June 11, 2025 • 33 mins
FREE TRAINING: https://start.shahiddurrani.com/
Shahid Durrani sits down with Randy Wootton on the Super Entrepreneurs Podcast for a conversation that's packed with real insights. Randy's spent years turning around SaaS companies and building teams that actually work well together, and he credits a lot of that success to lessons he learned in the military.
In this episode, Randy breaks down his approach to fearless leadership and talks about the four key support systems he relies on when business gets tough. He also walks through his go-to 90-day game plan for making real changes happen fast.
You'll hear Randy's take on making decisions when the pressure's on, why having good mentors and coaches matters so much, and how building genuine relationships is what really drives business growth. If you're an entrepreneur or leader looking to step up your game and build something that lasts, this conversation is definitely worth your time.
Chapter Stamps:
03:07 Randy's Military Background and Leadership Lessons
08:58 The Importance of Mentorship and Coaching
10:03 Building Effective Peer and Advisory Groups
11:49 Facing Fear and Embracing Change
12:16 The Value of Mentorship and Giving Back
14:25 The Importance of Authentic Relationships
15:50 Finding the Right Mentor or Coach
18:29 Comparing Nutritionists: Different Approaches
19:33 First 90 Days Strategy
20:48 The Four L's Approach
23:06 Quick Wins and Roadmap
25:38 Building Relationships and Trust
26:06 Personality Tests and Team Dynamics
29:26 Meditation and Mindfulness
30:22 The Power of Presence
Pullout Quotes:
“Lead, follow, or get out of the way.”
“In the corporate sector, there’s a lot of fear of failure, but in the military, you learn to step up and say, ‘I got it.’”
“You need a mentor, a coach, a peer group, and a personal advisory board—those four groups will change your life.”
“Software is a people business. If you’re not interested in authentic relationships, people will see that you’re just solving for power or money.”
“My greatest sense of accomplishment is when people I’ve worked with reach out years later and say, ‘You made an impact.’”
Social:
Website: https://ceox.io https://www.maxio.com/authors/randy-wootton
LinkedIn: https://www.linkedin.com/in/randy-wootton-910/
Instagram: https://www.instagram.com/wearemaxio/
Disclaimer:
Please be aware that the opinions and perspectives conveyed in this podcast are solely those of our guests and do not necessarily represent the views, ideologies, or principles of Super Entrepreneurs Podcast, its associated entities, or any organizations they represent or are affiliated with. We provide a platform for discussion and exploration, and the content of each episode is understood to be independent expressions from our guests, rather than a reflection of the beliefs held by the podcast or its hosts.
Notice to the Super Entrepreneurs community:
Before we part, remember to join our Private Facebook group, 'Mindset for Business Success'! Here we share mindset wisdom to elevate your life and business LIVE every Tuesday morning (EST). Ready for a transformative journey? This group is your key to unlocking potential and achieving business growth.
Don’t miss out on this i
Mark as Played
Transcript
Episode Transcript
Available transcripts are automatically generated. Complete accuracy is not guaranteed.
(00:00):
The fourth group I thinkis critically important.
(00:03):
It's having a personal advisoryboard, and these are people who've
known you for 20 years, who knewyou when you were young, right?
And know who you really are,and they only care about you.
Their vested interest is your success.
And I use that group whenI'm making life changes.
(00:36):
Welcome back to SuperEntrepreneurs Podcast.
I'm your host, Shahid Durrani.
This is the show where we dive into theminds of high performing entrepreneurs,
innovators, and world class leaders.
If you're someone who's always lookingto grow, push limits, think and do.
(00:57):
Bigger.
You're in the right place Todaywe have with us Randy Wooten.
Randy is the CEO of Maxio, a companyhelping high growth SaaS businesses get
their billing metrics and financial ops inorder so they can scale with confidence.
He's also held majorleadership roles at Salesforce.
(01:21):
Microsoft served as a CEO ofRocket Fuel percolate, let's
welcome Randy to our show.
Thank you, Randy.
Thanks for having me.
Delighted to be here andexcited for the conversation.
Yeah, no problem.
So you're not a CEO ofMaxo anymore, correct?
So we just did a transition.
I'd been there for about three years.
(01:41):
Helping Maxio was the mashup of twocompanies, SaaS optics in charge,
Gify who'd been around for a while,primarily focused on the B2B SaaS
space and doing, as you mentionedhelping to support billing, invoicing.
And RevRack and reporting.
And so my remit over the last threeyears has been to integrate those
two companies, bring 'em together,create Maxo as a brand, as an
(02:03):
experience, and broaden its platform.
And now I've handed off Baton to anotherCEO who's gonna continue that and.
Continue moving forward.
So yeah, so it was athree year tour of duty.
It's what I do The lastI've been a CEO three times.
I'm one of those people that's likea professional CEO that comes in and
helps either do a strategy pivot ora transformation, or in this case,
(02:26):
drive the integration of two companies.
So it was a great learningexperience, had a lot of fun and
excited for Max's continued success.
That's great.
So before we get into this,I have a question for the
audience especially on YouTube.
Okay.
If you can share one lesson you havelearned from a leader I. Who truly
(02:48):
inspired you, I would love to hear that.
Please drop it in the commentsand I'm sure Randy would as well.
And anyone else that's watchingwould love to hear from you as well.
So thank you so much.
Back to finding out about this, I.This journey of yours, Randy and how
we can amplify someone's life today.
You've been in the Navy, right?
(03:09):
Then you actually wentinto Silicon Valley.
How do you think, being trained in thosekind of positions helped you make proper
decision making skills in business.
Yeah I think the military wasa great training environment.
(03:29):
And I think what I tell people is inthe military one of the old adages
is, lead follower get out of the way.
And what that means is you're often,when you start in the military,
you're you're learning how to be afollower and it's not a blind follower.
Like you're not gonna do things thatare illegal, but you are gonna learn
how to take orders and execute.
And your ability to respond quickly andget things done is critically important.
(03:52):
And then you become a leader andthen you've learned, you have empathy
with what it means to be a follower,and then you become a leader.
And then you are trying to be smartabout the decisions you're making, but
you expect when the when a decision isbeing made that people will go execute.
And so I think there's thisjust real clarity there.
And what we don't have time for in themilitary, there's a lot of in, wartime is.
A lot of debate and so you want to dothe hard work ahead of time, do the
(04:15):
plans like you, there's very thoughtfulplanning exercise, but then when you're
flying over the, I was an aviatorBombardier navigator in a six intruders.
When you're flying over thecountry, you have to be racking,
re reacting to what's unfolding.
I think the other thing in the military,they put an enormous premium on training.
So when I graduated the Naval Academy,it took me three years to get through
flight school to get through thetraining with the out landings.
(04:41):
This commitment to developing skillsover time and learning how to do the job
so that when you're faced in those lifeand death situations, like you can make
the instantaneous decision, but it's notjust a gut move, it's a move that has
been trained and refined based on all theexperience you've had up to that point.
And so I think as you extrapolate intothe corporate sector, I would say the
(05:02):
biggest lesson learned for me was itwas lead follow, or let's talk about it.
And I remember being at Microsoft.
And I was like why are we wastingall this time talking about it?
