Resurfacing From Radio Silence: An Update on the Past Two Years of My Life

I’d like to start by saying that I’ve missed you guys! The last two years have been a whirlwind from the growth and expansion of my consulting company (and turning it into a nonprofit), founding an EdTech company, making the Forbes 30 Under 30 list, and of course, moving to Princeton and starting seminary. There’s been so much to thank God for and I’m excited to share some of the highlights with you all.

The Expansion and Transformation of S. Montgomery Admissions Consulting

Even though I started working with students during college and throughout law school, I didn’t officially launch “S. Montgomery Admissions Consulting” until I graduated from law school in 2018. For four years, I grew the work that we did with first-generation, minority, and immigrant college and law school students under that brand. However, in 2022, I embarked on a project to increase access to more students by building an edtech software platform. Outline It was born halfway through 2022 as an interactive writing platform helping students draft better outlines and essays. We moved the consulting and the entire company into the Outline It, Inc. C-Corproation as we began our journey of getting investors and becoming a true venture-backed early-stage startup. We also started year one of a two-year pilot collaboration with the Law School Admission Council where we served 2,800 students with law school admission advising and gave them access to the Outline It writing software. 

We were so blessed to gain acceptance to several accelerator programs (Halcyon, Expert Dojo, Visible Hands, New Schools) and also get backed by generous and supportive friends and family and angel investors. Because of our success, we were named at the end of 2022 as one of the best 200 pre-series A edtech startups in the world (Elite 200) by the GSV Cup. We traveled to the ASU + GSV conference in April 2023 to represent Outline It at a conference of more than 7,000 entrepreneurs, investors, and educators. To date, Outline It has served over 5000 students, by helping them reduce writer's block and streamline their thoughts, all while giving educators more insight into their students’ pre-drafting process.

Toward the end of 2022, however, I started hearing from God that He wanted me to move the consulting and advising work I was doing with students into a faith-based nonprofit. This rebrand better reflects our commitment to breaking down barriers and creating opportunities for all students and represents our goal of making education accessible and achievable. As a result, when 2023 started, I was the Founder & Executive Director of the Barrier Breakers nonprofit and the CEO & Founder of Outline It, juggling both companies as they were growing in different directions. 

Despite my best efforts, however, God ultimately let me know that Barrier Breakers was where He wanted me to focus. We were able to get more investment into Outline, and in total, we raised over $1M in dilutive and non-dilutive funds toward the venture. However, the rise of ChatGPT and Open AI coupled with our inability to successfully sell into schools and school districts led to us running out of runway over the summer of 2023. While I am still hopeful for a soft landing and exit for Outline so that the software can continue to be useful for students, I know that it is fully in God’s hands. 

Personal Life

None of these changes would have happened if I hadn’t been listening and attuned to God’s hand directing my decisions. Many of those decisions, I attribute to surrounding myself in a faith-community that continues to push me, challenge me, love me, and support me. Moving to Princeton, NJ in 2022 and starting at Princeton Theological Seminary was a huge change in my life but one that is faithful to what God called me to do. And who am I to say no to God?! I started enrolled in the Master of Divinity and Master of Arts in Christian Education Formation dual program and its  been wonderful getting to grow in both head and heart knowledge through the wisdom of the staff and students at the seminary and of course the help of The Holy Spirit! And while I did decide to take a leave of absence from seminary after this semester to focus on Barrier Breakers, I am excited to see how God will use my training here for His glory.
I’ve also been enjoying building a life with my partner Richard and taking up a new hobby of indoor gardening (you can check out my Instagram reels for evidence of this obsession!)

I also started a new podcast - Serenity For Success, which is a podcast for ambitious women seeking a deeper connection to faith and purpose. It includes short meditations helping women ground themselves in truths from God’s word and interviews with other successful Christian women. You can check out the podcast on Spotify and Apple Podcasts!

Oh, and I turned 30 back in February! There’s always a sense of gratitude and nostalgia looking behind and excitement looking forward when entering a new decade. A mixture of ‘wow, I can’t believe God did that’ and ‘I wonder what He’ll surprise me with in the next 10 years.’ I enjoyed multiple celebrations with my friends and family who made me feel loved throughout! 

Forbes

Of course, one of the most exciting things that’s happened in the past 2 years is making the Forbes 30 Under 30 Social Impact list for my work with Barrier Breakers! Finding out I had been nominated was such a surreal feeling. I have always been so inspired by those who have made the list in previous years, so it is such an honor to have been named on the list myself, especially as typically there are more for-profit founders who make the list. I also was accepted in the Forbes Nonprofit Council, which has  provided me with exciting opportunities such as writing articles every 6-8 weeks and getting to learn and network with CEOs of major nonprofits such as Goodwill, Habitat for Humanity, and others. The Forbes community has given me opportunities to attend amazing events such as the Forbes 30/50 Summit (which you can read more about here.)

I am looking forward to giving you all a more regular insight into my life and how God is moving and opening doors for me (such as my upcoming Tedx talk!). My hope is that this blog will inspire you and encourage you to continue to follow God’s path and direction for your life and trust the process!