The ChooseFI guys say it all the time – it’s all about community and the genuine connections we make that help us along the path to Financial Independence.

I live in Southwest Florida, which some people call “God’s waiting room.” It’s a great place for traditional retirees, the ones that look like they have a cotton ball on top of their heads and who drive with their blinker on for 5 miles.

But it’s tough for those of us a few decades younger. I don’t really have a close-knit friend group or even loose associations with people of a similar mindset, financially. There’s a lot of the “work hard, play hard” mentality in a place where we have beautiful weather year-round and lots of people work in tourism and the service industries.

So when I got hooked on blogs like BudgetsAreSexy in 2014, something clicked in my brain. The blogger behind that site, J-Money, was the first to introduce me to the concept of maxing out your Roth IRA every year. I think his streak is now up to a decade or more! Before finding his site, I was under the misunderstanding that you could contribute to your employer plan, OR you could contribute to a Traditional or Roth IRA, but not both. At the time, I wasn’t even close to maxing out my workplace plan, let alone socking away enough for both. But it sure seemed like a good goal to try, especially since I had a negative net worth back then (read all about my horrible housing story here).

I wasn’t able to hit the $5,500 max in 2014, since I started too late in the year to come up with that much extra cash (without depleting my emergency fund). But starting in 2015 and continuing through the present, I have maxed out my Roth IRA or a combination of Roth and Traditional IRA for the past 5 years. This is a goal I have for early in the year each calendar year, because “time in the market is better than timing the market.”

Maxing out my IRA is just the start of my saving for each year, because I have grown my savings muscle to the point where I can also max out my employer-sponsored retirement plan. My 457b plan now allows $19,000 per year, up from $18,500 when I maxed it out for the first time last year. Big thanks to J-Money for putting me on a course to max out both of those accounts!

Online community

But the title of this blog post is Community, not “how Josh worked up to maxing out his retirement accounts each year.” Well, any journey worth taking is at least 10x harder when you’re setting out on your own, with nobody to provide feedback, guidance or a digital butt-kicking. That’s where my amazing community of personal finance friends on Twitter comes in!

The ability to converse, share, and learn from one another has been jet fuel for my progress to FI. Admittedly, I am on Twitter way too much, but when your friends are all there hanging out together, you want to join in the fun. I’ve read about friends blasting through their student loan and consumer debts, hitting net worth milestones, and retiring early. I get so much joy hearing others accomplish their goals, and it fuels me to buckle down and hit some of my own goals.

That’s not to say I don’t still have a lot of frivolous spending in my non-existent budget (I use the Anti-Budget, which I heard about from blogger/podcaster Paula Pant at AffordAnything). But when I saw the savings that other people had made with cutting their spending, I tried a few of those tricks for myself. I used the Trim app, which Tori Dunlap recommends. I cut cable out of my expenses, another popular move in the personal finance and debt payoff communities. I switched my cell service provider, leaving Verizon that I’d been with since the early 1990s and going with GoogleFi, thanks to a writeup and #promocode that Gwen from FieryMillennials wrote about.

Penny from ShePicksUpPennies helped me make the mental shift that mortgage debt is still debt, and there’s no such thing as good debt. While I may not be attacking it as vigorously as Penny and her husband are attacking their mortgage, I have started allocating “extra” money that shows up in my life, like a birthday check from grandma or a reimbursement check from work, towards the principal on my mortgage. It’s not a lot, but every dollar today saves me in interest going forward, and I’ll have that sucker paid off sooner than the 30 years I am scheduled to take to pay it off.

And how could I forget travel hacking? That has been by-far the largest tweak I have made to my personal finances, aside from maxing out my retirement accounts each year. Brad from ChooseFI had a couple of earlier sites, including RichmondSavers and TravelMiles101 that launched me down the road of travel hacking. While I wasn’t in a position to be taking any time off to travel, I was stockpiling points and miles towards future travel, which I have really been taking advantage of for the year and a half. Many of those trips are outlined here. But it wasn’t just Brad talking about travel hacking. “J” from MillennialBoss, Justin from Saving-Sherpa, Luxe from TheLuxeStrategist, and many others showed me what is possible in the travel hacking game. I’ve just been using my accumulated miles and points for simple domestic trips, some to visit my home state of Indiana, and others to take in the beauty that can be found in the Lower 48. Once I get more vacation time saved up, I will remedy this shortcoming in my travel log.