Is it your decision?
Is it my decision?
I don't care like you make the decision.
But I do think that in, in corporatesector writ large, one of the things
people feel like, oh, it's all consensusbased and everyone needs to agree.
And I disagree with that.
(05:23):
I think that what you want toget clear on is what is the
decision we're trying to make.
Who ultimately is gonna be responsiblefor the decision and how are
we going to make this decision?
Is it gonna be input, like we'regonna sit around and have a good
productive conversation for an hour?
We're gonna share data, we're gonna shareassumptions, and then at the end of the
day, we're going to hand it off to someoneto then make a decision and go execute.
(05:44):
What I find is that in many companiesis you'll be in a meeting and
you'll think a decision is made.
And then you come outside of the meetingand the, people are having the meeting
outside of the meeting and you're like no.
Let's be efficient.
It's done.
So I think that's the being clearabout the decision rights, right?
Who has the D?
Who's gonna make the, and I alsothink there's this sense in.
(06:04):
In the corporate sector, I've met a lot ofpeople who are willing to, who are, feel
like they have the veto and will say no.
But when you ask 'em to stepup and take it, they won't.
Because they're also afraidof being accountable.
And I think in the military, that's one ofthe things you really learn is like you're
gonna fail, but you, because you have thispractice again and again of what we need
(06:25):
is people to step up and say, I got it.
I'm gonna make it happenthe best of my ability.
And if it doesn't work right, I'm gonnacome back and we're gonna debrief and
we're gonna go off and do it again.
Yeah.
And I think in the corporate sector,there's a lot of fear of failure.
And maybe my career is not gonna advanceif I take on this big assignment.
And but they'll sit on the sidelinesand tell you all the reasons
why something isn't gonna work.
So I think that, yeah, you need this levelof people engaged in the mission, right?
(06:49):
People committed to the mission, peoplewilling to step up and then bring
real clarity about decision making.
Ever have one of those days whereyou're checking all the boxes, but still
feel like you're missing something?
I should think I justneeded to work harder.
It turns out it was my old story aboutmyself that was keeping me stuck.
(07:15):
I put together a free training on howto actually shift that internal stuff
so you can show up differently if thishits link is below in the description.
Yeah, fear, not just in thatenvironment, but fear in general
even in business is a big aspectto what an individual can achieve.
(07:40):
I remember being afraid of whatother people thought of me or,
what my family thought of me.
I was just trying to be.
Somebody that others wanted, yeah.
And there was always that fear.
I wouldn't take that step.
There's so many things I'm doingnow, that previous version of me
would be shocked, utterly that I'mdoing it, but we shift and we change.
(08:03):
And the real game changer for anindividual is when we start getting out
of our comfort zone and facing the fear.
Fear's gonna be there.
Just build a relationship with the fear.
And that's what I feel makes thatphenomenal leader you mentioned about
how you wanna be a good follower tobecome a great leader is that empathy,
(08:23):
Just understanding things asa follower that gives you the
skills to perform as a leader.
Yeah, I think that's right.
I think there's that expression of fear,the f feel the fear and do it anyways.
Yeah.
I think being a CEO or being me, beinga founder I've never been that early
stage entrepreneur only by myself.
I've always come into a situationa yeah, a company that is backed by
(08:46):
V-C-P-E-O-C-E-O of a public company.
My first actual gig of CEOwas a public company, CEO gig.
And what I would describe it as is fear.
It was also imposter syndrome.
Yes, I'm not the guy for this job.
And so I tell people, the peoplethat I coach, that there's
four things you want to have.
One, you wanna have a mentor.
So a mentor is someone who hasbeen in your specific role at
(09:08):
stage and at the right context.
So when I was public company,CEO, doing a turnaround, we
hired a guy named Tony Zali.
He'd done several public companygigs, he'd done several turns
around, and so he had very specific.
Contextually relevantexperience for me to learn from.
Number two is you wanna hire a coach.
A coach is, in my opinion,is different than a mentor.
(09:29):
A coach helps you, with yourinterpersonal effectiveness.
So when I stepped into thatrole as public company, CEO.
I had a board of directors who werevery seasoned executives and I felt
like I was, playing minor league ball,walking into the New York Yankees
and like I didn't know what to do.
And so the coach really helped me developmy skills as a leader of a boardroom
(09:49):
with very senior executives in how to.
How to work with them, how tocreate alignment, how do you get
all these different parties aligned?
Interpersonal effectiveness with theboard, with your leadership team, with how
you're showing up with your organization.
Number three, I think it's reallyvaluable to have a peer group.
And so there are several organizationsout there for early stage founders.
(10:10):
There's one called eo, I thinkit's Entrepreneurs Organization.
There's one called YPO, youngPresidents Organization.
I have been part of a group calledVistage, which is for people
that are a little bit furtheralong in the business cycle.
There are other ones out Venise,but you can find a group of.
Founders, entrepreneurs, and it's acohort and you get together on a monthly
(10:33):
or quarterly basis and you just cometogether in kovic a little bit and talk
about problems and you get feedback on it.
So you have that third group of peers,you got a mentor, a coach, peer group.
The fourth group I thinkis critically important.
It's having a personal advisoryboard, and these are people who've
known you for 20 years, who knewyou when you were young, right?
And know who you really are,and they only care about you.
(10:56):
Their vested interest is your success.
And I use that group whenI'm making life changes.
So when I've changed jobs I callthese people and we get together.
We used to get together duringcovid, like once a month.
Now it's periodically, but we always gettogether once a year for a ski trip and,
it's just you feel the love of thesepeople and the support no matter what.
(11:16):
And so now I'm facing this nexttransition and I'm trying to
figure out am I gonna retire?
Am I gonna go dig in onanother entrepreneurial effort?
Am I gonna go be an operating partner?
Am I gonna be a CEO coach?
Like having an opportunity totalk with my peer advisory group.
Really, and we're juststarting this right?
But they're gonna help me.
Parse out like the themes of my lifeand the things that I, where I've had
(11:40):
resonance and areas where I've haddissonance and I think they're gonna be
very good counselors for me as I thinkabout what it is in this next chapter.
So I think the fear part thatyou mentioned is, and large
often because you feel alone.
And so
how do you create connections?
Deliberate and intentional with peoplewho are going to, and everyone I've
(12:03):
ever asked has always welcomed it.
Sometimes you have to pay for 'em, yougotta pay for the mentor or the coach
or the but in general, like peopleare willing to meet you if you're
willing to open up and be vulnerable.
Yeah.
Investing in mentors has changed my life.
So I am in hundredpercent agreement on that.
And, the guests on the show,you'll notice they naturally
(12:27):
wanting to share what they know.
They create a program or they dosomething to align it with a mentorship
or coaching for others because they just.
Naturally want to give back.
I feel like there's this aspect ofa human being that we just want to
serve other human beings really badly.
(12:51):
I agree.
I don't know if every humanbeing is oriented in that way.
We can just look at our currentsituation of broader political
environment in terms of, yeah.
But I do think I think a lot ofpeople in the military come from
an orientation of wanting to serve.
You're starting wanting, youwanna serve your country.
I think, so that's just in my innateself is to give and, in a productive way.
