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July 22, 2025 21 mins

Think Instagram is just for influencers and avocado toast? Think again. In this episode of The Aspiring Solopreneur, we sit down with Sydney O'Brien, a rockstar Instagram strategist who built her business while juggling three kids under five and a military deployment (yes, really).

Sydney shares why most solopreneurs are talking past their dream clients, the mistake you're probably making with your hashtags, and how to stop letting engagement (or lack thereof) ruin your day. 

From easy tools for beginners to the secret behind getting real conversations started in the DMs, she breaks down Instagram in a way that’s actually doable and even fun.

If Instagram makes your eye twitch, this episode is your cure. Tune in and get ready to rethink your whole content game.

Being a solopreneur is awesome but it’s not easy. It's hard to get noticed. Most business advice is for bigger companies, and you're all alone...until now. LifeStarr Intro gives you free education, community, and tools to build a thriving one-person business.  So, if you are lacking direction, having a hard time generating leads, or are having trouble keeping up with everything you have to do, or even just lonely running a company of one, be sure to check out LifeStarr Intro!

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Episode Transcript

Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Carly Ries (00:00):
If you've been listening to the show, you know

(00:01):
that Joe and I are not Instagrampros. We're not even social
media pros. So in this episode,we're joined by the strategist
behind atsocially.yours.strategist,
Sydney O'Brien, to finally getanswers to all of our burning
questions. Do hashtags stillmatter? What actually works
works on Instagram now?
And how do you post withoutspiraling into an engagement

(00:23):
induced identity crisis? Sydneyshares the must know strategies
solopreneurs need to actuallyconnect with their dream
clients, batch content withoutburning out, and maybe even,
dare we say, enjoy usingInstagram. So whether you're
totally new to content creationor just tired of hearing
crickets in your commentssection, this one is packed with
clarity, laughs, and actionableadvice. You're listening to

(00:46):
the Aspiring Solopreneur, the podcast for
those just taking the bold stepor even just thinking about
taking that step into the worldof solo entrepreneurship. My
name is Carly Ries and my cohostJoe Rando and I are your guides
navigating this crazy butawesome journey as a company of
one. We take pride in being partof LifeStarr, a digital hub

(01:07):
dedicated to all aspects ofsolopreneurship that has
empowered and educated countlesssolopreneurs looking to build a
business that resonates withtheir life's ambitions. We help
people work to live, not live towork. And if you're looking for
a get rich quick scheme, this isnot the show for you.
So if you're eager to gainvaluable insights from industry
experts on running a businessthe right way the first time

(01:30):
around or want to learn from themissteps of solopreneurs who
paved the way before you, thenstick around. We've got your
back because flying solo inbusiness doesn't mean you're
alone.
So Sydney, Joe and I were joking offline with you
about, oh gosh, why would weever wanna have an Instagram
expert on this show becausewe're so good at it. The reality

(01:51):
is we're really bad at it. Andso when you came across my
inbox, I was like, oh mygoodness. Yes. So, listeners,
this is for you, but this isalso for Joe and I because we
have some work to do when itcomes to Instagram strategy.
So anyway, Sydney, welcome tothe show. We have so many
questions for you.

Sydney O'Brien (02:10):
I'm so excited to answer all of them.

Carly Ries (02:13):
Well, before we dive in, we have this new thing that
we're doing with guests that wethink is just really fun to do
to get to know each other. So wewanna ask you, what is the
wildest thing that's happened toyou as a solopreneur?

Sydney O'Brien (02:23):
Okay. It was actually like how I became a
solopreneur because I started mybusiness when my kids were six
months and two and four yearsold while my husband was
deployed and I was in a newcity. He's in the air force and
I didn't know anyone. And forsome reason, I decided, you know
what? This is a good time tostart a business.

Joe Rando (02:45):
Yeah. Brilliant.

Sydney O'Brien (02:47):
Perfect timing.

Joe Rando (02:49):
Years ago, we had kids like that, you know, close
together and it's nuts. It'snuts. That third one just like
sent everything toppling off thecliff. and I was there. I was
around, and it was anyway, youare crazy. Serious. You know,
certifiable.

Carly Ries (03:09):
Yeah. But it's a star and a rock star too.

Joe Rando (03:12):
Yes. It worked.

