FinCon 2019 Recap

My trip to FinCon in Washington D.C. was sponsored by Upstart. All opinions are my own.

So if you’ve been following along, you know I was just at FinCon in Washington D.C.! Let me tell you, I still haven’t fully recovered from this trip because #old. FinCon was a whirlwind and such a blast! I learned so much from this trip. 

FinCon is a conference for people in finance media, including bloggers, YouTubers, podcasters, and brands. In case you are confused why in the world I was there, I attended with Upstart, an online lending platform that knows you are more than your credit score. Upstart’s underwriting is powered by a machine learning model that uses over 1000 different attributes including education and work experience  to more accurately determine your risk as a borrower.


Upstart was founded by ex-Googlers and their mission is to enable effortless and affordable credit based on true risk. Upstart partners with banks to provide unsecured personal loans from $1,000-$50,000.* A personal loan from Upstart could help with anything from credit card debt consolidation, moving expenses, wedding deposits, or medical bills. 

I’m actually a borrower with Upstart. A few years ago, I applied for a personal loan to help consolidate my credit card debt. The application process was incredibly easy and I had the money in my account the next day. Check out my first FinCon post to learn more about my history and experience with Upstart. 

Upstart was a fabulous sponsor for this event. Keep reading to check out all the cool things they did at FinCon. 


FinCon was nothing like the other blog conferences I have attended.  For starters, there were male attendees. I had never met a male blogger until this conference since I live in the lifestyle blogosphere. It’s so interesting to see how men and women tackle social media and blogging differently. Some of my favorite moments from FinCon came from talking strategies and tactics with other bloggers. Everyone was SO friendly at this conference and so willing to share their secrets to success.

Another major difference, obviously, was the content! I was a bit like a fish out of water when it came to the finance sessions. I stuck to the blogging and business sessions since these were full of fresh perspectives outside my niche. 

I am so happy I went and LOVE the finance blogging community. I’m so thankful for the connections I made and the opportunity to partner with Upstart. 

Buckle in folks, this is a long post. Let’s recap!

DAY 1:


I flew in to Washington D.C. on Tuesday morning. The conference didn’t start until Wednesday so everyone was still preparing and getting ready for kick-off. I briefly caught up with the Upstart team to say hello, then explored the area around my hotel a bit, ate lunch, and took a nap lol. Traveling makes me super sleepy and I was recovering from a cold, so that nap was essential. Also, is there anything better than zonking out in a hotel bed by yourself? Answer: absolutely not. It’s the best.

That night, a lot of FinCon attendees went to the Nationals baseball game! I didn’t know a SOUL going into this and I’m an introvert so I had to man-up a little for the first event. Like I said, everyone was SO nice so I worked myself up for no reason. It was really fun and really interesting to explore another stadium other than Suntrust Park. I met some great bloggers and really started to get excited for the conference to officially begin.

DAY 2:

Wednesday was the first official day of the conference. We kicked off the day with a little meeting with Upstart. I was so grateful to be an Upstart Premier Partner for this conference along with my new friend Brian from Debt Discipline. Upstart was a sponsor of FinCon 2019! They really sparkled at this conference, but more on that in a few.

After our meeting, Upstart hosted a brunch for some of the bloggers attending the event at Ted’s Bulletin. The bloggers in attendance were: The Finance Twins, The Money Mix, Arrest Your Debt, Money With a Purpose,and Ms. Fiology. This brunch was one of the highlights of the conference for me. It was fascinating to listen to everyone’s story of how they got into blogging, why they are passionate about their topics, and their different strategies for success. 

Following the brunch, we headed to check in to FinCon! The very first thing I did was head to the first-timers orientation. Your girl was a little deer in the headlights, so this was necessary. I clearly was not the only one feeling a little lost because this session was jam-packed. The speaker gave great tips for coming into FinCon with a plan and a strategy for what you wanted to achieve while you were there. 

