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July 30, 2025 38 mins

On this episode of Oh Frac!, host Adir Ron sits down with Jack Oliphant—endurance athlete, former CBSi/Vox/Acast rain-maker, and self-proclaimed “fractional generalist.” From finishing an Ironman to shepherding multimillion-dollar ad products, Jack now blends RevOps, sales leadership, and operational strategy for seed-to-Series D startups. Tune in for a candid look at why CRM is a fractional’s best friend, how LinkedIn can both fuel and fool your pipeline, and the drama of a cap-table recap gone sideways. Whether you’re a founder weighing fractional talent or an exec eyeing the leap yourself, Jack’s hard-earned lessons on pacing for the long game will leave you ready to race.

 

Key Takeaways:

* Endurance training parallels fractional life: dream → train → race mindset

* “Fractional generalist” = RevOps glue across sales, marketing & CS

* CRM first, always—start tracking relationships on day one

* HubSpot is now a legit enterprise rival to Salesforce for many scale-ups

* Weekly Loom video updates keep clients aligned & personal

* Partnerships (e.g., Domestique) expand reach without sacrificing solo freedom

* Cap-table recaps: emotionally charged but rich in board-level lessons

* Retainer-based scopes beat hourly billing for strategic work

* Build your ICP early to filter ideal clients and engagements

* Fractional market likely to grow beyond 10 % of U.S. workforce in 5 years

 

Chapters:

00:00 Welcome & Jack’s intro

03:30 Ironman mindset meets fractional work

08:00 From CBSi → Vox → Acast → solo founder

12:30 Million-dollar ad product & risk tolerance

16:30 “Fractional generalist” explained + LinkedIn hacks

21:00 CRM deep-dive: HubSpot vs Salesforce

25:30 Partnering with Domestique for bigger wins

29:30 Frac’d-Up Moment: recapitalization drama

34:00 Quickfire round: myths, tools, dream clients

38:30 Final advice & where to find Jack

 

Jack Oliphant’s LinkedIn: https://www.linkedin.com/in/jackoliphant/

Jack's website: https://www.oliphantstrategies.com 

Adir Ron’s LinkedIn: https://www.linkedin.com/in/adir-ron/

 

Keywords

fractional leadership, RevOps, CRM, HubSpot, Salesforce, startup growth, endurance mindset, Ironman, LinkedIn strategy, cap-table recap, revenue operations, podcasting, fractional CMO, fractional executive

Mark as Played
Transcript

Episode Transcript

Available transcripts are automatically generated. Complete accuracy is not guaranteed.
(00:00):
I'm sure that other people who have worked across the portfolio as well would attest to that.
So, I only lasted about a year before jumping head first into podcasting, which is really something that I'd seen at Vox Media as well.
Still today, you can just go and kind of do whatever you want, right?
Like, I saw another joke meme, for instance, where somebody called this out, uh, on, uh, X, Twitter, and then made himself the CEO of LinkedIn.

first off, um, Frack or Fiction (00:29):
Um, "Fractionals need to specialize in one industry to be successful."
Yeah.
I will also plug, um, Weekly Looms, um, and this was something that I picked up with Domestique, uh, which I think is a great way to relay information back to your partners.

(00:49):
Welcome to Oh, Frack!, the podcast where top Fractional Leaders share their wins, struggles, and stories from the trenches, hosted by Adi Aron.
Welcome to Oh, Frack!, podcast where we dive into the world of fractional leadership, the wins, the struggles, and everything in between.
Uh, I'm your host, Adi Aron, and I'm a Fractional CMO, and today we have with us Jack Oliphant.

(01:17):
Jack, welcome.
Thank you.
Happy to be here.
Happy to have you here.
Um, so a bit of background about Jack, our guest for today, uh, from CNET, and, and, and CBSi, Vox Media, Acast, Jack built his chops in digital media and enterprise sales, and podcasting, um, before turning founder, um, and now operates in a sharp, full stack fractional, uh, exec.

(01:46):
Um, Jack blends rev ops, sales leadership, operational insights into a single streamlined offering, helping early, early stage companies make smarter GTM bets.
And, he's also literally Ironman.
.00000000001455So, so Jack, um, welcome and let's, you know, let's kick it off. 19 00:02:10,359.00000000001455 --> 00:02:18,110 Um, so you finished an Ironman, um, you finished multiple marathons, um, you launched your own company.

(02:18):
.0000000000291What's, you know, what's, what's a skill from endurance sports that is very relevant, uh, and maybe in a surprising way, uh, relevant to fractional work?
Uh, yeah, that's a great question.
Um, I actually put together, um, my own format of crawl, walk, run, um, but I actually relayed it back to my own triathlon and endurance, uh, training, you know, from a perspective of dream, train, race.

(02:53):
Uh, so, you know, there's a lot of mental, uh, attitude that goes into endurance training, um, as well as, uh, marathon, and triathlon, and Ironman competitions, um, so that- Yeah.
dream bucket is, uh, is really important to get your mental attitude right.
And then from a training perspective, uh, there's a lot of hours, uh, there's inherently a lot of risk, uh, with running your own shop, especially from a fractional basis.

