
LegUp Health
We make health benefits simple for businesses and nonprofits
It gives me great pleasure to announce that JD Cleary has joined LegUp Health as General Manager to scale our health insurance concierge service in Utah. JD brings 10-plus years of experience helping families and small business owners navigate the complexities of health insurance. Most recently, JD was a Vice President at PeopleKeep, where he helped build a profitable business with millions in revenue.
Read more here: https://www.leguphealth.com/blog/jd-cleary-joins-legup-health-as-general-manager

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We recently crossed $2,000 in monthly recurring revenue (MRR) at LegUp Health. We have just over 100 users of which almost 40 are agency clients.
I just did my monthly model update. We're cash-flow positive for the rest of the year. That is pretty cool.
The first half of 2021 has been dedicated to creative work.
We've launched a ton of new content on the Blog and we've built out a comprehensive state guide to every individual health insurance policy available in the state of Utah.
We've also automated several manual internal processes. For example, we previously had to manually construct and send a monthly account update email to each user with details on their health insurance policies. This is now automatic thanks to a software script.
Right now, the plan is to spend May and June focused on improving the service before shifting our focus to sales and marketing (i.e. growth) in the second half of the year.

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At my last company, we built a blog that grew to hundreds of thousands of monthly visitors and that was regularly cited by top news and research firms.
I'm excited to build something even better at LegUp Health.
Health insurance is complex. As the shift to consumer-managed health insurance accelerates, Americans will need help finding, using, and managing their coverage. I want LegUp Health and this blog to be a trusted resource for all.
I hope you will consider subscribing and contributing to our discussion. If you have topic ideas or requests, please let me know.
Read more here: https://www.leguphealth.com/blog/welcome-to-the-legup-health-blog

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Nothing in life is more important than you and your family's health. But with so many health insurance salespeople out there, it's not always clear who you can trust. You deserve better.
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I plan share some learnings later this week in a separate article. Let me know if you have any questions you'd like me to cover in that post.
Last month, LegUp Health's inaugural Summer Internship Program came to an end. We "employed" (and I use this term loosely) 6 non-paid interns this summer after sifting through 30+ applications.
Our interns represented top universities including Yale, Duke, UNC, and MIT. And they were from states all over the country (U.S.). Below, I have included a picture of the interns. As you can see, it's a diverse group:
Our interns worked on projects ranging from "building a go-to-market plan" to "creating an explainer video" to "designing a client education course." Their work was valuable and will contribute directly to immediate or future efforts at LegUp Health.
If you'd like to review the program we offered, here is an overview in a Google document with links to each of roles we offered and filled. Please note that I may update this document based on learnings for next Summer. For the time being though, this is exactly what we offered and delivered on. Feel free to repurpose this for you own use or offer feedback.
One intern has become a paid team member
One intern, who is a rising Junior at Yale, decided to take a "gap year" away from college due to COVID-19. As a result, she's joined LegUp Health as it's very first paid team member. She'll be helping me ramp up LegUp Health's marketing efforts for the rest of 2020 based on her work on the go-to-market plan project during her internship.
A few learnings based on experience and feedback from the interns:
1) It was an incredibly rewarding experience. For up to 12 weeks, I met weekly with each intern to coach and mentor them through their project. The internships were self-guided, so I encouraged each intern to follow their curiosity to wherever it led them. As they progressed the project, we collaborated asynchronously (non-real-time) via Google Docs, email, and Slack. Founding a startup can be a lonely journey. I learned internships are one way to make it less so.
2) Some of the projects were too broad in scope. For a couple of interns, this meant they did not completed a "final deliverable" for the project. I learned this final deliverable is VERY important for the intern. It gives them something to show and tell their family, friends, and potential future employers. Next summer, we will ensure all internship projects result in a final deliverable for each intern.
3) We didn't maximize intern-to-intern relationship building. As a result of the weekly meetings, I was able to develop strong one-on-one relationships with each intern. However, we did not invest sufficient effort in helping to facilitate meaningful relationships between the interns. While we did do a group "show-and-tell" at the end of the program, we did not do enough early on to facilitate relationship-building. I learned that the relationships interns build with each other have the potential deliver more value than the internship project itself. Next summer, we will ensure all interns have an opportunity to develop one-on-one relationships with each of the other interns.
4) We underestimated the time offering an internship program would take. I thought it would take a few hours per week, but it ended up requiring 1-2 full work days each week of time. I learned mentoring and coaching interns take a significant amount of time. Next summer, we will consider reducing the number of interns we take on to account for this.
5) Internships are a special kind of hiring funnel. I did not expect to hire one of the interns when we offered this program. But, as you can we, we did. I learned an internship (paid or nonpaid) is a low-cost way to "test" a working relationship with someone. This can be applied year round. Going forward, I'm going to be more liberal with my consideration of short term internship projects and more conservative with consideration of long term hires.
Overall, the program was a success, and I'm glad we put the effort and energy into making it happen. I look forward to cheering our former interns on as they continue to pursue their academic and professional interests.
I'm happy to answer questions about the program or share additional learnings or details if that is helpful to one anyone.

