E115_Lindsey_Simmons_Transcript
Guest: Lindsey Simmons, Founder, LindaInHR
Host: AJ Riedel
Episode: 115 | Air Date: June 16, 2025
From Layoff to Launch: The Decision to Go Independent
AJ: Take me back to the end of 2024. You've just been laid off, you've spent 6 weeks hunting with your dog, sitting with yourself for the first time without something next lined up. Walk me through what that actually felt like.
Lindsey: It was... I was at a point in my life where I was ready for uncertainty. Where at earlier points in my career it may have given me a lot of anxiety, and I might have been thinking, what do I do — this was more excited to reflect, and excited for time to really think and make more clear decisions around how I wanted to move forward.
Being able to really take not only this initial 6 weeks of wrapping my head around "alright, what's the plan, what am I gonna do," but really ultimately taking about 6 months to be outside, hike, think about what I'm looking to do, what have I done, what did I like, what did I not like, what do I want to bring forward, what do I want to leave behind. So it was really just a big time of self-reflection and introspection.
I think it was further enabled by the time I was able to be outside and hike with my dog, to go hunting, to just be in nature, and away from the screens that I've spent most of my career on. And it let me understand I enjoy the work that I do. I just want to do it differently.
I had a lot of conversations with mentors and people I really admired and had partnered with over my career. And I had actually bought the web domain for LindaInHR in 2020. I just knew at some point I wanted to do some sort of consulting — I didn't know what that really looked like.
My first consulting client — I was actually speaking with her because she's also become one of my closest and dearest friends. And she said, "You've been talking about this since we met. This is your time. What are you doing?" I was like, yeah, actually, thanks for helping me connect those dots. It's just so funny — the things you can connect yourself, and then what you need others to help you see.
So I started to build my first version of the LindaInHR website — bless its heart. And then realized paying designers is definitely worth every penny. And I got connected with another fractional group, Three Hive Strategy, and was freelancing with some of their clients, and then started to get some of my own clients referred. It's just kind of been a real evolution.
The Uncertainty of Starting: Process, Niche, and Building the Plane While Flying
AJ: During that whole evolution time, what was the one thing you were most unsure about?
Lindsey: How I was doing what I was doing. It really was — this phrase is so overused but it really was — building the plane as I was flying it. I'd obviously been in-house and had consulted a little bit, but just figuring out: what is my process? Who are the people I want to work with? Are there areas I want to focus in?
I was definitely afraid of niching down and having that be a limiting factor. But when you zoom out, it's like — I'm one person, so guess what, this is going to be relatively finite. So that's actually a good thing, not a bad thing. But you also kind of learn as you go. You say yes to things that are totally new. I said yes to working with a particular industry I had no experience with — but turns out, as a recruiter, you can adapt. I can learn what I need in almost any industry and find really excellent people within it.
So it was both a lot of navigating uncertainty, but also telling myself: how many years have you done this? You have the experience to do this. Just show up and do what you know how to do. While there was uncertainty, it was also navigating and managing the self-talk — because I think that's really what trips people up the most.
AJ: It sounds like you recognized a resistance to niching down — seeing all the advice that says you've got to niche, niche, niche. And you resisted that, and you also took some clients that were outside of your industry. How did you ultimately land on your niche? Who is your ideal client?
Lindsey: I think it really goes back to where the bulk of my experience has been, which is B2B SaaS companies — now also working with more PLG and AI startups — and really focusing on building hiring processes, with a focus on technical, product, design, and engineering hiring. Still being able to tap into G&A and go-to-market when needed. Doing what I've done and knowing what I know, I feel most comfortable and competent in the B2B SaaS and more AI-forward space.
But I've also enjoyed working with clients in CPG, mechanical engineering, structural engineering, and renewable energy. I'd say my bread and butter focus is really B2B SaaS. I can hire anybody within those companies.
AJ: SaaS is Software as a Service. What is PLG?
Lindsey: Product-led growth companies. It's more of a long tail — you've got a lot more individual user customers, and can also scale up to the enterprise level, but just a much broader customer base that is less sales-focused.
AJ: You've worked with other kinds of clients and taken jobs in other areas. I know from my own experience, I strayed outside my very narrow niche once into a very different industry, and it did not go well. It sounds like you haven't had that same experience.
Lindsey: I think when it comes to hiring, it's a lot about process — understanding what you need in a role, and being able to help leaders get really clear on the experience profile they're targeting. Then what that process looks like, who they want in the interview conversations, and what they're evaluating. Through those conversations, you can really understand a company, an industry, a team, and what that specific type of role needs.
If I maybe strayed into academia — my mother worked at a university for her whole career, and just hearing their hiring processes was very out of my depth. I think if there was something I absolutely didn't understand, I would have flagged it and said, "I don't think I'm your girl, but I can certainly help you find someone who's going to be a real value add here." Ultimately it's just focusing on the overall process, walking through those steps, and having those conversations — that's what allowed me to really learn, understand, and get up to speed pretty quickly.
AJ: It sounds like your process is what enables you to do that.
Lindsey: Exactly.