(03:22):
Um, so, you know, the training and the number of hours I think correlates, uh, really well into the model.
And then finally, racing.
Um, you know, actually implementing it with clients, um, getting feedback from clients, and, uh, yeah.
I mean, I think there's a ton of different lessons that you can learn from endurance sports, or just sport overall.

(03:44):
.0000000000291Yeah.
That, uh, that, uh, that very much resonates.
I al- I also think that, um, playing the long game, um, especially, you know, when we're talking about, you know, uh, uh, Ironman competitions and marathons, you're not sprinting.
You need to learn to pace yourself and plan ahead and foresee rough patches, and, like, keep running even after you are, you are tired.

(04:14):
And, yeah, I, uh, I, I, I can definitely see the correlation now, uh, as you were speaking.
It materializes, uh, right in front of me.
Yeah, absolutely.
I mean, with running any business, um, you know, kind of the first jump into it is super scary, um, and especially from, like, a freelance or consultant perspective.
You're not sure how long you're gonna be doing it most times, right?

(04:35):
Uh, people kind of dip their toes into the waters.
But I've, uh, especially over the last year and a half or so, um, really projected long term, uh, growth and business, um, so that's what I love to help clients and partners with as well, um, focusing on the long term, uh, rather than these, like, short-term wins or gains.

(04:57):
Um, you know, every project and every partner is a little bit different, um, but, you know, the ones that I really love working on are, are focused on, you know, a couple years out rather than the next 30, 60, 90 days.
Um, so long term growth through operationalization is what you'll find on my website.

(05:17):
Um, so that kind of leads me to, you know, the next question.
What's, you know, what's your story or how
Because I like silly humor, how I like to call this corner is How the Frack Did You Get Here?
Um, so, you know, from, from CBS Interactive, from, you know, from Vox, Vox Media, from Acast, um, all the way to being a fractional generalist.

(05:40):
What does that even mean?
How does that look like?
Tell us a bit
Yeah, absolutely.
So, you know, I really started, um, my career in digital media, uh, and publishing at CBS Interactive.
Um, so at the time, they had owned a portfolio of websites, including cnet.com, um, which was and probably is still the largest tech news and reviews website.

(06:06):
Um, so I got promoted.
I moved across the country.
I represented, uh, some of the largest accounts at the company.
.0000000000582Um, so really got hands-on experience with, uh
um, managing many teams internally, so everything from, uh, client success to, uh, digital operations, to the finance team, to our marketing lead contacts.

(06:32):
Um, and I think that's really where I had my first interaction with revenue operations, um, even though they weren't necessarily calling it rev ops at the time.
Um, I was- Yeah.
managing 5 internal teams in New York City, as well as 2 of the largest accounts at the company.
Um, so both from an internal and external perspective, I was able to gain a lot of experience at a multinational enterprise conglomerate.

(06:55):
Um, so, you know, I think that I was ready for the next step in terms of another promotion in my career.
And as you work at enterprise, large corporations, that path is kind of dictated for you in terms of who's there and whether they're gonna promote internally or hire externally.

(07:15):
Um, so I- Right.
could see just kind of the limited number of slots of folks.
Um, so I ended up taking an ex- external, um, position in order to get that next promotion.
Um, Vox Media was a medium-sized publisher at the time, and, uh, self-described as turbulent by the CEO.

(07:35):
Um, so it was definitely an interesting time to be at Vox.
Uh, I'm sure that other people who have worked across the portfolio as well would attest to that.
So, I only lasted about a year before jumping headfirst into podcasting, which is really something that I'd seen at Vox Media as well.
Watched a team of about 2 to 3 headcount go to almost 10 within 12 months.

(08:00):
So, I was able- Wow.
.0000000000582to identify that emerging platform, um, and channel that was podcasting at the time.
Um, so then I jumped into Acast, um, had a ton of success, and that success was really what led me into, uh, starting my first, uh, you know, go at independent contracting, consulting, freelancing, whatever you'd like to call it.

(08:24):
So, um, I actually built- So, how, how did that work?
Well, so I built and sold, um, an ad product, uh, with my team internally, and then rolled it out to multiple markets.
By the end of, uh, my tenure at Acast, it had actually sold over a million dollars in 3 markets.
Nice.
Um, I also had a huge amount of success in, in 2020.

(08:50):
Ended up being approximately 35% of the Americas team revenue.
Um, so, you know, that allowed me to, to take a big risk in terms of starting my own shop.
Um, and this is something that I tell a lot of folks that are either getting into, uh, independent consulting, freelancing for the first time, um, is that if you can mitigate that risk by taking side projects with your full-time employment so you're not giving up things that are important, like healthcare, a steady paycheck, a 401, et cetera, I highly recommend that.

(09:26):
Um, so, you know, if you can kind of dip your toes in the water without necessarily taking- Yeah.
the full headfirst dive in, um, then that's a conversation that I consistently have with folks that are looking at a first time into freelance consulting.
Um, but I definitely have a higher risk tolerance, uh, I'd say, than, than a lot of folks, um, which is what drove me, uh, into starting my own business.