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I put together a slide deck that goes over LegUp Health's narrative and value proposition. Here's the link: leguphealth.com/slides.
It's actually my first attempt at distilling LegUp Health into slides. I'm going to share it with the world and ask for feedback. If you have time (no pressure), take a look at it and let me know where I'm missing the mark. Or feel free to pass it along.
It's text heavy at the moment. I want to make sure I get the messaging right before we invest too much in design.

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This month, we started focusing on expanding our LegUp Health client base.
It's been a long time since I had to do cold marketing and reach out. It's definitely harder than I remember.
Our service is free of charge and takes less than 5 minutes to set up. Our early clients have been ecstatic so far. In a nutshell, we save them time and make them feel more comfortable with their current health insurance coverage. We can also help clients find new coverage, but that is not required to try the service.
Specifically, we're looking for Utah workers who buy their own health insurance. Often these are people whose professions do not provide them access to employer-provided "group" health insurance. Common examples include:
- Freelancers
- Remote employees
- Small business owners
- Startup founders
- Real estate professionals
- Dental workers
- Hair stylists
- Massage therapists
- Consultants
Getting started was hard. It took a lot of brain power and stamina to think through who to reach out to, how to reach out to them, and what to say.
By mid-month, I decided to simplified my activities by doing three things:
- Building a long list of people to reach out to upfront (and adding to it daily)
- Creating a set of templates to use for initial out reach (and iterate them daily)
- Reaching out to 5 new people from the list every weekday.
This simplification massively reduced the cognitive cost of outreach. I can get this stuff done in less than 30 minutes each day. And I can craft thoughtful messages for each of the 5 people I'm reaching out to (so no annoying spam).
Best of all, these activities are starting to snow ball. Not everyone responds to my reach out. But the ones that do, spawn many new introductions, conversations, and marketing ideas.
In July, I look forward to reaching out to 5 new people each weekday. Since there are 23 weekdays in July, I will reach out to more than 100 people by the end of next month.
Early client acquisition is a grind. I'd forgotten, but now I remember.

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It's May 27. We're now turning our attention to client acquisition.
I was hoping to be here to weeks ago, but initial product development took longer than I thought.
Since the last update, we have:
1. Launched V1 of the LegUp Health software portal. All existing clients and beta users have been onboarded. This is only V1. We'll iterate based on client feedback going forward.
2. Added text support. Clients can now text us for support at 435-XXX-XXXX. Clients can also request that we send text them our Virtual Contact Card (vCard). This makes it easy for them to add LegUp Health to their phone’s contacts and get in touch with us on the go.
3. Received our first cash from revenue in the LegUp Health bank account. I need to figure out how we can frame this and hang it on the wall. I'm open to ideas here.
4. Doubled our revenue. We went from $190 to about $380. If we can keep this up... : )
Now, we're focused on growing to 50 clients. Sometimes things take a bit longer than you expect.

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In April, we converted 6 out of our 10 beta users to actual revenue-generating clients.
This month, we'll produce our first revenue. Exciting. =)
In the first two weeks of May, we plan to wrap up initial product development on the LegUp Health platform.
By mid-May, we'll shift our focus to customer acquisition. The first milestone we are targeting is 50 clients. We plan to reach this milestone via guerrilla tactics (i.e. by any means necessary). I expect clients will come from referrals, personal network introductions, and targeted cold/warm reach out.
50 clients is significant because it will cover our monthly expenses and create a few thousand dollars in monthly profit we can invest back into marketing experiments.
From there, we can be more meticulous.

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About
LegUp Health was founded to help business owners escape the rising costs and restrictions of group health insurance. Our team pioneered alternatives that keep employees covered while saving companies money.

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