(13:11):
I think the other thing is I'm verygrateful for those that invested in me.
And so my career, I would not be whereI am today without the mentors agreed.
That have impacted the career shifts.
And so I feel not paying itforward, but almost paying it back.
Yeah.
I personally part of my career at theNavy, I went back, I took a master's
in the great books and I went andtaught literature for three years.
And so I have continued on in,in seminars and other ways.
(13:36):
So I guess there are two elements to that.
One is I'm a lifelong learner.
So I think people that have thatorientation that are humble enough to
realize they don't really know it alland are just seekers of truth, are
gonna be doing that through reading.
They're gonna be taking courses,they're gonna be meeting with people.
And I think that orientation isalso I also want to be sharing ideas
(13:56):
and working with people and it's mygreatest sense of accomplishment.
Proud is when I look back over thecareer I've had 25 years in the
corporate sector and people that wereworking for me and my organizations have
now continued on in their career andthey'll reach out and say, Hey Randy,
you made an impact me on this way.
Or, I remember this.
I love this.
I don't even remember it.
(14:16):
Yeah.
But when you've been able towhat other legacy would you want?
It's not about money, it's priceless.
It's the people you've impacted,it's the relationships you've built.
Yeah.
And I tell people, softwareis a people business.
It's people that are building code.
It's people that are selling the code.
It's people that are takingcare of the customers.
That's a relationship business.
Yeah.
And so if you're not interestedin authentic relationships, people
(14:37):
are gonna suss that out and they'regonna see that you're solving for
power, you're solving for dollars.
But, we're in a world where we'reinterconnected as a species.
Yes.
And our, we are, hopefullythere'll be peace.
Yeah.
And that we will work broadlyto build more connections.
But I do think that comes from aan orientation to want to serve.
(14:57):
Yeah, if you go deep enough in therabbit hole, you'll see that everything
is one fundamentally speaking.
So I definitely agree with that.
It's great to have you doing whatyou're doing right now because people
that are actually serious, peoplethat actually say, you know what?
I need help.
That's who you're serving, really.
(15:19):
But we all need it.
We all need that helping hand.
And I feel like the people thatconnect with individuals as a mentor
or a coach, there's this intuitiveconnection that happens for them to
invest in someone when it comes to that.
They just feel that thisindividual can help me.
(15:39):
In a way that is right for me,because let's face it, nowadays,
it is really noisy online.
Almost everyone is a mentor or coach,
yeah.
Yeah.
So I think that goes back to that pointof be clear about what you're looking for.
Are you looking for help?
For example, you're an earlystage company, less than a
million bucks, and you're tryingto raise your first seed round.
(16:00):
I'm probably not the right guy foryou 'cause I've never read raise seed
capital, but there are people out therewho have and who can provide that.
So I think you want to be.
It's like picking yourinstructor in college.
Yeah.
The course that you take is primarilygonna the impact it's gonna have
on you is primarily dictated, Ithink by the professor and the
instructor more so than even the text.
(16:22):
Like I think there are people whocan get through a text on their own,
but really it's the professor or thetutor that helps unlock the mysteries
of whatever text you're looking at.
And so I think findingpeople with the appropriate.
Experiences and background forwhat you're trying to solve.
And that's why I break thosethings into three different groups.
Like the coach.
Yeah.
The person who was helping mebetter understand who I was as a
(16:46):
person and how better to interactwith these other board members.
Wasn't the person I was talking toabout how to do OPEX optimization.
And the people that I am talking to inthe advisory group, the peer group, they
may not have SaaS specific experienceand we are in that 50 to a hundred
million dollars zone in terms of revenue.
(17:07):
But they may have experience relevantexperience in terms of hiring
your next head of engineering.
And so it's where do you, what are thewho do you go to for what questions?
And what's the realm of expertise?
But even in that, in those brackets ofskills that you're looking for within that
category, there will be multiple people.
(17:30):
Yeah.
They'll have, it's just howyou feel with individuals.
Yeah.
What I'm trying to say is thatmeeting with these people to talk
to them about your situation.
And, feeling them out ina way is very important.
Just like when you bring ona staff member, you want to
interview a whole bunch of peoplebefore you make a decision.
Same way.
I feel like when you need the help,when you go and meet with these
(17:53):
different coaches and mentors and seewhere you intuitively feel, 'cause
every time I made a decision basedon that it was successful when I base
it on other more cosmetic reasons.
It wasn't great, but for me,having those options, interviewing,
seeing where you connectenergetically is super important, I
(18:15):
think.
Yeah.
No, I look MINDBODY spirit, right?
Like the person could be wicked smart,but if you don't have a connection
at heart level, or energetic level.
Yeah.
It probably won't work.
It's a good what
you're doing.
Yeah.
And what this, I'll you twoexamples, what you're doing is
great.
Yeah.
On podcasts, right?
Yeah.
Yeah.
So I've got two examples.
(18:35):
I've, I, you, so I've gotteninto nutrition, and I'm trying to
figure out how to better adjustmy macronutrients in which Yeah.
Supplements I should be taking.
And I had this experience withtwo different nutritionists.
One who was a hard ass,and I'd log my stuff.
It was a woman and she would justbeat me up about, why I wasn't
doing everything I should be doing.
Yeah.
And it was really tough.
And I felt like I was back at footballcamp and getting beaten up on, and then
(18:58):
I had this other nutrition nutritionistwho just had a different approach to it.
And the energy to your point wasmore around, Hey, this is a journey.
Yeah.
You're gonna get some of this stuff let'scelebrate the things that you're doing.
Yeah.
And here's some things to think about.
And it just, it worked for me.
Now, first nutritionist.
Has a lot of successful clients and theyhave been very successful in their way.
(19:18):
But to your point, that modalitywasn't working for me at where
I am in my career, no, not for
you.
But now your not for your soul.
That my soul.
And
so I do think all of these mentorsis, how do you find someone yeah.
That you resonate with.
Yeah.
It's important.
Can you share what your game planusually is when you enter a company?
(19:40):
Sure.
Your, for example, your first 90 day plan.
Yep.
So I'm a huge fan of the book.
91st 90 days.
Every time I start a new gig, I read it.
And this is not just, oh,it's funny that I said
90 days.
Yeah.
Oh, it's a great book.
Yeah, and I used it before I was inthe CEO role, so I think I first read
it I don't know, back in the nineties.
And what it does is it just helps youget your head around a couple of things.
(20:02):
One is when you're interviewing for a job.
You are already like in the role, and soyou need to be ready to go in terms of
what are the set of things you're lookingat, what are the questions you're asking?
Who are the conversations you want tohave before you even start on day one?
So your first 90 daysdoesn't start on day one.
It's probably starts like 30 daysprior as you're ingesting the
(20:23):
information you're trying to do theanalysis, the strategic analysis.
And obviously preplanning don'thave all the right answers, but I
do think what you're trying to doand is you're coming into a role is.
Understand, like the forestversus the trees broadly,
where is this company based?
What are its strengths?
What are its opportunities?
What's happening in thecompetitive landscape?
What would you have to believefor this to be true, to create
(20:46):
a lot of enterprise value?