But it isn’t just tips and tricks, these are true friendships. People who encourage you in your personal and professional life. People who cheer your baby’s first steps. People who support your entrepreneurial endeavors, and share their experience with similar steps they’ve made. And for these reasons, I’ve been dedicated the past 9 months to making these internet friends into In Real Life (IRL) friends, as often as I can!

Speaking of entrepreneurial endeavors, I was honored to be able to provide a scholarship to Dumpster Doggy (Amanda Holden)’s Invested Development course. The response to Amanda’s call for scholarship applications was so great that 6 other benefactors stepped up to provide scholarships for deserving young women. But we also read the applications and saw that several of the women needed a little bit more coaching at the beginner levels of personal finance, before taking a course like Amanda’s investing 101 course. So I offered to pay for 4 of these ladies to have 1-on-1 coaching with Tori Dunlap from HerFirst100k. I felt like I am beyond the level of personal finance/investing knowledge that my friends are providing, but I still wanted to help them get their businesses off the ground. These scholarships will also help other people with their financial journeys and my friends are far more qualified and capable to help them than I will ever be! As my friend Revanche put it, sometimes you just have to put the right resources in the right person’s hands at the right time.

I was also fortunate enough to provide a scholarship to the first Elevate Influencer conference, put on by Sandy Smith. This is the first conference for financial influencers of color, and I’m happy to know that positive financial messages will be provided to many thousands of people because of my tiny monetary donation to Sandy’s efforts.

Making friends outside of Twitter

As I mentioned, I’ve been involved in personal finance conversations on Twitter since at least 2014. I watched with dismay as so many of my friends got together in San Diego in 2016 for FinCon, and then again in 2017 in Dallas with even more of my internet friends hanging out together! I swore that if there was any way I could swing it, I would attend my first FinCon in 2018, and then they announced that it was in Orlando, a mere 3 hour drive from where I live. This was something I couldn’t pass up!

And then I changed jobs not quite 5 months before FinCon and I was terrified that I wouldn’t be able to take the time off, or even convince my new boss that this was a worthwhile event for me to attend, since I’m not related to financial media in any way in my day job. Fortunately, we are awarded 3 “professional/training” days per fiscal year, so even though I was only there for 4.5 months of my first Fiscal Year, I was still able to take all 3 training days off to attend a financial media conference a.k.a. party with hundreds of my friends from the internet!

FinCon in 2018 was held at the Rosen Shingle Creek resort, which is not affiliated with any of the big name hotel chains that I had accumulated points. For this reason, I had to pay the cash rate for the 5 nights at the Rosen, which topped out at nearly $1,000 including taxes, fees, and parking. Thankfully Stephonee at PoorerThanYou gave me a parking pass that covered 2 nights out of the 5 my car was parked, or I’d have been over the $1,000 mark.

As I wrote about in my FinCon recap post, I was amazed that people at the conference actually “knew me” and were excited to meet me. This little blog you are reading had only about 15 posts at the time, fewer than 1,000 all-time page views, and it wasn’t something I was seriously pursuing (still isn’t to this day). But because I was so supportive, constantly reading and sharing other bloggers posts, I was like a mascot for the personal finance Twitter community, which is truly an accurate description of me, if I’m being honest.

I got to meet people I’d interacted with for years, like J-Money, Tanja Hester, Gwen, Brad Barrett and Jonathan Mendonsa, Big ERN from EarlyRetirementNow, J.D. Roth, Carl and Mindy from 1500days, Felicity, and Jillian Johnsrud from MontanaMoneyAdventures, and all of these were before the conference even started on Wednesday afternoon! I met so many of my favorites from Twitter, including Penny, MilitaryDollar, Erin from ReachingForFI, Piggy and Kitty from BitchesGetRiches, Tori from HerFirst100k, Annie from ChampagneAndCapitalGains, Allea from Duett, Liz from Chief Mom Officer, Stefanie O’Connell, Deanna from MsFiology, Krystel from AllSheSaves, Kevin the FinancialPanther, Mr AE from ApathyEnds, and many many more. A more comprehensive list is in the FinCon recap post, but I wanted to show here that I was able to get acquainted with so many more, in real life with just one trip!


Of course, a few days together at a conference is great, but there were 2,000 people in attendance. Even the people I spent the most time with, maybe got an hour or two of hangout time, and even that was often in spurts, or while I was Ubermyer-ing them to their Airbnb.