(09:54):
Um, and there's actually a, uh, a funny economics, uh, fact.
I don't know if it's still a fact, because this was many years ago when I was studying econ in college, um, but- Mm-hmm.
Okay.
there are only 2 things that correlate with entrepreneurship.
It's either having a safety net, meaning that multi-generational wealth, et cetera- Yes.

(10:18):
um, or your parents were entrepreneurs.
Um, so my mom actually ran a small business, uh, throughout my entire life for music and tutorial, um, and I think that exposure to risk also, uh, lends itself to my own risk tolerance as well.
Interesting.
I never, I, I had never heard of that before today, and um, uh, my dad was a small business owner, um, so I can, uh, I can relate.

(10:47):
Uh, the numbers add up so far.
Yeah.
Um- Anecdote of 2 here.
Uh, I'll, I'll add it to my, uh, roster of questions and then I'll start asking the next guests that, "What did your parents do-" Yeah.
uh, that led you to be, to become a fractional"
so- For sure.
Correlation not causation, but those are- Exactly.
the only 2 things that correlate with becoming an entrepreneur.

(11:11):
Interesting.
Um, so what's, what, what's, you know, y- why do you call yourself a fractional generalist?
That's a question that I, uh, I was waiting to ask, to ask.
Yeah.
Uh, it's, it's a little bit of a, uh, not a, not a joke necessarily but just a play on the fact that I've done a lot of different things over my career.

(11:35):
I've worked at different companies, um, even, you know, running my own business I've taken a lot of projects.
I've, uh, worked in a lot of different capacities with different teams, um, that are all the way from like bootstrap, uh, seed, kind of friends and family, all the way through like late stage Series D exit.

(11:56):
Um, so you know, kind of one of my big skillsets is to be able to come in and, and identify, uh, areas for improvement and long-term growth.
Um, so with the fractional generalist, um, tagline on, on LinkedIn, I think it also drives people to ask, like, "What do you actually do?"

(12:19):
Right?
Yes.
And so it's definitely a hook a little bit in order to engage people, um, to try to spur the conversation. 115 00:12:27,959.0000000001164 --> 00:12:42,419 I would say for the most part, uh, especially in the last 6, uh, to 12 months or so, um, I've been solely focused on revenue operations, which I think does lend itself to that generalist title, right?

(12:42):
You're working across multiple different teams including sales, marketing, and CS in order to help drive the revenue function for the overall company.
.0000000001164Um, so yeah, I mean, I think it's, it's also you need to have a little bit of fun out there, um, in your day-to-day. 118 00:12:59,699.0000000001164 --> 00:12:59,739 Yeah.
Exactly.
And LinkedIn, I think, is a great tool but also a place to not take yourself too seriously.

(13:06):
.00000000011642Um, you know, there's a subreddit all about that if you want a good laugh, LinkedIn Lunatics is, is, is quite a, quite a place on the internet.
LinkedIn Lunatics.
I'll remember that one for later.
Right.
.0000000001164I'll check it out.
Um, I do remember, um, I read, uh, uh
So an- an anecdote on LinkedIn Lunatics, I read a story about a guy who was getting, um, contacted, um, constantly with like AI job offers, so he built a profile for his phish, uh, and he called it-

(13:41):
like Sea Bass something, and the picture was, the profile picture was a fish, and he built like an actual resume with the company names and the titles but in the actual details.
So he was software developer at Apple but within a phish tank writing phish code.

(14:04):
So it's like if you, if a person actually takes literally more than 5 seconds to go over his profile, he would realize this is a joke.
But he kept getting, like because he built like resume of working at Apple and Microsoft and Google and all those companies in software development, he was getting like over 50, uh, uh, job offers every single day for his phish profile. 132 00:14:26,439.0000000001164 --> 00:14:28,98.99999999988358 Um, so yeah. 133 00:14:28,98.99999999988358 --> 00:14:32,139 I mean, there's so much to unpack with LinkedIn right now.

(14:32):
Yeah.
Especially from a revenue operations perspective and, uh, even just like validation and verification, um, because still today you can just go and kind of do whatever you want, right?
Like I saw another joke meme for instance where somebody called this out, uh, on, uh, X, Twitter, and then made himself the CEO of LinkedIn, right?

(15:00):
So like, the fact that you can still and kind of like manually input all these different things without a real, you know, verification, uh, process is, is very interesting, especially when, you know, a lot of B2B enrichment and prospecting, uh, tools are using LinkedIn as its source of truth, right?

(15:20):
.9999999998836So- Exactly. 139 00:15:21,598.9999999998836 --> 00:15:37,259 if you're still taking the source of truth as manual input, like there's probably a variance of what's actually true versus what people are posting online, um, which is always the case in, in every different community, um, but yeah.
I mean, LinkedIn is a, is a crazy place.
I've been a LinkedIn premium member for over 10 years at this point, um, so it's been a long part of my career path and trajectory.