After the orientation I went to explore FinCon Central, the expo part of the conference. Now this was the coolest part of FinCon! All of the sponsors were in one giant hall and displayed their brands in creative booths with some awesome swag. I got my face printed on a macaroon, played lots of games, and got to do a lot of networking. 

Now remember when I said Upstart really sparkled at this conference? They EXCELLED in the expo. They had an artist drawing digital caricatures like the one I posted before the conference. Upstart also did a giveaway of a North Face vest every day of the conference. Finally, they had a truck driving around Dupont Circle with a digital billboard on the back. Every day, they hosted a social media contest to give FinCon attendees the chance to have their caricature featured on the truck. The first day, Brian and I had our caricatures featured! I never saw the truck, but Brian got a glimpse. Here is his photo. All credit to Brian at Dept Discipline!


The first day of FinCon ended with a kick-off party at The Smithsonian’s National Museum of the American Indian. This was an amazing party complete with DJ, rooftop hangs, and a donut wall. Plus the museum exhibits were open so we got to do a little exploring.

While I was at the party, Hubbs made it to Washington! We went for a late night burger to catch up on the past two days.

DAY 3:

Despite my late night hangs, I was up bright and early for the keynote speaker. This year’s speaker was Ramit Sethi. Again, in case today is your first day here, I’m not a finance blogger but I did get a lot out of this talk! Ramit gave great advice to think about what you like to spend money on and then imagine what that would be like if you had 4x the money to spend on it. The talk encouraged the audience not to think linearly. I came out pretty inspired and challenged to get my finances in tip-top shape! 

On day 3, I attended two sessions for a special project I’m working on and I don’t want to spoil the surprise until everything is finalized. So for now, I’m just going to say I attended some awesome sessions on blogging and growing your brand. Stay tuned. Wink wink.

After I had wrapped with FinCon for the day, Stephen and I packed in an afternoon of sight-seeing.  By packed in, I mean we did the speedy version so we could see as much as we could. I hadn’t been to D.C. since high school, so I really wanted to sneak in some time for monuments and museums.

DAY 4:

I found one of two other non-finance bloggers at the conference! I met Valerie from Wellness & Wanderlust! We went to breakfast and then went back through the FinCon Central expo hall. Yes, it did take me three days to get through FinCon Central. It was that big. 


It was the last day of the expo so I really tackled it head-on this time. Before I had just been wandering around aimlessly, but this time I was motivated to get through it all so I spent a few hours visiting the booths.

One of my favorite events, The Plutus Awards, capped off Day 4. This event celebrated the bloggers, podcasters, and YouTubers who excelled this year. Several of the bloggers I met at the Upstart brunch were nominated so I definitely wanted to attend! 

The Plutus Awards were so much fun. This event gave me the opportunity to discover new blogs to check out in the finance space and helped put a face to the name of some I already followed. It was just a touching and hilarious night, and I really really enjoyed getting to experience this event.

Final Day:

The final day was a day to network, sightsee, and tie up any loose ends before we all headed home on Sunday. Stephen and I did another jam-packed afternoon of sight-seeing before the closing party that night. 

The closing party was red, white and blue themed and it was a great opportunity to say goodbye to all the new connections I made during the week. 

I’m so grateful for the opportunity Upstart gave me to attend FinCon. I loved getting to expand my network and meet so many cool and unique bloggers. I came back with a whole list of things I want to do and am really inspired right now for my both my blog and my business.

What’s the best conference you’ve ever attended?

**“The full range of available rates varies by state. The average 3-year loan offered across all lenders using the Upstart Platform will have an APR of 20% and 36 monthly payments of $35 per $1,000 borrowed. There is no down payment and no prepayment penalty. Average APR is calculated based on 3-year rates offered in the last 1 month. Your APR will be determined based on your credit, income, and certain other information provided in your loan application. Not all applicants will be approved.”


Hel On Heels is an Atlanta-based life and style blog by Helen Gaillet Bailey. Hel On Heels is intended to be a digital magazine written by your best friend.

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