That’s where the next gathering came to mind. Stephen Baughier has put together CampFI retreats at 6-7 locations around the country, and it just happens that the first 2 of each year are located outside of Gainesville, FL about 4 hours away from me. Right after FinCon, while I was still riding the high of hanging out with so many of my favorite people on the internet, I booked a ticket for CampFI SE Week 2. This week showcased presentations by Joel from Fi180, Noah and Becky from MoneyMetaGame, Coach Chad Carson, Michael from UncommonDream, the aforementioned Jillian, and the YNAB master himself, Nick True. In attendance were other friends such as Brad, Seonwoo was my roommate, Deanna was there too. Bianca from Miss Mazuma welcomed me to camp, and Lisa Duke had so much fun at Week 1 that she came back for Week 2 😊


CampFI is a Friday-Monday event, with all of the scheduled action really happening on Saturday and Sunday, but there’s a lot of camaraderie and sharing your individual FI stories throughout the 4 days/3 nights, plus fun activities like a ropes course, archery, and pickup basketball. Bianca is also the organizer of my #70kchallenge, where a group of people are being each others’ accountabilibuddies in hitting an average of 10k steps every day, with a $5 penalty for coming up short during a weekly check-in. So she and I arranged a morning hike on the campus’ trails, and we had a group ranging from 25 down to 4 by the end of the weekend.

Travel hacking meetups

These organized meetups are great, but they cost actual money. As I mentioned before, I have accumulated a stash of points and miles that I want to use for traveling. But just because I’m traveling somewhere, doesn’t mean I can’t put out the word on Twitter and see if any of my personal finance friends in the area are down to meet up!

The first such occasion came in November, when I traveled to New York City for a quick Veteran’s Day weekend trip. ZeroToFire and Felicity were hanging out in Midtown, and messaged me when I touched down at LaGuardia. Luxe had made reservations for us to meet up and have dinner together at a cool taco shop near the Flatiron Building. I was able to spend most of the afternoon and evening with my personal finance friends, even on the travel-shortened day of my arrival in NYC!

Up next was my roadtrip around the Southeast for President’s Day Weekend. This was such a hastily-planned trip that I wasn’t even sure I was going to make the trip until I clocked out at work at 4pm and hit the road heading North. If I had done a better job with my plans, I would have messaged my Atlanta-area friends Lisa Duke and Seonwoo sooner. But I wasn’t really visiting Atlanta, just passing through on my way to Helen, Georgia up in the mountains. After checking out the tourist trap in Helen, I crossed over into South Carolina and visited Coach Carson’s stomping grounds, but again, I wasn’t good about making my travel plans known, and I didn’t get to see him there, either. But the 2nd full day of my trip took me to Charleston, SC, where the blogger ‘SC’ from MissfunctionalMoney hails from. We hadn’t interacted a whole lot online prior to meeting, but we share close online friend Champagne & Capital Gains, so that was good enough for both of us! ‘SC’ was a wonderful tour guide and reminded me a lot of both ‘Champ’ and Luxe, and I can’t wait to see her again at FinCon coming up in DC in 2019!

Once in February and again in March, I was able to meet up locally with Vicki from WomenWhoMoney and her husband Jeff. They’re now snowbirds, spending several months per year in Sarasota, FL, just over an hour up the road from me.

In early April, Brad and his family were on vacation in my area of Southwest Florida, so I reached out to him to see if he wanted to meet up. Brad came back and said let’s set this up as an event for the ChooseFI Fort Myers local group, so I set out to arrange the event for anyone in the community to come out and hang with Brad and fam. We only ended up having myself and 4 others show up to meet the Barrett family, but it was still an awesome time hanging out in a covered patio and chatting with new people for a few hours on a Thursday evening. A few weeks later, I was upgraded to an Admin of the local group, so hopefully I’ll be able to spread the message to a wider audience for any future events in the area.

Also in April, a conversation on Twitter led me to help organize a meetup of Florida FI bloggers in the Tampa area for Cinco de Mayo. Liz from RoseColoredWater was on break between her 2nd and 3rd semesters of Nursing school, MK Williams and her husband Jason would be traveling the rest of the month, FromOneGeektoAnother had to work that day but could stop by after clocking out, and Kristine from FrugallyReckless and her husband Michael were able to come too. I drove up 2+ hours and Seonwoo flew down from Atlanta. It was an awesome afternoon, meeting 6 new-to-me friends and being the first FI friend that Liz and FOGA had met in person!