Then you're doing a bunch of conversationsin that next, call it first 90 days
after you start, I think what you'redoing is I call it the four L.
You look, you listen,you laugh, and you learn.
You look, you listen,you laugh and you learn.
And so you're looking to validatethe assumptions you've made.
You're listening to people, so you'resetting up lots of one-on-ones.
(21:06):
One-on-ones with people inthe company, one-on-ones with
customers, partners, board members.
Right, learn.
So you want to be operating from aplace of just, not that you don't have a
point of view, but you want to encouragepeople to participate and validate.
So assumptions and data, helpme understand, is there more
data I need to be looking at?
(21:27):
Help me understand your assumptions.
Let me share my assumptions.
'cause the worst thing in theworld is come into a situation and
say, I got all the right answers.
No one's gonna.
Listen to you.
So you've been hired for aspecific reason 'cause of your
background skills and experiences.
Your opportunity is to figure out howto, and I can tell you examples where
I failed in this, but as you come in,like what are your initial hypothesis?
(21:50):
So a data assumptions hypothesis.
The last part was one thing that I found,i've developed over the, I don't know,
the last 10 or 15 years is I tend to beas you can probably tell, I, I talk fast.
I think fast.
I move fast.
People can feel like I'm beingtransactional in my interactions.
Like I tell people I try to buildwork relationships through the work.
(22:13):
What I found was critical is in the first90 days is just to spend time laughing.
What I mean by that is go have acoffee, go have a lunch, make sure you
have enough time where you're doingdinners, where there isn't an agenda.
I. My, my executive team willtell you the ones that I've had.
They, I'll show up at dinner with booksand I'm handing out to people and saying,
(22:33):
Hey, let's talk about this book today.
And they're like, Randy, why don'tyou just chill out and talk about kids
and what did you do on the weekend?
Yeah.
And it's just, it's super hardfor me to do that 'cause I'm
so excited about the work.
Yeah.
But that laughing componentwhere you're being very real.
And laughter brings people together.
It's joy.
And so you're being joyful at a timewhere a lot of people are probably
(22:55):
anxious that there's a new CEOstarting and is their job secure?
What's happening with the company?
So that four L tour over thefirst 30 days is wicked important.
And you can get consumed with, a bunchof little stuff that's that seems
like it's critically important, but ifyou're not making the time to get to
know the people, to try to understandthe core issues, then as you move into
(23:17):
the next 30 days, so day, 30 to 60 nowyou gotta tee up a couple of things.
You gotta tee up some quick wins.
You gotta, in my opinion, you gottafind the things where you can make a
decision where people may have not madea decision in the past and they are
waiting to see if you're gonna do it.
And one example, I was at thecompany and they had a HR leader
(23:38):
and she was fine, nice person.
But everyone thought thatshe wasn't effective.
And I showed up and, in the first 30 daysI was like, God, I need all this help.
And it's not happening.
This person is not delivering.
And so in 30 days I said,look, this isn't gonna work.
We need to move on.
And so I had a bunch of HR professionalsin my background that I've worked
with who have been superstars.
(23:59):
If you're trying to come into acompany and lead transformation,
it is a culture change.
And you need a, you need anHR partner that can do that.
And so I, I let the person go andall the executive team was like, wow,
we didn't think you would do that.
And it's why not?
And they're like blah, blah, blah.
And I was like, look, like it seemed likeyou were telling me this wasn't working
and no one was solving this problem.
(24:19):
I will make that decision.
And I had enough data pointsover the first 30 days to say,
yeah, this isn't working for me.
If it's not working for them, if itwas working for them, then I would
probably take another 30 days andsay maybe I need to tune my radar
a little bit more here because it'sworking for these people, but I don't.
Something's dissonant for me.
So anyways, I think you makethose quick decisions, quick wins,
(24:43):
initiate some programs, do somethinggood in that day, 30 to 60, and
start to build out a a roadmap.
A roadmap for the set of changes youwanna initiate, the set of programs you
wanna put in place the types of thingsyou're thinking broadly on strategy.
And so by the end of 90 days, you'vemet the people, you've learned a
bunch, you've got some quick wins,and now you can take a breath.
(25:05):
Oh, that's excellent.
Thank you so much for outliningthat whole game plan and the
relationship is a crucial part of it.
Sometimes as professionals or when we'reinfused with what we know and how we can
help people, we get really passionate ashuman beings, and I can relate to that.
When I work with individuals for theinternal mindset transformations I get
(25:28):
really enthusiastic, about this wholeidea and what can happen in their life.
So automatically.
I just want to do, likeyou mentioned, yeah.
Bringing the books right.
Yeah.
And I lose that part butoverall I'm really good at the
relationship side of things.
Just having fun, the laughter part.
But when it comes to that, Ijust, something shifts in me.
I'm just there focused.
(25:49):
But the funny thing is I shouldhave more of that in there as well.
That relationship should continue.
The laughter shouldcontinue incorporate in it.
But to your point it's sometimes.
Automatic.
It's just automatic because ofthat level of passion you have.
Yeah.
I'll give you one lesson learnedfrom Maxo was the I don't everyone's
(26:10):
probably familiar with Myers-Briggs orIntacct or insights or discs or the,
all these personality tests you cantake, and I think there are wonderful.
To use at companies I describe 'emas a year's worth of one-on-ones.
If you take a personality test,the ones I use most mostly
is called insights profiles.
I have a specific insight profile.
You have a different insight profile.
(26:31):
Your ability to you.
Use those and now you can, oryou can load 'em up into chat
GPT and I can load your profile.
I can load my profile and say,Hey, I want to talk about subject
X. Help me better frame thisknowing our two different profiles.
So I, that's a total recommendationfor people if you really want
to get to know 'em, is use thoseinterpersonal use those person that.
(26:52):
Prior, and you would haveeverybody's team on the wheel
and you'd see how they resonated.
They were either more creative,they were more like driven, they
were more detail oriented orthey're more relationship oriented.
Those are the four buckets was my teamwas very relationship oriented and so
when me coming in as super hard driving,it felt, intimidating and transactional.
(27:13):
And so we had something called a roundof good at the beginning of our executive
team meetings for the first 15 minutes.
It was not about business.
It was about, Hey what happened in yourlife over the weekend and what do you want
what good thing happened in your life?
And I'm sitting here like fighting Mike.
Fingers because all I want to do isget into the business and instead we're
(27:33):
talking about kids and dogs and vacations.
I could see that, oh my God.
However, having said that, being in ahybrid work environment, giving a little
opportunity for us to laugh to, to builda relationship, a built stronger bonds.
And trust with that team so that thenwhen we started to get into the harder
(27:54):
conversations around the business,we are operating from a place of
where we've already leaning in to therelationship versus showing up and
being on the defense or the offenseas you're taking, sales guys can play
marketing, playing about sales, likeyou de power the intensity and instead.
(28:15):
Empower the relationship.
Randy, that's great, I know whatyou're talking about that level
of go go, but you still have thisunderlying calmness about you.
There's this.
This feeling of, yeah, it'sgonna be fine, kind of thing.
That's what I'm getting from you.
Is that a kind of feedbackyou get from people?
(28:35):
Yeah, I think so.