Carly Ries (03:14):
It worked. It did.

Sydney O'Brien (03:16):
It worked out well in the end.

Carly Ries (03:18):
It did. And that's why we have you on today. So we
have so many questions, I'm justgonna kinda do the questions
that I personally need to know,and I think a lot of our
listeners can relate. How cansolopreneurs better identify and
speak directly to their dreamclient through all the social
content and actually reach whoyou need to reach on Instagram?

Sydney O'Brien (03:42):
The best way to do that is by talking to your
people. Like first knowingexactly who that is. niching way
down and then talking to themand kind of regurgitating their
words back to them in yourmessaging. Because the thing you
really wanna share that's gonnagrab attention is those anxious
thoughts that your ideal clientor customer has that's keeping
them up at 11PM when they sobadly wanna go to sleep but

(04:05):
they're worrying about this onething. That's what you wanna
talk about in your content.
Because they'll be like, oh mygosh, that's me. I know this
person can help me with that.

Carly Ries (04:12):
Yeah. good point. And it's funny because is there
any like targeting? Do hashtagsstill work? Is there any
targeting that you need to do toreach these people?
Because I'm thinking Instagram,you have access to the entire
world. How do you make sure youraudience, even if you understand
them, how do you make surethey're the ones that see it?

Joe Rando (04:32):
Right. Yeah. Good question.

Sydney O'Brien (04:35):
So hashtags don't really work like that
anymore. They used to which wasreally nice. But Instagram is
moving more towards SEO, searchengine optimization. So it's
more about finding long tailkeywords.
Like for me, I could useInstagram strategy, like digital
marketing tips, things likethat. And also outreach is

(04:58):
really helpful if you can dosome outbound engagement with
accounts that are complimentaryto your business. So because I'm
an Instagram strategist, I couldfind an email marketing person
and comment on their account andtheir followers are also in my
ideal audience. So they'll seemy content as well.

Carly Ries (05:20):
Oh, that's smart. See, it's things like that where
that makes so much sense andthat's so logical. But for some
reason when I get down toactually put a post in place,
it's like, oh, all that goes outthe window. Hey, question
though. Quick question on that.So when you do go and you post
on that email marketing person'scontent, what do you
say, what are the rules,

Joe Rando (05:40):
like, for kind of engaging people in a way that
they're gonna notice you, butnot being overly salesy or, you
know, not looking like that kindof sleazebag that's coming in
and trying to, just selleverybody.

Sydney O'Brien (05:55):
Right. Yeah. That's always a concern. I
always try to, add value to thepost without, taking anything
away from it. So if someone'stalking about one I did recently
just the other day was anInstagram marketer shared why
she doesn't like email templatesbecause it takes a lot of your
voice away.
I was like, I'm the same waywith Instagram. I love the idea

(06:18):
of a template because it makeslife easier but it takes so much
of your voice away and that'swhat people resonate with. So I
was like adding to the contentbut not dismissing anything she
was saying and not being superover promotional.

Joe Rando (06:31):
Yep.

Carly Ries (06:32):
how do you get people to engage and comment and
everything?
so I actually stopped posting onmy personal account back in 2020
because I found that if I didn'tget a certain amount of
engagement, it would affect myday. And I'd be bummed out. And
then it was like, people weren'tcommenting on pictures of my
kids. And like, that's thecutest kid ever.

(06:54):
And then it was just like,that's ridiculous. My day should
not be dictated by this. So Ijust stopped even trying to get
engagement and then just stoppedposting. But for people that
need that engagement forbusinesses, how do you foster
continuous conversations, DMs,comments, the works?

Sydney O'Brien (07:12):
So it's partly the two biggest mistakes that I
see with this for people wantingengagement but not getting it is
like specifically asking for it.specifically being like, hey,
comment on this specific topicor what are your thoughts about
like this very specific thing.And also again, outbound
engagement, even just replyingto people's stories, the more

(07:34):
you give out to people inengagement, the more you're
gonna get it back. And it alsohelps nurture followers and
potential leads and things aswell.

Carly Ries (07:43):
Okay. So I keep seeing the comments and
everything. In terms of contentmix, reels, stories, posts,
like, what is working? Whattends to perform the best for
solopreneurs, obviously, who aretalking to you, anybody for that
matter?

