Alaia Williams is a business operations strategist, speaker, and community cultivator. She connects business owners with the exact resources they need to optimize their business. As the creator of the Entrepreneur Connection, a 900-member strong networking group in Los Angeles, Alaia knows first hand that when people connect in community, they learn and grow, and their business gets exactly what they need to thrive.


In This Episode

In this episode of Modern Ontrapreneur, Alaia Williams sits down with Landon Ray to discuss how she adjusted her pricing model to succeed at freelancing, why planning carefully for your entrepreneurial journey early on is important, and how email marketing should be the bare minimum system in any business.

Topic Timeline:

1:26 Don’t Quit Your Day Job

There are peaks and valleys, so be prepared during financially hard times.

3:57 Pricing vs. the Way You Charge

Changing from an hourly rate to a packaged pricing model.

5:49 Networking and Speaking

Webinars, livestreams, workshops and in-person events help bring in more leads.

6:25 Systems in Your Business

Most businesses have systems and processes in place whether they know it or not.

7:00 The Bare Bones System

If nothing else, make sure you have an email marketing system in place.

7:55 Getting Smarter With Facebook Ads

Facebook is a massive platform with loads of opportunity for entrepreneurs of any size.

8:18 Foster Connections

You aren’t alone; there are others out there who have been through the same situation and can help you.

9:11 Get Out of the Weeds

In order to grow, you’ll have to learn to delegate.


People have systems in place, whether they realize it or not. They either have the wrong systems for their business, or they’re not utilizing them fully.

– Alaia Williams

Show Transcript:

LR: Welcome to Modern Ontrapreneur, and today I have Alaia Williams, who is a business operations strategist, speaker, and community cultivator. She connects business owners with the exact resources they need to optimize their business. As the creator of the Entrepreneur Connection, a 900 member strong networking group in Los Angeles, Alaia knows first hand that when people connect in community, they learn and grow, and their business gets exactly what they need to thrive. Thank you so much for being here.

Alaia Williams: Thank you for having me. I’m excited.

Landon Ray: Yeah, so tell me, it’s cool to be a connector, but what is your actual business? Why do you earn money, or do you charge for connections?

Alaia Williams: I don’t charge for connections, but I charge for other related things. Primarily, I’m a business systems strategist, as you mentioned. So, day to day, I help get the right systems and processes in place to help them grow their businesses.

Landon Ray: Got it.

Alaia Williams: After I launched my business, it grew into other things like the Entrepreneur Connection, where my focus is connecting entrepreneurs through events. So, I don’t charge for the connections, but I charge for events.

Landon Ray: So, how long you been at it?

Alaia Williams: Ten years.

Landon Ray: Ten years. So, if you could go back to a ten years younger you and give yourself a piece of advice that would have eased the struggle, what would it be?

Alaia Williams: It would actually be, don’t quit your day job so quickly.

Landon Ray: Interesting. And why?

Alaia Williams: I think a lot of people get excited about what they’re after, and they jump, and they leap, and that’s what I did, and I think it would have been better to stay at the job I had for a little while longer, plan a little more, save a little more, because I was not prepared for the peaks and valleys of entrepreneurship. So, I think if I was, if I had more of a cushion, financially, I could have smoothed out some of those dips in the road.

Landon Ray: Yeah, it sounds like you’re not saying trauma that probably happened, like there’s some trauma there.

Alaia Williams: Yeah, yeah, you know, hindsight’s 20/20, but I definitely think planning out my business a little bit more, saving, would have been a smart move.

Landon Ray: So, would you have recommended nights and weekends-ing it, until you got real traction, or would you have just planned more and had a nest egg, and then taken a leap? Or what would have been the best strategy you think?

Alaia Williams: Nights and weekends, for sure. I would have snowballed my business more, more clients, more income. Then, maybe switch from a full time job to a part time job versus just leaving the job completely and being off on my own 100%.

Landon Ray: Interesting. We, as entrepreneurs, we do want to dive in, but also there’s something about desperation that’s not particularly attractive, and when we get ourselves into that place where we’re like, “Holy crap, this is way harder than I thought. I need this next customer,” it’s almost like a customer repellent, right?

Alaia Williams: Oh, yeah.

Landon Ray: And when you have the confidence to pick and choose a little bit more, somehow things work out better, right?

Alaia Williams: Yeah, and I think I felt like I was very successful, in the beginning, because I was constantly booked, but what I didn’t know was that I wasn’t charging enough. These are things that I didn’t think about. So, because I was charging the same rate that I was making at my day job, I felt like I was doing well, and I was wondering why I was getting so many clients, but it was because I was charging less than other people in my industry. My rates were way too low, and so people were like, “Sure.” So, I was running around town, spending gas, not tracking mileage. I really wasn’t planning, but I was excited about what I was doing, so that’s why I just jumped in. So, if I had thought about that a little bit more, thought about my pricing, there is still plenty of mistakes you can make along the way, it wouldn’t have been perfect, but I could have alleviated some headaches, for sure.

Landon Ray: Yeah, so what was the … at some point, you kind of figured that out, and probably made a … it shifted then, was it just the shift in pricing?

Alaia Williams: No, it was the way I charged sometimes versus the pricing. So, from hourly to packages and retainers, that was a big one, but also growing my network, and that’s where the connections kind of come from. I started my networking group. I spent time connecting with entrepreneurs, because before I started networking, I didn’t know entrepreneurs. My friends all went to Master’s programs or nine to five jobs. There were no entrepreneurs in my family. So, once I built a community and felt supported, and had other people referring business to me, or suggesting that I speak somewhere, or teach somewhere, that really changed. So, more business was coming in. I was making more, because I was charging differently. So, I think two of those things are probably the biggest things that helped me make that switch.