(15:48):
Yeah.
Um, I mean, I still remember when they bought lynda.com, um, and then eventually rebranded it LinkedIn Learning. 144 00:15:56,699.0000000001164 --> 00:15:57,598.9999999998836 Um, so- Yeah. 145 00:15:57,598.9999999998836 --> 00:15:58,640 Wow, that was a long time 146 00:15:59,137.99999999988358 --> 00:16:00,419 That was a long time ago.
.00000000011642I know. 148 00:16:01,199.00000000011642 --> 00:16:03,079 So- Yes, I remember those days.
I had a- Yeah.
.9999999998836Lynda, uh, subscription back then.I did too. 151 00:16:07,310.9999999998836 --> 00:16:10,544.0000000001164 Um, that's actually where I first learned Excel.

(16:11):
Uh, that was a big miss by my college, as much as I, I loved CMC where I, where I went to school.
Um, we learned, uh, like, you know, econ, uh, stats software, right?
.0000000001164Econometrics- Yeah. 155 00:16:25,391.0000000001164 --> 00:16:26,571 is what it's called.
.00000000011642Um, but the software is solely for academia. 157 00:16:31,151.00000000011642 --> 00:16:34,231 There was no real life app- application for it.

(16:34):
Um, so- Yeah. 159 00:16:35,891.0000000001164 --> 00:16:43,752 when I got into one of my first jobs, even before CBS, I learned Excel 8 to 12 hour course on lynda.com.
Um, so yeah, it's a throwback for all, all the software nerds out there.
.0000000001164Uh, it's interesting though that you, you were talking about LinkedIn and you used the phrase "source of truth," and I feel like that is a very rev opsy, uh, phrase. 162 00:17:01,891.0000000001164 --> 00:17:02,771.9999999998836 Yes. 163 00:17:02,771.9999999998836 --> 00:17:03,191 Um- You got me.

(17:03):
in, in essence, uh, it's a very rev opsy perspective, um, of, you know, you need one source of truth.
That's typically the CRM, that's typically, like, where everything, you know, is built upon, everything comes out of, and, and, like, where you spend your, most of your days in a way. 166 00:17:23,521.9999999998836 --> 00:17:24,50.999999999883585 Yeah. 167 00:17:24,50.999999999883585 --> 00:17:27,191 I mean, you're, you're hitting the nail on the head.

(17:27):
I'm a big-
.9999999997672CRM proponent. 170 00:17:29,630.9999999997672 --> 00:17:34,130.99999999976717 Um, you know, I use HubSpot, I'm a HubSpot admin. 171 00:17:34,130.99999999976717 --> 00:17:37,130.99999999976717 Um, I've also been with- Same here. 172 00:17:37,130.99999999976717 --> 00:17:38,451 HubSpot for many years.
I mean, I remember when they were still an email marketing tool solely as like a Mailchimp competitor.
Um, and now, you know, they're a full marketing automation platform, plus CRM, plus, I mean, customer service hub.

(17:53):
.9999999997672Like, I mean, there's, there's so much that HubSpot can do, um, at this point. 176 00:17:57,831.9999999997672 --> 00:18:16,591 Um, but, you know, I, I recommend this a lot, and might get into some of your, um, other questions later on, but like, I run an, a workshop, uh, that I'm actually doing with Hu- a HubSpot community coming up in the next couple of weeks, uh, the ABCs of CRM and ICP- Hmm.

(18:16):
.00000000023283for small business owners.
.9999999997672Okay. 179 00:18:18,610.9999999997672 --> 00:18:22,051 Um, so there's a bunch of different tools out there.
Uh, you don't, you don't have to necessarily use HubSpot, and especially for what you need in terms of a small business, or even like, seed to series A, uh, you might be able to use a different tool.
Um, but I would say that like from, if you ask most revenue operations folks, like Salesforce and HubSpot are gonna be the 2 recommended tools, just depending on where you are as, uh, maturity of a company.

(18:47):
.00000000023283Um, and- Exactly. 183 00:18:49,291.00000000023283 --> 00:18:57,871 I think for like the first time, uh, in the last couple of years, HubSpot is a real competitor to Salesforce on an enterprise level.
Um, so, uh, it's, it's gonna be a very interesting landscape over the next, uh, 3 years, especially in terms of how AI and incorporation of AI, uh, just competes within the 2 major duopoly at this moment, right?

(19:17):
I'm, uh, I'm team HubSpot all the way, by the way.
.00000000023283Um- Sure. 187 00:19:21,311.00000000023283 --> 00:19:21,391 I'm team-
I have, I have- Me too.
customers that, that are, uh, some, some customers that are Salesforce, and literally every single CRM conversation, I'm like, "Are you sure we can't migrate to HubSpot?"
It'll be so much easier, you know, we'll have s- like, we'll have so much more fun.
It's just like- Yeah.
.99999999976717such a different environment to work in, in a Salesforce environment than a HubSpot environment.