Only 5 days later, I had one of my most unique “meetups” to date. I saw that BudgetEpicurean has a habit of calling people on her way home from work and thought it was a fun idea to help pass the time during a commute. I messaged her that it sounded like something I’d be willing to try, since I have almost an hour-long evening drive home. She agreed and called me that afternoon! We had a fun 40-minute conversation about all sorts of topics, including our shared friends and love of this community, our birthdays being super close together, and I had done work in her hometown when I was in college!

Cleveland meetups

Continuing the theme of meetups in May, I reached out to Deanna when I had a work trip taking me to Cleveland, Ohio. Deanna was gracious enough to not only set up a meetup for when I was in town, but she also came to my hotel and picked me up, then drove me back to the hotel at the end of the meetup! She’s a saint, y’all. Deanna was the only existing friend I saw at the ChooseFI local meetup, but I made a few new friends on Facebook from that event.

My conference was over on Thursday evening, but my flight back to Florida wasn’t until Saturday afternoon, so I had all of Friday free. Amanda Page lives in Central Ohio, but made the drive up to NE Ohio to spend the afternoon with me! We’ve been friends online for at least 4 years, back when I followed her DreamsBeyondDebt blog and her amazing debt payoff story. We wandered all around downtown, taking in the sights. I knew of her love of historic buildings, so I made sure to work in the Arcade into our walking path, which almost feels like you’re walking into a European streetscape when you walk through the doors. It was so incredibly generous of Mandy to make that drive (around 2 hours, each way) just to meet me and hang out for a few hours. Visits like that prove to me that these online friendships are often the real deal, even if we’ve never met in person!


San Diego – Playing with FIRE premiere

Rounding out my recent trips, I flew out to San Diego to catch the Playing with FIRE premiere at the San Diego Repertory Theatre. Jonathan posted that there were still about a dozen tickets available for purchase a mere 12 days before the showing, and I jumped at the opportunity to watch the film with the FI community where Scott and Taylor’s story in the film began. I shared on Twitter that I was going to attend, and my friend Military Dollar decided she could make a trip of it too, even buying the ticket next to me in the theatre! Military Dollar has even more connections than me, and she arranged with Jennifer Mah from the ChooseFI San Diego group to meet up earlier in the day on Saturday for brunch. Doug Nordman (Nords from The-Military-Guide) and his wife Marge were also in town, on their way back home to Hawaii, and they joined us for a 3-hour brunch at the amazing Great Maple.


After leaving brunch, Military Dollar and I met up with FrugalToFI at the USS Midway and we took a tour. Military Dollar is a huge military history buff, so it was a terrific experience to have her show us around. But I’m 6’5” and these ships were not made for tall guys, haha. I only hit my head 4 times, and I was being careful!

We left the Midway and we all headed back to our respective hotels to get ready for the showing. I arrived early to try and meet as many people as possible before the film began. I was able to meet Wendy and Curtis from HouseofFI podcast, Andi and Big Al from Your Money, Your Wealth podcast, and a whole bunch of the San Diego local ChooseFI group who were volunteering with the event. After the film, some of the cast and crew stayed for a question and answer period, and then we had an after-party at a local bar. It was great to finally meet Scott and Taylor, whose journey I had followed for over 2 years, and who I’d interacted with quite a few times on Twitter in support of the film.


Making true friendships

I don’t know what I ever did to deserve such incredible online (and IRL) pals, but you won’t find a better group than I’ve cultivated on Twitter. Penny, Mil-Dollar, Gwen, Angela, Tanja, Jillian, Champ, Stephonee, Erin, Simplistic Steph, Emilie, Chief Mom Officer Liz, Amanda Page, StephTheBlogger, Dillon, 76k, FiMechanic, Fioneers, Luxe, FOGA, Rosie/Liz, Stefanie, Matt Lane, Bridget, Des, Alyssa, Piggy, Kitty, Doggy, Tori, Revanche, Jax, TenaciousJ, Pete, Zero, Moriah, Seonwoo, Deanna, Sylvia, FrugalPharm and so many more!

Not only do we frequently have back-and-forth on Twitter, but I have daily conversations with several of them. Sometimes it’s texting, and other times it’s Direct Messages (DMs) on Twitter. Sometimes I provide notes when I find misspellings in new posts that I read. I’ve answered questions on getting started in travel hacking or maximizing the existing cards they already have in their wallet. Sometimes we just laugh and have fun conversations. Sometimes we have very serious conversations involving sickness of our dear loved ones and we provide sympathy and support. And sometimes we stick up for each other when malicious internet trolls are attacking for no reason other than to be harmful pieces of shit.