The Referral-Only Pipeline: How It Works and Why It Doesn't Create Anxiety
AJ: When we talked earlier, you said that every single client you've landed has come through referrals. That's a real strength — but it can be both a strength and a disadvantage. What does it actually feel like to run a business where the next client is always one relationship away from showing up or not? You're dependent on referrals for getting those next clients, which builds in a certain amount of uncertainty. How does it feel?
Lindsey: It honestly feels really validating. I feel very honored that people I've worked with see me as a trusted partner — that they would refer their former clients, friends, and professional connections to work with me.
Also, because it is just me, I'm more acutely aware of how much work I can take on. I also have my own network of referral partners that I work with, so when things come in and I don't have capacity, I can hand off with confidence and know that these relationships are still intact, and people are getting the support they need.
I don't really consider it something that gives me anxiety. It's something that really helps me lean more into gratitude.
AJ: Have you ever had a month where you didn't have a referral coming in — where your pipeline was empty?
Lindsey: I honestly have not. Timing-wise it has really worked itself out. And where I've had referrals come in that I don't have capacity for, that's allowed me to hand off more strategically, which has been great.
AJ: So you've had the opposite problem — too many referrals, not enough capacity. Which is a nice place to be.
Lindsey: I don't hate it. I really am grateful for it and appreciate the confidence it represents.
The Hardest Part: Identity, Permission, and the Internal Mental Battle
AJ: You described your first year as high and low, and you used the term "building the plane as you're flying it." What was the hardest part of that — not logistically, but the actual experience of not knowing what you were doing and going forward anyway?
Lindsey: It was really a confidence issue. Knowing that I can do these things — and then also thinking: who am I to just be hanging up my own little shingle and starting my own shop? It's more of a permission structure. Who am I and what am I doing?
Whereas I'd previously tied the rest of my career and a lot of my self-worth to the company I worked for, the title I had, all the bells and whistles. Over that 6-month period of reflection, I realized those things didn't give me what I thought they did — it was more like feeding the ego. And when you don't have that, it really is: who am I as a whole person, and how does that show up professionally?
Because for my job, I'm on LinkedIn all the time. And everybody's like, "I'm so great, I'm doing this, I'm doing that." I thought: who am I to talk about me, and myself, and this little HR recruiting consulting practice I want to stand up? So it was more that internal mental battle. Just having to redirect the internal monologue: you know how to do these things, you are doing these things, so let's keep going.
AJ: I love that. You just articulated something that will resonate with listeners. Most of us when we were starting out went through that "who do I think I am" moment. All these other people on LinkedIn have years of experience and big track records, and you're just starting out. And I like that you recognized the mental work, and that you did the mental work to bat that question away. There's a part of our brain that says "who do you think you are?" — and you were able to overcome that voice by reminding yourself you've done this, you've got the expertise, you're doing it.
Lindsey: Yeah. And I will say — during that time, I was also learning a lot of new hobbies. Learning to shoot sporting clays, learning to field hunt, learning to fly fish. Those take a real sense of presence and focus. When you're learning those things, it really helps you understand how to quiet your mind and be present and get clear on what you're doing.
Being able to bring that same level of practice and focus to my work life — talking to myself: I am someone who is learning to fly fish, I've caught fish, I've shot clays, I've hunted birds, I can do all these things. I've done this work for many, many years. So it was just that convincing of: yeah, I'm capable of doing this, it's going to be fine.
Building a Second Revenue Stream: Touch Grass and the Retreat Business
AJ: So you've got the whole recruiting piece. After a couple of years, you feel like it's kind of humming along — you're getting enough clients through your referrals, that business is going pretty well. Now you're building a whole other side of your business: bringing leaders outdoors to learn fly fishing. This is a passion, and you're translating your corporate event background into something completely new. Tell me everything — who is it for, what do they walk away with?
Lindsey: I'm focused on women leaders in tech — specifically because that's who I work with. I went to my first big fly fishing trip last summer in Montana. I fished the Madison River with Real Women Fly Fishing Adventures. Their guides were incredible, and I got to fish with Lorianne Murphy and Rachel Finn, who are two absolute icons and really strong women who are some of the original leaders of the fly fishing space.
I really appreciated how they communicated. They set a really clear tone at the start of every day, grounding everything in safety. Instructions were clear, real-time, actionable feedback. Because they started every day with the safety structure — how things are gonna work in the boat — and then we built on that from there. I became a much better angler by the end of the week.
I was thinking about how if they had communicated in a different way, it could have been a really different and unpleasant experience. But it was really encouraging, really supportive. And I was thinking about how many conversations I've had over the years with leaders who are uncomfortable with feedback conversations, or who are too wrapped up in their work — and how much being on a river, out of self-service, focused on the water, overwhelmed by beautiful mountains, just being out there...
It really requires your whole focus, calms your nervous system, and puts you in a place where you genuinely feel your own smallness. When you're sitting behind your laptop doing your day-to-day, you can think the weight of the world relies on what you're doing. When you're out there, you realize it does not. Everything is going to be fine. And so it really helps with a perspective shift on how you view yourself within your own work.