(19:43):
There are still some serious pros for Salesforce if you're a late stage enterprise, um- Of course.
or even like, you know, on the verge of IPO, if you're a series D or raise, you know, hundreds of millions of dollars and have a lot of data.
Um, but at the same time, I think that, uh, HubSpot can be the solution for a long part of that journey, if not at this point, for the entire time.

(20:09):
Um, but there are still some, some very serious pros, um, for, for Salesforce.
.99999999976717And actually just while- Yeah. 198 00:20:16,130.99999999976717 --> 00:20:26,899 I'm plugging enablement, uh, different, um, tools, Salesforce's Trailhead is a really good enablement tool where you can go and learn the platform really well.
Um, so HubSpot has their own HubSpot Academy, um, so if you are interested in learning, you know, more about the different tools, uh, then each has their own respective, uh, enablement platform.

(20:41):
Um, so let's, you know, let's talk a bit about how you, you know, if, if you're willing to share a bit about projects that you're doing as, you know, as, as fractional RevOps, and, and I'll kind of tie it to our next question, uh, which is, what's your, or what's a recent, uh, fracked up moment that you had as a RevOps, fractional RevOps leader?

(21:09):
Yeah.
Uh, you know, I'll plug, uh, Domestique, um, which has become a partner of mine.
I'm an independent contractor for them, um, as, like, a revenue operations consultant.
Um, so they're a larger firm out of, uh, the Denver area, but they're also based all over the place.

(21:29):
Um, right now I believe they have 8 full-time, uh, what they call pit crew, and then, uh, 40-plus Peloton members, uh, which are experts across the board just depending on whatever project that you might need.
So, you know, I have my own business, Uh, All Fun Strategies, but at the same time I think partnering with them has been an amazing opportunity, um, in order to get a more diverse selection of projects.

(21:54):
Um, so they're hiring for different roles and, uh, currently, um, so Domestique is a cycling, uh, reference.
It's the, uh, person who actually breaks, uh, win for the Peloton behind it, um- Okay.
so it, it's like kind of the leader of the pack.
Um, so definitely, you know, I, I resonate with a lot of, you know, their own, uh, internal, you know, company values and even the different nomenclature that they have, being a cyclist myself.

(22:25):
Um, but yeah, no, I mean, I think that they've been an amazing partner, um, and it's definitely allowed me to extend past my own, uh, network in order to, you know, pull from different projects that I might not have been able to access before.
So I highly recommend trying to build partnerships with either other independent consultants or, you know, agencies along the road, because, uh, there are a ton of, like, 4th spaces or online communities where you can start to, to grow your network and, and get those referrals from different folks that have, you know, other expertise, right?

(23:06):
So I already belong to a few of them, um, including, I think, where, you know, we had met, which was, uh, Nextplay.
.0000000002328Um, so, you know, highly 215 00:23:15,639.0000000002328 --> 00:23:17,439 I will plug Nextplay too.
Mm-hmm.
I've really loved that community.
Uh, the friends of Nextplay has been amazing.
I've also raised my hand in terms of office hours, um, so I run, you know, uh, office hours for anybody that's interested in getting into, uh, fractional consulting for the first time.

(23:34):
I have resources for folks as well, including like a, a tech stack recommendation for a solopreneur or small business.
Um, so yeah.
I mean, I think that there's a ton of ways that you can get projects, and, uh, one interesting one, uh, currently is my engagement with Domestique.
Um, but yeah, coming back to the fracked up moment

(23:57):
Uh, so- Yeah.
We all have those moments, right?
Uh, it's, uh, it's definitely a learning curve in terms of, you know, going out on your own for the first time, but there was a project, it was a couple years ago, where I actually was a part of a potential recapitalization of a cap table.

(24:20):
Um, so- Okay.
it's a pretty new- You wrote to me about that.
Yeah.
Yes.
.9999999997672I was waiting for, for you to, to get to that story. 232 00:24:26,918.9999999997672 --> 00:24:27,959 Yeah.
It doesn't happen, uh, all that often, actually.
.00000000023283Recaps are, are 235 00:24:33,139.00000000023283 --> 00:24:38,831.9999999997672 I guess they're more common than they used to be, but for a long time it was basically never used.
Um, and it's a way to, um, essentially bring the cap table down to a couple of different investors, um, or- Right.

(24:47):
uh, individual stakeholders.
Um, but it's pretty dramatic so especially when you're dealing with, uh, founders or co-founders, uh, that have large stakes of equity in the company.
Right.
Um, so that experience with the board, with investors, with, uh, long-term co-founders was definitely an emotional moment throughout, uh, my fractional career, um, but it also taught me a lot too.

(25:18):
Um, so, you know, if you, if you've never kind of, uh, interfaced with boards or, uh, C-suite executives before, and I think that you end up doing it a lot more as a fractional person or a consultant.
Right.
.00000000023283Um, it's, uh, it's a lot of different, I would say, personality types, um, so just learning the different personality types and, and trying to put your CS hat on and, and be as friendly and, and welcoming as possible, um, but yeah. 244 00:25:52,139.00000000023283 --> 00:26:03,199 I mean, for those of you that aren't familiar with what a recap is, I, I encourage you to take a look online and, and see what that is because it is a lot of drama.

