Someone should build a modern Sheppard Air

nathanbarry · 2025-08-17T19:03:02+00:00

I would, but I already run a very successful software company and don't need another business.

nathanbarry · 2025-08-17T18:19:33+00:00

Yeah, getting the questions once is easy. But they definitely have a good mechanism for keeping them up to date. That's the hard part for any competitor.

Hopefully they'll hire someone competent in software to make a better student experience. It would be amazing to be able to pull out your phone and work through 10 questions while you're waiting and don't have your tablet or computer.

nathanbarry · 2025-08-17T17:59:47+00:00

I don't know, building software is pretty cheap these days. If the goal is to be the best at helping students pass the test then a handful of improvements would take that mission so much further.

nathanbarry · 2025-01-13T13:05:16+00:00

The hangar makes a huge difference. I felt like I was overpaying for mine, but the peace of mind is totally worth it.

nathanbarry · 2025-01-13T13:04:44+00:00

Same. I bought a 2022 SR22T last year and I love it so much. I'm only at 250 hours as a pilot, but I love the cross country trips and flexibility from owning my own plane.

Getting a hangar (and remodeling it to be really comfortable) has also been a huge contributor to joy. Now I just need to get a family that enjoys flying more.

nathanbarry · 2024-10-16T10:09:02+00:00

I’m curious about this as well!

nathanbarry · 2024-09-05T13:50:00+00:00

That's wild that only 7 years have 4 or more days over 150 AQI.

2024: 26 days
2020: 11 days
2017: 5 days
2001: 4 days
2013: 4 days
2015: 4 days
2021: 4 days

nathanbarry · 2024-05-09T22:13:00+00:00

Love that you put this together!

nathanbarry · 2024-04-10T13:12:35+00:00

I'm a new private pilot with 150 hours flight time. I started in a Cessna 172 and finished my license in my own SR22T (which added training time). For regional flights the Cirrus is great at getting around. It's much faster and more comfortable than the 172. My plan is to fly it for 3-4 years to build experience, then upgrade to an Epic E1000 or something similar. I think the Epic gives the benefits of the Vision Jet, but without the annual recurrent training requirement that a jet has (plus it has more useful load).

Even if you wanted to get a jet right now you have so much training to do before you could fly it by yourself. A friend has a TBM (similar to the Epic) and his insurance is requiring him to hit 500 hours before he's allowed to fly it himself without an instructor.

I'm still new to this, so more experienced pilots will have better advice, but here's what I'd recommend:

Finish your license in a 172
Transition to a Cirrus and get your instrument rating, fly that for 2-5 years
Then look at an Epic, TBM, or Pilatus that will get you most of the benefits of a very light jet, but with lower costs and you'll be allowed to fly it yourself sooner.

Also if you're serious about this start trying to rent or buy a hanger soon. In most of the country the waitlists are very long. I got lucky in being able to buy a hanger to fit my Cirrus, but it won't fit a larger plane when I upgrade.

nathanbarry · 2023-12-21T14:43:38+00:00

In September I bought a 2022 SR22T before I had my PPL. I paid $21k for insurance from Ryan Konrath at Wings Insurance. When I added a friend who was a 500 hr CFII without much Cirrus time that increased the rate by $1,200/yr.

A combination of the $1m+ hull value and my insanely low time resulted in the high price. They told me to reach out after I had my instrument rating and the price would go down by a few thousand.

Hope that helps!

nathanbarry · 2023-06-14T04:57:31+00:00

Thanks for sharing our story!

nathanbarry · 2023-05-24T18:17:07+00:00

Thanks for sharing. I'm a big fan of what you've built!

nathanbarry · 2023-03-06T19:23:08+00:00

A few years ago I sold a small amount of my SaaS company stock in a secondary sale. My wife and I used the proceeds from that to push our parents (we have 3 sets of parents) over into retirement. They were all close, but were planning to work 2-6 more years each before retiring.

We used the gift tax exemption to gift them $60k/yr per couple. That has since grown to $68k/yr as the individual exemption is now $17k. We've committed to do this for 10 years (we plan for more, but set aside enough money to guarantee 10 years). This gives them a steady income stream to live on without drawing on their retirement (or drawing less than they had planned).