I think the feedback I get, it isusually along a couple dimensions.
But one thing I would say is havingbeen in the military, what I tell people
is look, no one's in corporate sector.
No one's dying here.
This isn't like in death decisions.
So like it's all just ratcheted,this just relax, just relax.
Number two, I've been working onmyself for 20 something years and
I was a whole lot more intense.
(28:56):
Good.
When I was younger.
Yeah, I would make acouple recommendations.
There's just broadly therapy.
Yeah, there's a great organization outthere called pathwise leadership.org.
Pathwise leadership.org.
And I've been in that programfor, I don't know, 12 or 15
years I've helped lead cohorts.
It's incredibly powerfuland it roots in great.
(29:16):
How do you be present and how doyou interact with other people?
It's tied in beautiful with psychology.
And so it's just, it's super cool.
Great.
So that allows you to have some space.
Perfect.
But I would say in meditation, havingmeditation helps settle everything down.
I do.
You
meditate?
I do.
I wax and wane with it.
(29:37):
Yeah, things are super intense and I'm notgetting a lot of sleep and I'm traveling.
My meditation turns into a nap.
But like this morning I gotup and meditated and I'm just,
I think it that was great.
Helps you be present, beconscious about your body.
Yes.
It helps you create a space,I think if whatever meditation
you're doing, but like gratefulnessfor what you have in your life.
(29:59):
And again, I think you're settingthe conditions for the day if
you're brilliant, deliberate,and intentional about it.
It can really I think it canplay forward throughout the day.
Yeah.
And now you can get, tossed and turned andbeat up by different things and surprises.
And if you can bring yourselfback to, being present.
And thus makes all.
(30:21):
Yeah.
And in a way, what meditation does, ittrains the mind to be a specific way,
for example, you mentioned being present.
Yeah.
And that comes from the calmness, right?
Yeah.
And I practice meditation alot, I worked on creating the
meditative state habitually.
So meaning in each moment, thenI started allowing content to
(30:45):
come in that present moment.
So working on things, actiontaking from that place Yeah.
Of presence.
And then I started getting better atthat, then I started incorporating it
more and more into day-to-day life,
yep.
And then slowly it starts becoming you.
You start becoming thatspaciousness or that stillness.
Yeah, and it's a game changer becausenow life is not this troubled thing
(31:09):
oh my God, what am I gonna do?
It becomes a joyful thing.
Now you're in a flow state where, yeah,good and bad is coming, but you understand
more because you're more expanded.
You.
Awareness, the consciousness more expandedwhere you are allowing things to unfold
rather than why did this happen to me?
Yeah.
So I really appreciate meetingyou, it was great talking to you.
(31:32):
Definitely keep in touch.
Sure.
If there's anything happeningin the future, let us know.
Yeah sure.
If people are interested in learningmore, so I've written, I'm working
on a book, it's called The EightSecrets of Success for SaaS CEOs.
So it's primarily focusedon software as a service.
You can find a lot ofthe chapters on LinkedIn.
And then I literally just launcheda CEO advisory service called CEOX.
(31:56):
Io and so I'm working with a coupleof companies right now, but if people
are interested in more of this andtrying to figure out if they need a
CEO coach and if I'm the right guy, andto your point with the right energy,
yeah.
Come check me out, Randy CEO
x.io.
Awesome.
Love it.
Thank you so much, Randy, and yeah, that'sa great thing about podcasts because
(32:19):
you get the audio side of the energyand the video as well, and depending
on the kind of show you go on, but mostof them now are both video and audio.
Yeah.
Yep.
Is just being you, you just beingyou and talking and that there is,
there's people searching for help.
Yeah.
And there's so many options, so manynews by you making the decision, going
(32:39):
on podcasts is one of the most importantthings you can do to elevate your career
and your network and everything else thatcomes with it, especially relationships.
That's why I love this, right?
Because I get to meet people and build.
Yeah, totally.
That's what I loved about my
podcast.
It was just the conversation you'rehaving, the people you're meeting,
finding out about their lives.
So thank you for the opportunityto be here and you my pleasure.
(33:02):
Wish you the best
The fourth group I thinkis critically important.
(00:03):
It's having a personal advisoryboard, and these are people who've
known you for 20 years, who knewyou when you were young, right?
And know who you really are,and they only care about you.
Their vested interest is your success.
And I use that group whenI'm making life changes.
(00:36):
Welcome back to SuperEntrepreneurs Podcast.
I'm your host, Shahid Durrani.
This is the show where we dive into theminds of high performing entrepreneurs,
innovators, and world class leaders.
If you're someone who's always lookingto grow, push limits, think and do.
(00:57):
Bigger.
You're in the right place Todaywe have with us Randy Wooten.
Randy is the CEO of Maxio, a companyhelping high growth SaaS businesses get
their billing metrics and financial ops inorder so they can scale with confidence.
He's also held majorleadership roles at Salesforce.
(01:21):
Microsoft served as a CEO ofRocket Fuel percolate, let's
welcome Randy to our show.
Thank you, Randy.
Thanks for having me.
Delighted to be here andexcited for the conversation.
Yeah, no problem.
So you're not a CEO ofMaxo anymore, correct?
So we just did a transition.
I'd been there for about three years.
(01:41):
Helping Maxio was the mashup of twocompanies, SaaS optics in charge,
Gify who'd been around for a while,primarily focused on the B2B SaaS
space and doing, as you mentionedhelping to support billing, invoicing.
And RevRack and reporting.
And so my remit over the last threeyears has been to integrate those
two companies, bring 'em together,create Maxo as a brand, as an
(02:03):
experience, and broaden its platform.
And now I've handed off Baton to anotherCEO who's gonna continue that and.
Continue moving forward.
So yeah, so it was athree year tour of duty.
It's what I do The lastI've been a CEO three times.
I'm one of those people that's likea professional CEO that comes in and
helps either do a strategy pivot ora transformation, or in this case,
(02:26):
drive the integration of two companies.
So it was a great learningexperience, had a lot of fun and
excited for Max's continued success.
That's great.
So before we get into this,I have a question for the
audience especially on YouTube.
Okay.
If you can share one lesson you havelearned from a leader I. Who truly
(02:48):
inspired you, I would love to hear that.
Please drop it in the commentsand I'm sure Randy would as well.
And anyone else that's watchingwould love to hear from you as well.
So thank you so much.
Back to finding out about this, I.This journey of yours, Randy and how
we can amplify someone's life today.
You've been in the Navy, right?
(03:09):
Then you actually wentinto Silicon Valley.
How do you think, being trained in thosekind of positions helped you make proper
decision making skills in business.
Yeah I think the military wasa great training environment.
(03:29):
And I think what I tell people is inthe military one of the old adages
is, lead follower get out of the way.
And what that means is you're often,when you start in the military,
you're you're learning how to be afollower and it's not a blind follower.
Like you're not gonna do things thatare illegal, but you are gonna learn
how to take orders and execute.
And your ability to respond quickly andget things done is critically important.
(03:52):
And then you become a leader andthen you've learned, you have empathy
with what it means to be a follower,and then you become a leader.
And then you are trying to be smartabout the decisions you're making, but
you expect when the when a decision isbeing made that people will go execute.