Sydney O'Brien (08:02):
Sure. It really kind of depends on your
audience. Like right now, I'mseeing a lot more reach and
engagement on carousels when acouple months ago for me, it was
reels. So there's like a shiftthere. But I have clients who
are still their reels get somuch more reach and engagement
than their carousels do.
So having a good mix of both andthen stories are also really

(08:26):
great for just kind ofconnecting with your audience.
You can get some good engagementthere just showing behind the
scenes, like what you're doingwith your day, what you're
working on, that kind of stuff.But if you're really not sure, I
would always suggest checkingyour insights. You can filter
them by seeing what gets themost reach, what gets the most
engagement, and just focus onthose so you're not wasting your

(08:49):
time on things that you knowaren't gonna work.

Carly Ries (08:51):
When I feel like there's so much pressure to how
I get get the best template touse, like for a person that's
never created a reel, it'sreally intimidating. Do you have
an editing software or anythingto make it really really basic
for people that wanna have animpactful video but are just
like like CapCut, like what tellme what to do.

(09:11):
Yeah. Help me. Help me.

Sydney O'Brien (09:14):
CapCut is definitely one of the best ones
because it is so easy to use andit's free. And there are a lot
of templates in there which makeit a whole lot easier so you
don't have to do any of theediting. You just upload a
couple clips and it'll do allthe editing and formatting and
stuff for you. Instagram alsocame out with their own editing
app called edits, which is nicebecause you can push it directly

(09:37):
to Instagram from the app. Andit'll also give you updates on
insights for your reels.
It'll send you notificationslike, this reel is doing this
percent better and reach yourengagement, which is interesting
to see. But I do like thatCapCut has templates and edits
doesn't. So definitely pointsfor CapCut there.

Joe Rando (09:58):
Isn't CapCut owned by TikTok?

Sydney O'Brien (10:00):
It is, yeah.

Joe Rando (10:01):
So one of things that made me nervous about it was
when they were talking aboutbanning TikTok, you would have
lost your editing app, right?

Sydney O'Brien (10:08):
Yeah.

Joe Rando (10:09):
I guess that's not really a big deal now. But boy,
I was looking at it and Iwent, Nah, I'm gonna use
Premiere.

Carly Ries (10:16):
Yeah.
Well, so let's say there's a person listening and
they're like, okay, I'm gonnacheck out CapCut. It's free or
edits just to try to make itlook a little bit better. But
still there's a learning curve.It could take time. So we always
recommend that people batchtheir content and then schedule

(10:36):
it out so that they're noteveryday trying to figure out a
new thing to do.

Sydney O'Brien (10:40):
Absolutely.

Carly Ries (10:41):
How can a person do that with Instagram and make it
quality so that they don't getburned out?

Sydney O'Brien (10:48):
I always recommend batching because for
the same reasons. It kind ofdepends though. So the way I
batch, how I batch content formy clients and how I teach other
people to batch is you plan outyour whole marketing plan for a
month or so, however long youtypically do it. And then week

(11:09):
by week go in and create contentjust because trends are always
changing. How people consumecontent is different.
You don't want to batch too muchand then have it become not
relevant even though you'reputting time and effort into it.
So have that full marketing planso you have the buyer's journey
outlined with your content. Soyou can still lead people to buy

(11:31):
by the end of it, but also kindof break it down. It's also more
manageable too if you don't havea whole bunch of time to just
sit down and create, like, anentire month's worth of content.

Joe Rando (11:41):
Can I ask a dumb question?

Sydney O'Brien (11:44):
Of course.

Joe Rando (11:44):
That's My specialty when it comes to anything
related to social media. So youjust said to have your buyer's
journey mapped out. And I knowwhat a buyer's journey is. I
think most of our listeners havethe concept. But how does that
work in the context of socialmedia where you're posting and
people are seeing it from alldifferent aspects?
Are you just resonating withthis particular post resonates

(12:07):
with this person at thisparticular point in your buyer's
journey? Is that is that how itworks?