(26:03):
Um, but that was definitely a, a major learning, uh, moment in, in my fractional journey.What's, uh, what, what was your biggest takeaway from, um, you know, from that moment?
.00000000023283My biggest takeaway was the fact that co-founders have both a personal and professional relationship, especially for co-founders that have been doing it a really long time. 247 00:26:34,389.00000000023283 --> 00:26:53,758 Um, so, there's a lot of history that, like, if you're coming into a project for the first time and that company's been around for 4 or 5, 10, how many years, um, that you don't quite understand all of the different moments in time that this company has had, right?

(26:54):
they could've been sprinting for the last 24 months just trying to hit profitability, right?
They could be ten years, you know, old and gone through multiple rounds and a lot of different history that you just won't be able to catch up on, and trying to understand where the co-founders, and then also where the board is coming from is the biggest learning moment.

(27:20):
So like, trying to balance, like, where the co-founders are at as well as the board, um, if you are talking about a company that's taken investment. 251 00:27:31,389.00000000023283 --> 00:27:31,969 Yes.
That's, uh, it's a delicate balance act, um, in, in like finding yourself in that kind of seesaw or equation, um, and, and yeah, and walking away. 253 00:27:49,389.00000000023283 --> 00:27:51,029 it's definitely a learning moment.

(27:51):
.0000000002328I can see that, um, thank you for sharing that.
.99999999976717Yeah, absolutely.
So, maybe, uh, to light up the atmosphere a bit - Yeah, sure.
a little bit, um, we'll, uh, we'll switch over to our, uh, quick-fire round.
I'll ask you a couple of short questions.
Um, so first off, um, fraq or fiction?

(28:15):
Um, fractionals need to specialize in one industry to be successful.
Uh, friction.
Friction?
Okay.
Would you like to elaborate?
Uh, yeah.
.9999999997672I mean, I think as a small business owner, you have to know a lot of different things, um, so I think that you can have services that are very dialed in to an expertise. 267 00:28:42,349.00000000023283 --> 00:29:12,708.9999999997672 Um, you can also outsource a lot of the different things that you need in terms of support, um, going back to like, the tech stack recommendation, um, whether that's like bookkeeping or taxes or invoicing or things like that, but I do think that you need some type of holistic knowledge in order to like, really be a, a really successful, uh, fractional consultant, um, because when you come into a team, you aren't 268 00:29:12,708.9999999997672 --> 00:29:17,309 usually just servicing one stakeholder or champion, right?

(29:17):
You are working with multiple different stakeholders.
.9999999997672Um, so- Right. 271 00:29:21,708.9999999997672 --> 00:29:34,416 while I think it's really important to, you know, dial in your service or offering based on your expertise, I think that you do need a little bit more of a holistic background in order to be successful.

(29:38):
What's your number one tool in your toolbox?
The CRM.
The source of truth.
Yes.
Uh, I mean- And I would say HubSpot's, uh, from, from our conversation.
Yes.
I'm, I'm a HubSpot proponent.
Um, but kind of like I'd mentioned, there are a bunch of different tools that are out there that are great.

(30:01):
Um, Zoho comes to mind, um, but there's, there's a whole bunch of them currently, and there's new ones popping up all the time as well just because of AI and, and the new technology that's coming about in terms of data and enrich- enrichment and prospecting and sequences and all of this stuff.

(30:30):
I r- I heard really good things about, um, Adio.
Sure.
Um- That's also- I, uh, haven't-
on my list.
had a chance to- Uh
like, play with it too much, uh, but, uh, it looked like a very solid solution.
Yeah.
So the ones that- Out of the new contenders.
I vetted, um
A lot of people use Airtable as, like, a backend, uh, CRM just because it's more of their digital operations, uh, crux or tool.

(30:58):
Um- Yep.
I wouldn't consider that a CRM, but could you build out a CRM within Airtable if you're an Airtable expert?
Sure.
Probably, yeah.
Um, and I've heard people say that they're doing it.
So, uh, that came to the top.
Adio, uh, Folk, um, Pipedrive- I, I heard about Folk today.
Yeah.
Yeah.

(31:18):
For the first time.
Um, and then Zoho are the ones that I kind of vet, uh, in the workshop that I do, and then a couple of others actually came up a, a few times are HighLevel, um, and HoneyBook.
I didn't know HighLevel.
I'll check them out.
Um, okay.

(31:38):
Um- Yeah.
next question.
Um, w- what's
Describe your dream client versus your nightmare client.
My dream client is a 12-month commitment.
Um, so- I can relate.
Yes.
A long-term retainer partner is my dream client.

(32:01):
Um, so anything above 3 months really, um, but 6 to 12-month engagement where I could properly, you know, become an integral part of the team, uh, where they don't have to actually spend the money on a full-time, uh, hire, right?
So- or full-time employee.
Um, I think that's, like, you know, where my, uh, dream would be in terms of partners.