And so I think there's thisjust real clarity there.
And what we don't have time for in themilitary, there's a lot of in, wartime is.
A lot of debate and so you want to dothe hard work ahead of time, do the
(04:15):
plans like you, there's very thoughtfulplanning exercise, but then when you're
flying over the, I was an aviatorBombardier navigator in a six intruders.
When you're flying over thecountry, you have to be racking,
re reacting to what's unfolding.
I think the other thing in the military,they put an enormous premium on training.
So when I graduated the Naval Academy,it took me three years to get through
flight school to get through thetraining with the out landings.
(04:41):
This commitment to developing skillsover time and learning how to do the job
so that when you're faced in those lifeand death situations, like you can make
the instantaneous decision, but it's notjust a gut move, it's a move that has
been trained and refined based on all theexperience you've had up to that point.
And so I think as you extrapolate intothe corporate sector, I would say the
(05:02):
biggest lesson learned for me was itwas lead follow, or let's talk about it.
And I remember being at Microsoft.
And I was like why are we wastingall this time talking about it?
Is it your decision?
Is it my decision?
I don't care like you make the decision.
But I do think that in, in corporatesector writ large, one of the things
people feel like, oh, it's all consensusbased and everyone needs to agree.
And I disagree with that.
(05:23):
I think that what you want toget clear on is what is the
decision we're trying to make.
Who ultimately is gonna be responsiblefor the decision and how are
we going to make this decision?
Is it gonna be input, like we'regonna sit around and have a good
productive conversation for an hour?
We're gonna share data, we're gonna shareassumptions, and then at the end of the
day, we're going to hand it off to someoneto then make a decision and go execute.
(05:44):
What I find is that in many companiesis you'll be in a meeting and
you'll think a decision is made.
And then you come outside of the meetingand the, people are having the meeting
outside of the meeting and you're like no.
Let's be efficient.
It's done.
So I think that's the being clearabout the decision rights, right?
Who has the D?
Who's gonna make the, and I alsothink there's this sense in.
(06:04):
In the corporate sector, I've met a lot ofpeople who are willing to, who are, feel
like they have the veto and will say no.
But when you ask 'em to stepup and take it, they won't.
Because they're also afraidof being accountable.
And I think in the military, that's one ofthe things you really learn is like you're
gonna fail, but you, because you have thispractice again and again of what we need
(06:25):
is people to step up and say, I got it.
I'm gonna make it happenthe best of my ability.
And if it doesn't work right, I'm gonnacome back and we're gonna debrief and
we're gonna go off and do it again.
Yeah.
And I think in the corporate sector,there's a lot of fear of failure.
And maybe my career is not gonna advanceif I take on this big assignment.
And but they'll sit on the sidelinesand tell you all the reasons
why something isn't gonna work.
So I think that, yeah, you need this levelof people engaged in the mission, right?
(06:49):
People committed to the mission, peoplewilling to step up and then bring
real clarity about decision making.
Ever have one of those days whereyou're checking all the boxes, but still
feel like you're missing something?
I should think I justneeded to work harder.
It turns out it was my old story aboutmyself that was keeping me stuck.
(07:15):
I put together a free training on howto actually shift that internal stuff
so you can show up differently if thishits link is below in the description.
Yeah, fear, not just in thatenvironment, but fear in general
even in business is a big aspectto what an individual can achieve.
(07:40):
I remember being afraid of whatother people thought of me or,
what my family thought of me.
I was just trying to be.
Somebody that others wanted, yeah.
And there was always that fear.
I wouldn't take that step.
There's so many things I'm doingnow, that previous version of me
would be shocked, utterly that I'mdoing it, but we shift and we change.
(08:03):
And the real game changer for anindividual is when we start getting out
of our comfort zone and facing the fear.
Fear's gonna be there.
Just build a relationship with the fear.
And that's what I feel makes thatphenomenal leader you mentioned about
how you wanna be a good follower tobecome a great leader is that empathy,
(08:23):
Just understanding things asa follower that gives you the
skills to perform as a leader.
Yeah, I think that's right.
I think there's that expression of fear,the f feel the fear and do it anyways.
Yeah.
I think being a CEO or being me, beinga founder I've never been that early
stage entrepreneur only by myself.
I've always come into a situationa yeah, a company that is backed by
(08:46):
V-C-P-E-O-C-E-O of a public company.
My first actual gig of CEOwas a public company, CEO gig.
And what I would describe it as is fear.
It was also imposter syndrome.
Yes, I'm not the guy for this job.
And so I tell people, the peoplethat I coach, that there's
four things you want to have.
One, you wanna have a mentor.
So a mentor is someone who hasbeen in your specific role at
(09:08):
stage and at the right context.
So when I was public company,CEO, doing a turnaround, we
hired a guy named Tony Zali.
He'd done several public companygigs, he'd done several turns
around, and so he had very specific.
Contextually relevantexperience for me to learn from.
Number two is you wanna hire a coach.
A coach is, in my opinion,is different than a mentor.
(09:29):
A coach helps you, with yourinterpersonal effectiveness.
So when I stepped into thatrole as public company, CEO.
I had a board of directors who werevery seasoned executives and I felt
like I was, playing minor league ball,walking into the New York Yankees
and like I didn't know what to do.
And so the coach really helped me developmy skills as a leader of a boardroom
(09:49):
with very senior executives in how to.
How to work with them, how tocreate alignment, how do you get
all these different parties aligned?
Interpersonal effectiveness with theboard, with your leadership team, with how
you're showing up with your organization.
Number three, I think it's reallyvaluable to have a peer group.
And so there are several organizationsout there for early stage founders.
(10:10):
There's one called eo, I thinkit's Entrepreneurs Organization.
There's one called YPO, youngPresidents Organization.
I have been part of a group calledVistage, which is for people
that are a little bit furtheralong in the business cycle.
There are other ones out Venise,but you can find a group of.
Founders, entrepreneurs, and it's acohort and you get together on a monthly
(10:33):
or quarterly basis and you just cometogether in kovic a little bit and talk
about problems and you get feedback on it.
So you have that third group of peers,you got a mentor, a coach, peer group.
The fourth group I thinkis critically important.
It's having a personal advisoryboard, and these are people who've
known you for 20 years, who knewyou when you were young, right?
And know who you really are,and they only care about you.
(10:56):
Their vested interest is your success.
And I use that group whenI'm making life changes.
So when I've changed jobs I callthese people and we get together.
We used to get together duringcovid, like once a month.
Now it's periodically, but we always gettogether once a year for a ski trip and,
it's just you feel the love of thesepeople and the support no matter what.
(11:16):
And so now I'm facing this nexttransition and I'm trying to
figure out am I gonna retire?
Am I gonna go dig in onanother entrepreneurial effort?
Am I gonna go be an operating partner?
Am I gonna be a CEO coach?
Like having an opportunity totalk with my peer advisory group.
Really, and we're juststarting this right?
But they're gonna help me.
Parse out like the themes of my lifeand the things that I, where I've had
(11:40):
resonance and areas where I've haddissonance and I think they're gonna be
very good counselors for me as I thinkabout what it is in this next chapter.
So I think the fear part thatyou mentioned is, and large
often because you feel alone.