Kristi Tanner Smith

Kristi Tanner Smith is one of my newest friends in the FI community. She’s a Moderator in the ChooseFI group and also lives here in Florida, albeit some 5 hours away from me in NE Florida. I look forward to meeting her someday at a CampFI event, especially since the CampFI SE campus is slightly over an hour away from where she and her husband live.

I have yet to meet Kristi Tanner Smith, but I already know she’s a kindred spirit. Besides being a proponent of the FI lifestyle, she’s an active participant and was recently featured on an Audience Takeover episode of the What’s Up Next podcast.

Another main reason I know we’d get along quite well is because she refuses to allow big-name bloggers to use their platforms to lie to their readers and will call them out on their lies. When I first wrote this paragraph, I was going to be super harsh on Financial Samurai for his fabrications about me and my friends, but now I just feel pity for him.

He’s successful by any measure: early retired, married and has a young son, net worth over $10 million, a blog with millions of page views. And yet, he still goes after relative nobodies. Kristi isn’t a blogger, and I’m not much of one. I don’t think I’ll ever understand why he feels threatened by people who are just telling him to stop lying to his readers. I guess he doesn’t have the benefit of such a positive, supportive community like I enjoy. And so I feel sorry for him, not anger towards him.

Online community

And so it is. We take the good with the bad, and there is FAR MORE GOOD in this community than the few bad apples. I will continue to travel and visit with my online friends as often as I can manage, because they remind me why I am on this path to begin with – to spend time with people I care about. Certainly, I could reach my FI date sooner if I skipped some conferences, camps and trips, but the events I described above have been the absolute highlights of my life in the past 9 months. The scholarships I paid for helped support my friends in their entrepreneurial endeavors and helped in the education of 6 other people I may never interact with.

Even with the thousands of dollars I have spent on travel, conferences, blogging, podcast microphone, etc., I am still tens of thousands of dollars ahead of where I would otherwise be without this financial information on the internet and accountabilibuddies that help me along the way. There’s no “perfect” way to manage your finances, but we can continually learn from one another about different ways that have worked for us. We can help others avoid some of the financial pitfalls that we’ve found for ourselves. That’s the whole point of my blog, to share some of the stories that I have gone through on my journey from -$150,000 in 2010 to a future life of Financial Independence. And I wouldn’t want to be on this ride without my FI community online.

  1. We simply don’t deserve you, Josh. I am so glad that you started blogging, and I’m even more thankful that I get to count you as a friend. All of our convos mean so much to me, but I will honestly never forget you taking the time to find us so early in the AM at the last FinCon to say goodbye. You are just the best <3

    1. I didn’t have a chance to see you on the Saturday night, since the crew I was hanging out with was poolside from 7pm-3am, so my last chance to say goodbye was bright & early! But I was a sobbing mess all morning, saying goodbye to everyone. You all mean so much to me!

  2. Wow, loved reading this Josh. You really are a community connector. I hope to be fortunate enough to meet you in person someday!

  3. This is so wonderful! Your passion for developing strong relationships while optimizing your financial growth is fantastic. I think it’s so refreshing when people prioritize connections with others 🙂

    I’m bummed I couldn’t make it to the Cleveland meetup, but like PFI I hope we’ll meet sometime too.

    1. Yep, I definitely want to meet you too! Love my Midwest folks (I grew up in Indiana but moved to FL and right out of college)

    1. Definitely a little too soon, but I appreciated that you gave me a couple suggestions on things to do/see in the area. And yes, way too short of notice. If you recall, I booked the whole trip 5 days before it started, and I didn’t reach out to you until I was already on the train up from LA. For a person with a degree in PLANNING, I sure don’t plan ahead very well! 😂

    1. Well not right now 😂 but yep, I’m in the Fort Myers area and work in Port Charlotte! Not too terribly far away from the Tampa Bay area

  4. Josh you are the king of community in FIRE. I nominate you for the official FIRE mascot. Looking forward to seeing you again this weekend. BTW there are lot of good looking people in that CampFI photo.

    1. Thank you, Sir! I’m looking forward to a great event tomorrow evening, catching up with my FIRE friends and making new ones!

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