(32:28):
Um, really, you know, 3 to 6month engagement, um, i- and I, I could, you know, build out my ICP for you here.
But I think long-term partnerships, uh, versus, like, short-term gains, it just level sets the entire relationship, um, that it doesn't become just, like, kind of, like, how many minutes did you work, you know, this week?

(32:54):
.0000000002328Um, so, you know- Yeah. 319 00:32:55,639.0000000002328 --> 00:33:00,399 how you structure, uh, your services are really important.
Um, so I've talked a lot about that in terms of, like, are you going to bill hourly versus retainer?
Um, are you gonna backend hours into retainer?
How can you, kinda foresee scope creep if you do a retainer for access, uh, structure?

(33:17):
Um, so, you know, depending on whether you look at it from, like, a large consulting, uh, you know, kind of the big 3, right?
A lot of those folks, including boutique, like, medium-sized consulting firms, do day rates.
Um, they'll do day rates or weekly, and then, you know, monthly, backend, and t- hours is also a very popular method.

(33:40):
Um, so there's just many different ways that you can go about it.
Um, but definitely my preferred method is a scope of work with monthly retainer.
Okay.
Yeah.
So that was
I, I was about to ask that question.
So what's your, your favorite method?
.00000000023283So- Yeah, retainer for access- I, I, I tend to agree.
with a scope of work, and then I typically put in front of, uh, my partners a timeline associated with the SOW as well.

(34:07):
.0000000002328So we're doing weekly check-ins- Yeah. 336 00:34:08,820.0000000002328 --> 00:34:13,616 and, and making sure that we're hitting the deliverables that the scope set out to do in the beginning. 337 00:34:15,519.0000000002328 --> 00:34:15,820.0000000002328 Let me 338 00:34:15,820.0000000002328 --> 00:34:17,99.00000000023283 Uh, 100% agree. 339 00:34:17,99.00000000023283 --> 00:34:25,458.99999999976717 That's, uh, that's my favorite wor- way to, to work as well, and on top of that sometimes, like, um, daily workshops. 340 00:34:25,458.99999999976717 --> 00:34:33,458.99999999976717 So for, for some customers it's sometimes easier to start off with one-off engagements, but I don't like to do just, like, hourly consultations. 341 00:34:33,458.99999999976717 --> 00:34:52,199 So I, I found, at least for me, that, um, doing, like, full day workshops, you know, like 6, 8 hours, um, coming in and, like, really building something together is a very, like, uh, a solid way for a lot of, um, a lot of prospects to kinda

(34:52):
for us to gauge each other and how it's like working with each other and if it's a right fit going into a more long-term engagement.
Yeah.
I will also plug, um, weekly Looms.
Um, and this was something that I picked up with Domestique, uh, which I think is a great way to relay information back to your partners just to make sure that you're, you're on the same page, um, in sending, like

(35:18):
you know, screen share, Loom with your face, like, kind of in the bottom right or left in terms of, like, building that personal brand with your partners as well, um, and just walking them through what you had accomplished that week.
Um, so I think that's a really great method in terms of- I love it.
yeah.
Just relaying information that, like, might not be able to be relayed in a spreadsheet or an SOW or a project management tool.

(35:42):
Right?
.99999999953434So, like, you know, I think it adds a personal touch as well in terms of if you're able to 352 00:35:49,38.99999999953434 --> 00:35:54,839 or you feel comfortable with going on camera and, and adding your face, like, kind of in the bottom left or right.
Um, but you can also do it without that functionality turned on.
You can just record it in screen share.
Um, and I think that that's a really great way to level set on the weekly, um, accomplishments or, uh, deliverables that you were able to do.I, um, I like that idea.

(36:12):
Uh, I'm gonna, I'm gonna start doing that as well, so thank you.
Yeah.
G- gotta give that one to Domestique as well.
Credit is due when it, where it's due.
Right.
Um, so, uh, last quick-fire question.
Um, where do you see the future of fractional work?
love this question.

(36:32):
Um, so ballpark in the United States, 10% of the entire labor force is self-employed, um, and it hit a high during the pandemic, during COVID.
.0000000004657Um, I think it was, like, closer to 11 or 12%.
Um, personally, and I've been wrong plenty of times before, so-

(36:53):
with a prediction, I'll definitely caveat that I could totally be wrong.
Um, but I, I only see the fractional, uh, market and labor force getting larger and larger.
Um, kind of what validates that as well, are systems and tools that are built for that market specifically.

(37:13):
Um, so, you know, one that I use currently, uh, is collective.com.
Uh, they're a bookkeeping, tax, uh, and invoice system.
Um, and they are specifically built for, uh, solopreneurs.
Um, they reclassify you as a S corp if your revenue, uh, is high enough and it makes sense in order to actually have that S corp filing.

(37:42):
Um, and then another, you know, company in that kind of competitor set that I think validates this space a lot is that, like, not only is it just self-employment is, you know, about a tenth of the market, but there are large B2B SaaS offerings, both from a managed service and a self-service perspective that are being built to service this market as well.