And so
how do you create connections?
Deliberate and intentional with peoplewho are going to, and everyone I've
(12:03):
ever asked has always welcomed it.
Sometimes you have to pay for 'em, yougotta pay for the mentor or the coach
or the but in general, like peopleare willing to meet you if you're
willing to open up and be vulnerable.
Yeah.
Investing in mentors has changed my life.
So I am in hundredpercent agreement on that.
And, the guests on the show,you'll notice they naturally
(12:27):
wanting to share what they know.
They create a program or they dosomething to align it with a mentorship
or coaching for others because they just.
Naturally want to give back.
I feel like there's this aspect ofa human being that we just want to
serve other human beings really badly.
(12:51):
I agree.
I don't know if every humanbeing is oriented in that way.
We can just look at our currentsituation of broader political
environment in terms of, yeah.
But I do think I think a lot ofpeople in the military come from
an orientation of wanting to serve.
You're starting wanting, youwanna serve your country.
I think, so that's just in my innateself is to give and, in a productive way.
(13:11):
I think the other thing is I'm verygrateful for those that invested in me.
And so my career, I would not be whereI am today without the mentors agreed.
That have impacted the career shifts.
And so I feel not paying itforward, but almost paying it back.
Yeah.
I personally part of my career at theNavy, I went back, I took a master's
in the great books and I went andtaught literature for three years.
And so I have continued on in,in seminars and other ways.
(13:36):
So I guess there are two elements to that.
One is I'm a lifelong learner.
So I think people that have thatorientation that are humble enough to
realize they don't really know it alland are just seekers of truth, are
gonna be doing that through reading.
They're gonna be taking courses,they're gonna be meeting with people.
And I think that orientation isalso I also want to be sharing ideas
(13:56):
and working with people and it's mygreatest sense of accomplishment.
Proud is when I look back over thecareer I've had 25 years in the
corporate sector and people that wereworking for me and my organizations have
now continued on in their career andthey'll reach out and say, Hey Randy,
you made an impact me on this way.
Or, I remember this.
I love this.
I don't even remember it.
(14:16):
Yeah.
But when you've been able towhat other legacy would you want?
It's not about money, it's priceless.
It's the people you've impacted,it's the relationships you've built.
Yeah.
And I tell people, softwareis a people business.
It's people that are building code.
It's people that are selling the code.
It's people that are takingcare of the customers.
That's a relationship business.
Yeah.
And so if you're not interestedin authentic relationships, people
(14:37):
are gonna suss that out and they'regonna see that you're solving for
power, you're solving for dollars.
But, we're in a world where we'reinterconnected as a species.
Yes.
And our, we are, hopefullythere'll be peace.
Yeah.
And that we will work broadlyto build more connections.
But I do think that comes from aan orientation to want to serve.
(14:57):
Yeah, if you go deep enough in therabbit hole, you'll see that everything
is one fundamentally speaking.
So I definitely agree with that.
It's great to have you doing whatyou're doing right now because people
that are actually serious, peoplethat actually say, you know what?
I need help.
That's who you're serving, really.
(15:19):
But we all need it.
We all need that helping hand.
And I feel like the people thatconnect with individuals as a mentor
or a coach, there's this intuitiveconnection that happens for them to
invest in someone when it comes to that.
They just feel that thisindividual can help me.
(15:39):
In a way that is right for me,because let's face it, nowadays,
it is really noisy online.
Almost everyone is a mentor or coach,
yeah.
Yeah.
So I think that goes back to that pointof be clear about what you're looking for.
Are you looking for help?
For example, you're an earlystage company, less than a
million bucks, and you're tryingto raise your first seed round.
(16:00):
I'm probably not the right guy foryou 'cause I've never read raise seed
capital, but there are people out therewho have and who can provide that.
So I think you want to be.
It's like picking yourinstructor in college.
Yeah.
The course that you take is primarilygonna the impact it's gonna have
on you is primarily dictated, Ithink by the professor and the
instructor more so than even the text.
(16:22):
Like I think there are people whocan get through a text on their own,
but really it's the professor or thetutor that helps unlock the mysteries
of whatever text you're looking at.
And so I think findingpeople with the appropriate.
Experiences and background forwhat you're trying to solve.
And that's why I break thosethings into three different groups.
Like the coach.
Yeah.
The person who was helping mebetter understand who I was as a
(16:46):
person and how better to interactwith these other board members.
Wasn't the person I was talking toabout how to do OPEX optimization.
And the people that I am talking to inthe advisory group, the peer group, they
may not have SaaS specific experienceand we are in that 50 to a hundred
million dollars zone in terms of revenue.
(17:07):
But they may have experience relevantexperience in terms of hiring
your next head of engineering.
And so it's where do you, what are thewho do you go to for what questions?
And what's the realm of expertise?
But even in that, in those brackets ofskills that you're looking for within that
category, there will be multiple people.
(17:30):
Yeah.
They'll have, it's just howyou feel with individuals.
Yeah.
What I'm trying to say is thatmeeting with these people to talk
to them about your situation.
And, feeling them out ina way is very important.
Just like when you bring ona staff member, you want to
interview a whole bunch of peoplebefore you make a decision.
Same way.
I feel like when you need the help,when you go and meet with these
(17:53):
different coaches and mentors and seewhere you intuitively feel, 'cause
every time I made a decision basedon that it was successful when I base
it on other more cosmetic reasons.
It wasn't great, but for me,having those options, interviewing,
seeing where you connectenergetically is super important, I
(18:15):
think.
Yeah.
No, I look MINDBODY spirit, right?
Like the person could be wicked smart,but if you don't have a connection
at heart level, or energetic level.
Yeah.
It probably won't work.
It's a good what
you're doing.
Yeah.
And what this, I'll you twoexamples, what you're doing is
great.
Yeah.
On podcasts, right?
Yeah.
Yeah.
So I've got two examples.
(18:35):
I've, I, you, so I've gotteninto nutrition, and I'm trying to
figure out how to better adjustmy macronutrients in which Yeah.
Supplements I should be taking.
And I had this experience withtwo different nutritionists.
One who was a hard ass,and I'd log my stuff.
It was a woman and she would justbeat me up about, why I wasn't
doing everything I should be doing.
Yeah.
And it was really tough.
And I felt like I was back at footballcamp and getting beaten up on, and then
(18:58):
I had this other nutrition nutritionistwho just had a different approach to it.
And the energy to your point wasmore around, Hey, this is a journey.
Yeah.
You're gonna get some of this stuff let'scelebrate the things that you're doing.
Yeah.
And here's some things to think about.
And it just, it worked for me.
Now, first nutritionist.
Has a lot of successful clients and theyhave been very successful in their way.
(19:18):
But to your point, that modalitywasn't working for me at where
I am in my career, no, not for
you.
But now your not for your soul.
That my soul.
And
so I do think all of these mentorsis, how do you find someone yeah.
That you resonate with.
Yeah.
It's important.
Can you share what your game planusually is when you enter a company?
(19:40):
Sure.
Your, for example, your first 90 day plan.
Yep.
So I'm a huge fan of the book.
91st 90 days.
Every time I start a new gig, I read it.