So I said to Lorianne: "I think this could be a really great opportunity for a lot of women leaders I work with. I just want to get more women on the water — so why not?" And she said, "That sounds like a great idea. Let's build something." And so we're building a retreat called Touch Grass to get more women leaders out on the water and bring this patient, present practice back to their own work.
AJ: And how are you getting the word out?
Lindsey: Posting on LinkedIn, doing individual outreach, and Lorianne's fly fishing network — she's also putting it out in her newsletter. It's on my website as well.
AJ: You're launching in July. How many people do you have signed up?
Lindsey: The retreat is the last week of July. So far, we have 4 people signed up. We have 10 spots total. We're really excited for the first year of our Touch Grass adventures, and excited to continue to build out for next year too.
AJ: Does this feel different from how you built your recruiting side of the business?
Lindsey: Yes and no. I did more big corporate events and retreats when I worked in finance and was doing campus recruiting, so I'm taking that skill set and putting it into this capacity. But this is also the first time I'm doing this, so it is new and unknown, and there are a lot of variables.
I keep talking to myself and saying: you're surrounded by people who do these things, you're being guided by people who've done this, so just trust the process and know that launching anything the first time can be uncertain. Also, trusting myself to figure it out.
AJ: You said "figuring it out in real time." What does that actually mean day-to-day right now?
Lindsey: Day-to-day is tightening up the programming schedule and learning about how to get event insurance and all the other safety precautions I'll need — and just making sure I am providing a really great experience that is as safe and comfortable for everyone as possible. Constantly thinking through different details and emailing back and forth with Lorianne to gut-check myself: are we good here, do we think we need something else? It's been a real collaborative process that's been really fun.
Juggling Two Businesses and Looking Ahead
AJ: What's the biggest challenge you're navigating right now?
Lindsey: I was navigating more of a logistical issue with figuring out how to get a lot of the swag designed and delivered, but I just connected with a really amazing company that is going to do all of it for me, so that has taken a lot of stress off my plate.
AJ: Right now, the recruiting work and the search work and the retreats — I would assume the retreat is taking a lot of your time because it's coming up.
Lindsey: Yes and no. During the day I'm focused more on the recruitment consulting, and then in the evenings is when I'm doing a lot more of the Touch Grass work. Tech Week for New York City is next week, so I'll be going to some of those events — also partly because last year when I went to Tech Week events, I was talking about my hunting and fly fishing, and everyone was so excited about it. So it's like, well, maybe I'll pop back in and get the word out that I've built something.
AJ: Somewhere in this journey over the last couple of years, you realized that your true passion was being in community with women leaders outdoors. Take me back to the moment you knew that.
Lindsey: Honestly, I think it might have been the first time I went — I'm on the board of Juliana's Anglers, which is a ladies' sporting club — and the first time I met up with them was for a sporting clays lesson. I was so nervous. I didn't know anybody. It was totally new. Everyone was so welcoming and encouraging. Even after our lesson, we met up with the experienced shooters on the course, and everyone was just having so much fun. It was such a joyful, beautiful day outside.
On my drive back to the city, I was just reflecting: I hadn't experienced anything like that before, and I wanted to spend way more time and energy doing things like that with that group. The more I've done that, the more I've realized I want to just try to bring more people into this circle.
AJ: You're two and a half years in. Are you ahead of or behind where you wanted to be?
Lindsey: I would say I am ahead of, and just in a different place than I thought I would be — because the retreat stuff really just happened as an idea a year ago, and not something I'd ever really considered. As far as the consulting piece, I think I'm definitely much further ahead than where I would have been, and it feels good.
AJ: Where do you see your business — both sides of it — in the next 3 to 5 years?
Lindsey: I'm hoping to really continue to strike a balance with the recruitment consulting. I really enjoy that work, really enjoy helping leaders build thoughtful processes and hire great people. And I also want to spend more time outside. So hopefully I'm looking to really build out the Touch Grass ecosystem into a broader sporting leadership retreat experience — not only fly fishing, but an opportunity to do sporting clays, learn field hunting, learn horsemanship. Really excited to get out on the water and start with Touch Grass, and then continue to expand that as well.
AJ: What do you think the biggest challenge is you're going to face in getting where you want to go?
Lindsey: I love New York City so much, but I think it is coming time to find some bigger space outside of this city that I love. That move is probably going to be the biggest challenge, but I think I'm just going to end up going north of the city so I don't have to be too far away from it.
AJ: What about the whole business development area — building the businesses?
Lindsey: I think continuing to get the word out and build the community. I'm again learning as I go on marketing and community building, and that, I think, is going to be an interesting learning curve to walk through.
AJ: One last question. As you know, the title of this podcast is Thriving Through. Are you thriving?
Lindsey: I would say yes. Thriving through — thriving through chaos is really what it is.
AJ: And with that, thank you so much, Lindsey, for being on the show. For those of you listening or watching, Lindsey's contact information, her website, and her LinkedIn URL will be in the show notes. Lindsey, thank you for being on the show.
Lindsey: Thank you again for having me. This was so fun — I really appreciated the conversation.
AJ: I enjoyed it. And for those of you listening or watching, until next time, keep thriving through.