(38:07):
Um, so- Yeah.
Formations is another one, also kind of in the same realm as bookkeeping, taxes, et cetera.
Um, and then I will also call out Found, uh, which is a self-service tool, um, rather than the 2 Okay.
that I just kind of listed out, which are more managed service.
Um, so, uh, and I think Found is also geared towards small businesses overall, uh, rather than, like, kind of just a solopreneur aspect.

(38:34):
Um, but I think that on top of the fact that there are a lot of layoffs and firings, people are gonna find themselves in this transition area of their career where they debate, "Do I go fractional for the first time?"
Because their hand is forced in some way, right?
Um- Yeah.
the way that I kind of phrase it is, uh, "Made a hard decision easy," right?

(38:58):
So if you're laid off- Yeah.
for the first time and you've been thinkin' in your own head, "I think I can do this.
I think I can build out my own freelance shop," uh, then take a crack at it, um, while you're searching- Yeah.
.00000000046566for your next full-time gig, right? 388 00:39:14,229.00000000046566 --> 00:39:14,669 Um- Yeah.
you can do both where you can try to take on a project or two and see whether you like it or not in a very similar manner if you were full time and trying to do it on the side.

(39:24):
.99999999953434So if you're in your full-time job search, try to pick up a, a project or 2 based on your personal relationships. 391 00:39:32,328.99999999953434 --> 00:39:33,288.99999999953434 Um- Exactly. 392 00:39:33,288.99999999953434 --> 00:39:41,278.00000000046566 so, you know, I think that the, the fractional, uh, market is only gonna get bigger over the next 5 years.
I, uh, I tend to agree.

(39:45):
.9999999995343I think that, um, I'm seeing more and more varied fractionals, um, as well in, in various positions and, and various, uh, um, capacities and, and, and roles and, um, specializations in terms of industries that they work with or things like that, so, um, yeah.

(40:08):
Um, okay, so our final question and then, uh, we'll, uh, uh, start wrapping things up.
Um, if you could give one piece of advice, um, to someone who's, now thinking about going fractional for the first time.
And, you know, we've talked a lot about this already in the episode.
Um, you gave already a couple of great pieces of advice, so one last piece of advice.

(40:34):
Set up a CRM immediately.
I, uh, I am not surprised.
Um- I mean, I, I just, I can't stress it enough.
Uh, a lot of people wait on it.
You're not a computer.
I mean, you're never gonna remember the email that you sent to, uh, Joe or Sophia, uh, from, you know, 6 months ago.

(40:55):
Uh, and, like, those contacts and companies really do matter if you are gonna stick around in this game for, for even 12 months, right?
So, I mean, my, my biggest piece of advice is get a CRM, which is the easiest thing to do.
You literally can get a free tool, almost anywhere.

(41:15):
I think I listed about half dozen more- Yeah.
on this, on this chat today.
Yes.
And then my second, you know, go-to piece of advice, which is directly related to the workshop, is build out an ICP.
Like, just do it from the get so that you know exactly the type of, uh, project and, uh, partner that you're trying to onboard.

(41:41):
And that's a very, very important piece of advice.
Um, all right.
So, I think we'll, uh, we'll wrap this up.
Um, thank you, Jack, for, you know, for being with, uh, with, uh, with me today, um, you know, sharing, uh, some, some insights and some interesting stories and recommendations.

(42:03):
.0000000004657Um, you know, if anyone who's listening wants to follow up or, you know, get that, uh, um, get that resource, or be in touch, what's the best way to, uh, to find you? 418 00:42:13,538.9999999995343 --> 00:42:13,999 Yeah.
Uh, LinkedIn.
.99999999953434Um, so, of course my name will be spelled out, but it's Jack Oliphant. 421 00:42:19,38.99999999953434 --> 00:42:22,619 Um, so give me a follow on LinkedIn, shoot me a DM.
Um, all over the internet, uh, so it's pretty easy to find me.

(42:26):
But LinkedIn is, is the number one, and then number 2 would be my website, so just fill out the contact form.
Uh, so it's oliphantstrategies.com.
O-L-I- It will, uh-
P-H-A-N-T-
it will be in the show notes-
T.
of course.
Awesome.
Well, you know, you got it.
Um, so I definitely would recommend, uh, just filling out the contact form.
Believe it or not, it's, uh, built in Webflow by myself- Yes.

(42:49):
.00000000046566and then, uh, integrated with HubSpot.
Not surprising.
Um, awesome.
So, um, again, thank you, uh, for, for, uh, for being here today, and thank you, uh, for listening.
Um, and if you loved this conversation, subscribe, uh, like, share, leave a review, um, do the things that you do when you like a podcast.

(43:17):
Um, thank you again, um, for- Yeah.
No, thank you for having me on.
being today.
I really appreciate the time today.
And thank you everybody who made it to the end here as well.
Um, I'm always up for a chat, so if, if you wanna reach out again, um, or anybody who's listening wants to reach out, please just give me a shout.

(43:37):
All right.
Thank you.
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