegUpHealth in terms of MRR, operating profit, and bookings. And it's outside of open enrollment! @jdcleary is crushing it!
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Plug: @LegUpHealth is a health insurance concierge service that provides unbiased guidance and year-round support to Utah small businesses and their employees to give them confidence they’re enrolled in the right plan for their budget and needs. LegUp Health supports all available small business health benefits approaches (group, individual, and hybrid) in Utah with all health insurance companies (SelectHealth, Aetna, Regence, etc.) Don't wait until open enrollment to start saving time + money and also gaining peace of mind with a better health insurance experience. Make us your agent today! See leguphealth.com for more information.
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My favorite episodes are the ones Tyler and I forget we are recording and just laugh and talk about random stuff. I'm not sure if it's good radio when it happens, but it is fun.
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If someone wanted to lease a Cybertruck for business purposes, what’s the best way to make that happen?
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Exceeding expectations isn't just about getting stuff done. It's also about managing those expectations.
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I have a few internships available for aspiring sales professionals in Utah. Any advice on how to attract candidates?
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Learnings so far: - There are people at Universities and Colleges whose job it is to find people interns => find these people - Create a posting that's easy for people to share with a super clear WIIFM => keep it simple
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If you're interested in the oral history of Utah's entrepreneurial tech ecosystem, check out The 4th Node podcast. @NicoDato and @adamedmunds do a fantastic job extracting historical context from all angles (investors, entrepreneurs, academics, operators, etc.)! 4thnodepod.com/
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I’m feeling grateful for this podcast right now. It provides context on the Utah technology ecosystem I am missing. It also reminds me of the people who have helped me directly (e.g. past investors) and continue to help me indirectly (anyone who contributes to growing the Utah ecosystem). Several individuals have had outsized impact, and I think it’s cool a way to recognize them and learn from their stories.
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I tend to agree with just about everything @morganhousel says. This episode with @shaneparrish is worth a listen if you're interested in developing simple ways to understand how you and others think about money. I'll *try* to get some notes on soon. fs.blog/knowledge-project-po…
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