Landon Ray: What was the one thing that made you realize that you needed to make the switch?

Alaia Williams: I was burning out.

Landon Ray: How many years was that in?

Alaia Williams: Oh my gosh, probably about three years in. When I started my business, I was primarily helping people organize their homes. I wasn’t focused on the entrepreneurial side. So, faced with the recession, and people feeling like organizing my home is a luxury, why am I gonna deal with this now, I had to think. How do I push forward with my business? So, I changed my pricing, and also having so many entrepreneur connections now, I thought, maybe I should focus on helping entrepreneurs and teach them some of the things I’ve learned while growing my business. So, I made that switch, changed the pricing. But yeah, it was the recession, and being burned out, and driving all over LA in crazy traffic. From clients all over town, and still feeling like I’m working 50-60 hours a week, and not making enough money. This just isn’t working. Do I make a change, or do I just go back to whatever I was doing before, sitting in an office? And that was a big motivator for me.

Landon Ray: Yeah. So, now it’s working, and what is it … obviously, the networking is one piece of it. Does 100% of your business come through this networking thing or do you have other things that’s working to drive customers for you?

Alaia Williams: It’s … a lot of the business systems stuff, speaking, training. I love to teach, so I produce events. I speak at other events, so people get exposed to me that way. I love to teach classes, so I do a lot of that through the Entrepreneur Connection, but I’ll do workshops, webinars, live streams through my own consulting practice. So, it’s great, because I get to do a lot of things that I love, and income comes from a lot of different places.

Landon Ray: And when you go into a business, you’ve probably seen a lot of businesses on the inside at this point, what is the low hanging fruit that you see over and over again? What is the systems mistake that people are making that most of us have?

Alaia Williams: People have systems in place, whether they realize it or not. They either have the wrong systems for their business, or they’re not utilizing them fully. People aren’t consistent with the marketing. It’s choppy. They’re doing it. They’re on social. They have email lists, but they’re not consistent. They don’t have a plan. That’s one thing that no matter what system I’m going in to help someone with, we always usually end up swinging back to marketing, too.

Landon Ray: We had this long history, like traditional marketing was done in campaigns, so people think of, like I’m gonna run a marketing campaign, and a campaign has a start and a finish. There’s still a gap in understanding, often, that that’s not actually how it’s done anymore. You may run a campaign, but fundamentally a campaign is in support of a marketing system that’s gotta run all the time, right?

Alaia Williams: Yup.

Landon Ray: So, you’re helping people install those kind of systems in their businesses?

Alaia Williams: Absolutely.

Landon Ray: Yeah, and where does that start? What is the basic bare bones systems look like that you install?

Alaia Williams: The main thing that I want to make sure that everybody who works with me has is some kind of email marketing system, that they’re building a list. Social media changes, but if Facebook goes away tomorrow, at least you have a way to reach out to every customer, or potential customer. So, I always try to make sure they’ve got something in place for email, at the bare minimum, and the rest we can build based on their goals, and their audience, and where they want to go.

Landon Ray: Cool, so what are you learning now? What’s your own cutting edge? What are you struggling with?

Alaia Williams: I really want to get smarter about Facebook ads. I have a basic knowledge, but I want to get more into custom audiences and things like that. They’re so powerful, and now that I’ve expanded my business from services to products as well, I think that there’s a lot more opportunity for me with Facebook ads.

Landon Ray: Yes, for all of us.

Alaia Williams: Yes.

Landon Ray: If you could imagine, 20, 30 years down the road, looking back, what is the thing that you would like to have built? What would you like your legacy to be?

Alaia Williams: I think that’s where the Entrepreneur Connection is really the heart of what I do. I really like fostering those connections, and helping other entrepreneurs feel like they’re not alone in the journey, because that’s how I felt in the beginning, and I know I felt frustrated, like I wasn’t gonna be able to succeed, and it wasn’t true, but I just had no one to bounce ideas of off. I didn’t have a community. I didn’t have support, and so, I’d like to look back and have people say all these things about how I connected them with their new best friend, or a great business partner, or something like that, a relationship that caused them to have a light bulb moment, or foster some big change in their life. Whenever I hear those stories from people, that’s my favorite thing, so, I just want to do more of that on a grander scale, and really help small businesses grow, because I know what it feels like to feel alone when you’re growing a business.

Landon Ray: And lastly, we’ve called this thing the Modern Ontrapreneur. We’re trying to uncover what the unique opportunities, and maybe the unique responsibilities are for entrepreneurs today. What do you think that is?

Alaia Williams: Well, from my vantage point with working with entrepreneurs, it’s stepping more into that CEO or leader role, and getting out of the leads, letting go of control, delegating. It’s an ongoing struggle with entrepreneurs, but when I see people tripping up, that’s usually what’s causing it. Same with me. Whenever I’m tripping up in my business, it’s like I’m doing too much. I’ve got my hands in too many things. Let go, delegate. So, that’s a big one.

Landon Ray: Alaia, thank you so much for being here.

Alaia Williams: Thank you.

Landon Ray: It’s our pleasure. Would you sign our wall?

Alaia Williams: Absolutely, I’d love to.

Landon Ray: All right, thanks.


Want more Modern Ontrapreneur Podcast?

Check out the previous episode featuring Andrew Warner of Mixergy.


About Ben Cogburn
As Ontraport’s Traffic Manager, Ben Cogburn spends most of his time in our parking lot. Just kidding, he’s our resident digital advertising guru. As a geology enthusiast, Ben graduated from the University of California, Santa Barbara with a degree in Environmental Studies. So to say that he likes rocks is an understatement. You can find Ben hanging out with his rock collection, playing video games or hunting down new figurines to add to the impressive display he has on his desk.