Sydney O'Brien (12:13):
Yeah. So the way I teach it, I've created five
steps to sales on Instagram likeframework. And it's growth, so
you have the right followers,engagement, connection, trust,
and then promotion. And I willdo a couple of posts for each
step so that it's getting seenby people and then it leads up

(12:34):
to a launch or a sale orwhatever it is that I'm
promoting. So yeah, it is hardto kind of meet everyone where
they're at. I just focus on mypersonal business plan and go
around that. Okay. So you've gota group of people that see the
first one, get brought along.Some people are seeing it in the
middle and maybe going, I don'tget it. Or, you know okay. Good.

(12:57):
that just clears up so much.Thank you.

Carly Ries (12:59):
Well, so we were talking about batching all of
your content and everythinggoing in on a weekly basis, but
user generated content or peoplecreating the content for you
that you could share. I mean,how can people encourage that so
not all the pressure is on themto keep creating content?

Sydney O'Brien (13:17):
Mhmm. That can be a little tricky. The best way
to do it is kind of incentivizeit honestly. make it clear like
kind of they get something outof it as well. I ran a challenge
a little while ago and I got abunch because I had a bingo card

(13:37):
for it and people could beentered to win a prize.
And part of it was creatingcontent and tagging me in it as
like a collaborator. So it wouldshow up on my feed as well about
them interacting with thechallenge, showing their
insights and things like that.So I got reach and visibility
for it for me, but they also getprizes for them.

Carly Ries (13:56):
Alright. I'm, taking mental notes on all of this.

Joe Rando (14:01):
Well, it obviously depends on your audience. Right?

Sydney O'Brien (14:04):
Very true.

Joe Rando (14:05):
If you had an audience of attorneys, you know,
high powered attorneys, theyprobably wouldn't be going for
the bingo card contest. But withthe right group of people, it's
a brilliant idea.

Sydney O'Brien (14:16):
Yeah. Yeah. It's definitely gonna depend on the
industry.

Carly Ries (14:19):
For people that have a bunch of content and they're
like, yeah, I have all of this,but they aren't really seeing a
lot of results, is there a wayto do a content on it on
Instagram and how should peoplego about that to identify gaps
and what's working and what'snot?

Sydney O'Brien (14:33):
For sure. You can look at the benchmark rates
for insights like if you're notgetting, I think it's a 3%
growth for your account for amonth that's like below average.
So you can focus on trying toget more followers. A great way
to do that right now is if youhave the trial reels feature.

(14:53):
That's a really good way to getmore followers because Instagram
automatically shows your contentto people that don't already
follow you but are interested inthe topics you post about.
So you could do more of those.If your account gets around 5%
engagement, that's average. Soit's actually a lot less than
people would expect. If you aregetting DMs for sales or getting

(15:19):
clicks to your website, you'redoing better than average. The
conversion rate for mostInstagram posts for promotional
content is 2%.

Carly Ries (15:27):
It's funny because I as a marketer, those numbers
sound pretty normal, but I canimagine if there's just random
solopreneur and it's like, what?Those are the numbers?

Joe Rando (15:36):
Yeah. all that work and all that post and all that.

Carly Ries (15:40):
Yeah. Exactly. Well, so it can seem like a lot for
people. They're running theirbusiness, and so they have to
worry about other areas, areasof marketing, but their
operations, processes,everything. So when should it
would you think a solopreneurshould consider hiring a
freelancer to help with this ora contractor?
Or even partnering with anagency instead of taking it all

(16:03):
on themselves?

Sydney O'Brien (16:04):
I think a lot of it comes down to like most
decisions budget and time. ifyou just don't have the time,
it's definitely worth lookinginto some kind of outsourcing,
whether it's a membership or oneon one work or an agency. But
also your budget is obviouslygoing to influence that as well.

(16:29):
The biggest thing I would say ifyou're going to outsource
completely is make sure you havea one on one call or
conversation with someone firstto make sure they're a good fit
for you.

Carly Ries (16:40):
And what should they be looking for? Like you say
good fit, but is it personality?Do they understand your brand?
are there any red flags thatpeople should look out for?
Because I've heard time and timeagain that people are like, oh,
I had a great discovery callwith this agency and then FWOP.
They seem like a greatcontractor to work with, FWOP.
And that they just, they'rewasting so much money.

Sydney O'Brien (17:02):
Yeah. I would make sure they understand your
brand and your values becausethe way social media works is
your messaging has to be spot onand it has to be in your voice
for it to hit home with youraudience. So the person you work
with really needs to understandthat, and I would also ask to
see like a portfolio and thingsto make sure that they're doing
that for other clients as well.