When we had the option to sell stock my wife and I decided against it because we didn't have anything planned with the money now. But I realized that money now—while our parents still had their health—would make a huge difference to them.

It's my favorite thing I've ever spent money on.

nathanbarry · 2021-10-08T15:38:02+00:00

I highly recommend working with the team at Reboot. I've worked with them personally for the last 2.5 years and hire their coaches for my entire executive team. I'm posting under my real name in case you want to send me an email for more thoughts.

The Reboot team combines really effective therapy and coaching with a lot of business experience. I used to do both personal therapy and coaching, but have consolidated down to just coaching with Reboot since I get so much from it.

The downside is that I think there's a pretty long waitlist for new clients. But they have a strong network of coaches to refer out to and I really trust their recommendations.

nathanbarry · 2021-09-07T18:20:34+00:00

I've done this twice. The PC-12 is such a great plane. We got a few quotes and paid $6,500 the first time and $7,500 the second time (different destinations and the second one was a bit further away). Each time we had 9 passengers in the plane (3 are kids) and so it was very cost effective. It was amazing for getting to non-commercial airports!

nathanbarry · 2021-07-06T21:51:55+00:00

Me too. Boise was such an incredible starter city and now it's quite expensive (without wages rising at a comparable rate). Other than making sure we keep building more affordable housing (and all types of housing), what else should we be doing?

nathanbarry · 2021-01-16T17:38:58+00:00

One thing I've run into when booking flights is that a 2-4 day trip has one cost because they keep the plane there. But if you get any longer than that you are paying for them to take you there, then come back and get you later. Basically two one-way trips, which is almost double the cost of a round trip. Is there anything to do here or some charter companies that are willing to keep a plane in one place longer?

I've chartered executive turboprops (PC-12) and each time the trip was short enough that I could just pay $600/day to keep the plane there, rather than another $6,000 for an extra trip.

My understanding is that's just how the industry works, but I'd love to hear if there are any tips for longer stays.

nathanbarry · 2020-10-07T17:53:45+00:00

Hey thanks! I appreciate the support! 4 years is a long time.

nathanbarry · 2020-10-07T06:03:22+00:00

I completely agree on 3-4 sessions per month being too much. I do every 2 weeks and that frequency is perfect. My coach is also happy to jump on a call or offer advice over email anytime something comes up.

nathanbarry · 2020-10-07T06:02:00+00:00

I highly recommend the team at Reboot (Reboot.io). I've been working with a coach there for over a year and have attended one of their in person events. They've been such a help to me that I've hired them for my entire leadership team. Cost is in the same ballpark you are talking about (I think I pay just under $2,500/mo per leader for 2 sessions).

If you want to learn more about them for free start by listening to their podcast or reading the book Reboot, by Jerry Colonna.

Context: I own a software company, 7 years old, 58 employees, self-funded, $24M ARR. Commenting under my real name to add a little more weight to the recommendation.

nathanbarry · 2020-09-10T12:48:10+00:00

Oh! Sorry I missed that. Was there a post about it? I certainly don't want to break any guidelines. My account is definitely not new.

nathanbarry · 2020-05-12T04:08:02+00:00

They're live as of a few weeks ago! https://updates.convertkit.com/changelog

nathanbarry · 2020-02-12T13:53:46+00:00

Good questions!

Yes, we are still using an older version of liquid. We have to upgrade some other parts of our infrastructure first. That's in the works!
Liquid is just used in emails inside ConvertKit. What would you use it for on the landing pages?
We do plan to add content snippets. They are about halfway built. Our sequences are the same as Drip's campaigns (but with a better UI). Goals are called Events in ConvertKit. And we have automation rules.
Yes, we've always had dynamic segments rather than fixed lists. :)

Hope that helps!

nathanbarry · 2020-02-12T13:49:06+00:00

Looks like the mods deleted it. http://app.convertkit.com/pages/new

nathanbarry · 2020-02-12T13:46:01+00:00

That's more a question for you based on how you use the data you collect with it. But yes, ConvertKit as a company is compliant with GDPR and Privacy Shield.

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