Carly Ries (17:21):
Is it common to speak to current clients? to be
like, can I talk to one of thepeople you're currently working
with? Or does that not reallyhappen?

Sydney O'Brien (17:32):
It hasn't really happened in my experience, but I
also like when people have acall with me, I give them a
packet of information. It hasreviews and insights and
information from other clients.So they do have all that
information. But if that's notprovided to you and you're
looking to hire someone, I wouldcertainly ask.

Carly Ries (17:50):
Okay. Yeah. Because like you said, there's just a
lot to think of.

Sydney O'Brien (17:54):
Yeah. Actually That's a big decision.

Carly Ries (17:56):
When there's, like, done for you packages and all of
that stuff. Joe, I think thoseare a lot of my questions that I
had that I just needed to getthis out there. Do you have any
that I've missed?

Joe Rando (18:07):
Well, no. I think just to expand on what you said,
I think what is implied in thislast exchange was that it really
has to be you that's comingacross. Now whether it's
actually you writing the wordsin order that's gotta be coming

(18:29):
from you somehow. So is thereany thoughts you have on how if
you're having someone help you,how do you kind of convey you to
them in a way that lets themauthentically represent you when
they're doing this work? Or isthere some kind of back and
forth that should go on in orderto make sure that it's all on
target?

Sydney O'Brien (18:50):
So normally, there's a discovery call and a
whole bunch of at least whenpeople hire me, there's like an
intake form where I look over,they answer questions about
their values, their mission, allof this stuff. I'll do deep
dives into their website to lookat their copy there. I'll have

(19:11):
them write other paragraphsabout what they do just off the
cuff and have a conversationwith them to hear what they talk
like. It takes a little while toget their voice and messaging
right, but it is just such animportant part.
It's definitely worth the formsand the phone calls to get
there.

Joe Rando (19:30):
How is your Boston?

Sydney O'Brien (19:33):
My Boston?

Joe Rando (19:34):
Yeah. if you're channeling me, I grew up outside
of Boston. So people are wickedsmart.

Sydney O'Brien (19:40):
It's Yeah. I'm from New Hampshire, so it's not
too bad.

Joe Rando (19:42):
You've got that. You don't sound like New
Hampshire.

Sydney O'Brien (19:48):
No. because my husband's in the air force, we
move around a lot. yeah. We hearall the all the accents.

Carly Ries (19:56):
A lot of us, they can master it.
Well, it sounds like you'vehelped so many people people
find success on Instagram. So weask all of our guests this
question, what is your favoritequote about success?

Sydney O'Brien (20:08):
I really like this one that Serena Williams
said. She said, success is doingthe things most people don't
have consistency for, which Ifeel like really applies to
being a solopreneur because somuch of it is just being
constant and being consistent soyou can get those results that
you want.

Carly Ries (20:24):
Thanks for tying it back to the audience. Much
appreciate it. Well, Sydney,this has been great. Thank you
so much for answering all of ourquestions. If people wanna learn
more about you, where can theyfind you?

Sydney O'Brien (20:35):
Absolutely. My Instagram is a great place. My
handle is atsocially.yours.strategist. I
have a podcast called mompreneurmastery. I also have a free
content planning, five daychallenge to help you plan a
month of content in five dayscalled Plan it Post it Profit.

Carly Ries (20:57):
All of that will be included in the show notes. And
thank you so much for coming ontoday.

Sydney O'Brien (21:02):
Thank you so much for having me.

Carly Ries (21:04):
Yeah. And listeners, thank you so much for tuning in.
As always, please leave thatfive star review. Subscribe to
this show on your favoritepodcast platform including
YouTube. Share this episode witha friend, and we will see you
next time on The AspiringSolopreneur.
You may be going solo inbusiness, but that doesn't mean
you're alone. In fact, millionsof people are in your shoes,

(21:25):
running a one person businessand figuring it out as they go.
So why not connect with them andlearn from each other's
successes and failures? AtLifeStarr, we're creating a one
person business community whereyou can go to meet and get
advice from other solopreneurs.Be sure to join in on the
conversations atcommunity.lifestarr.com.
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