And this is not just, oh,it's funny that I said
90 days.
Yeah.
Oh, it's a great book.
Yeah, and I used it before I was inthe CEO role, so I think I first read
it I don't know, back in the nineties.
And what it does is it just helps youget your head around a couple of things.
(20:02):
One is when you're interviewing for a job.
You are already like in the role, and soyou need to be ready to go in terms of
what are the set of things you're lookingat, what are the questions you're asking?
Who are the conversations you want tohave before you even start on day one?
So your first 90 daysdoesn't start on day one.
It's probably starts like 30 daysprior as you're ingesting the
(20:23):
information you're trying to do theanalysis, the strategic analysis.
And obviously preplanning don'thave all the right answers, but I
do think what you're trying to doand is you're coming into a role is.
Understand, like the forestversus the trees broadly,
where is this company based?
What are its strengths?
What are its opportunities?
What's happening in thecompetitive landscape?
What would you have to believefor this to be true, to create
(20:46):
a lot of enterprise value?
Then you're doing a bunch of conversationsin that next, call it first 90 days
after you start, I think what you'redoing is I call it the four L.
You look, you listen,you laugh, and you learn.
You look, you listen,you laugh and you learn.
And so you're looking to validatethe assumptions you've made.
You're listening to people, so you'resetting up lots of one-on-ones.
(21:06):
One-on-ones with people inthe company, one-on-ones with
customers, partners, board members.
Right, learn.
So you want to be operating from aplace of just, not that you don't have a
point of view, but you want to encouragepeople to participate and validate.
So assumptions and data, helpme understand, is there more
data I need to be looking at?
(21:27):
Help me understand your assumptions.
Let me share my assumptions.
'cause the worst thing in theworld is come into a situation and
say, I got all the right answers.
No one's gonna.
Listen to you.
So you've been hired for aspecific reason 'cause of your
background skills and experiences.
Your opportunity is to figure out howto, and I can tell you examples where
I failed in this, but as you come in,like what are your initial hypothesis?
(21:50):
So a data assumptions hypothesis.
The last part was one thing that I found,i've developed over the, I don't know,
the last 10 or 15 years is I tend to beas you can probably tell, I, I talk fast.
I think fast.
I move fast.
People can feel like I'm beingtransactional in my interactions.
Like I tell people I try to buildwork relationships through the work.
(22:13):
What I found was critical is in the first90 days is just to spend time laughing.
What I mean by that is go have acoffee, go have a lunch, make sure you
have enough time where you're doingdinners, where there isn't an agenda.
I. My, my executive team willtell you the ones that I've had.
They, I'll show up at dinner with booksand I'm handing out to people and saying,
(22:33):
Hey, let's talk about this book today.
And they're like, Randy, why don'tyou just chill out and talk about kids
and what did you do on the weekend?
Yeah.
And it's just, it's super hardfor me to do that 'cause I'm
so excited about the work.
Yeah.
But that laughing componentwhere you're being very real.
And laughter brings people together.
It's joy.
And so you're being joyful at a timewhere a lot of people are probably
(22:55):
anxious that there's a new CEOstarting and is their job secure?
What's happening with the company?
So that four L tour over thefirst 30 days is wicked important.
And you can get consumed with, a bunchof little stuff that's that seems
like it's critically important, but ifyou're not making the time to get to
know the people, to try to understandthe core issues, then as you move into
(23:17):
the next 30 days, so day, 30 to 60 nowyou gotta tee up a couple of things.
You gotta tee up some quick wins.
You gotta, in my opinion, you gottafind the things where you can make a
decision where people may have not madea decision in the past and they are
waiting to see if you're gonna do it.
And one example, I was at thecompany and they had a HR leader
(23:38):
and she was fine, nice person.
But everyone thought thatshe wasn't effective.
And I showed up and, in the first 30 daysI was like, God, I need all this help.
And it's not happening.
This person is not delivering.
And so in 30 days I said,look, this isn't gonna work.
We need to move on.
And so I had a bunch of HR professionalsin my background that I've worked
with who have been superstars.
(23:59):
If you're trying to come into acompany and lead transformation,
it is a culture change.
And you need a, you need anHR partner that can do that.
And so I, I let the person go andall the executive team was like, wow,
we didn't think you would do that.
And it's why not?
And they're like blah, blah, blah.
And I was like, look, like it seemed likeyou were telling me this wasn't working
and no one was solving this problem.
(24:19):
I will make that decision.
And I had enough data pointsover the first 30 days to say,
yeah, this isn't working for me.
If it's not working for them, if itwas working for them, then I would
probably take another 30 days andsay maybe I need to tune my radar
a little bit more here because it'sworking for these people, but I don't.
Something's dissonant for me.
So anyways, I think you makethose quick decisions, quick wins,
(24:43):
initiate some programs, do somethinggood in that day, 30 to 60, and
start to build out a a roadmap.
A roadmap for the set of changes youwanna initiate, the set of programs you
wanna put in place the types of thingsyou're thinking broadly on strategy.
And so by the end of 90 days, you'vemet the people, you've learned a
bunch, you've got some quick wins,and now you can take a breath.
(25:05):
Oh, that's excellent.
Thank you so much for outliningthat whole game plan and the
relationship is a crucial part of it.
Sometimes as professionals or when we'reinfused with what we know and how we can
help people, we get really passionate ashuman beings, and I can relate to that.
When I work with individuals for theinternal mindset transformations I get
(25:28):
really enthusiastic, about this wholeidea and what can happen in their life.
So automatically.
I just want to do, likeyou mentioned, yeah.
Bringing the books right.
Yeah.
And I lose that part butoverall I'm really good at the
relationship side of things.
Just having fun, the laughter part.
But when it comes to that, Ijust, something shifts in me.
I'm just there focused.
(25:49):
But the funny thing is I shouldhave more of that in there as well.
That relationship should continue.
The laughter shouldcontinue incorporate in it.
But to your point it's sometimes.
Automatic.
It's just automatic because ofthat level of passion you have.
Yeah.
I'll give you one lesson learnedfrom Maxo was the I don't everyone's
(26:10):
probably familiar with Myers-Briggs orIntacct or insights or discs or the,
all these personality tests you cantake, and I think there are wonderful.
To use at companies I describe 'emas a year's worth of one-on-ones.
If you take a personality test,the ones I use most mostly
is called insights profiles.
I have a specific insight profile.
You have a different insight profile.
(26:31):
Your ability to you.
Use those and now you can, oryou can load 'em up into chat
GPT and I can load your profile.
I can load my profile and say,Hey, I want to talk about subject
X. Help me better frame thisknowing our two different profiles.
So I, that's a total recommendationfor people if you really want
to get to know 'em, is use thoseinterpersonal use those person that.
(26:52):
Prior, and you would haveeverybody's team on the wheel
and you'd see how they resonated.
They were either more creative,they were more like driven, they
were more detail oriented orthey're more relationship oriented.
Those are the four buckets was my teamwas very relationship oriented and so
when me coming in as super hard driving,it felt, intimidating and transactional.
(27:13):
And so we had something called a roundof good at the beginning of our executive
team meetings for the first 15 minutes.
It was not about business.
It was about, Hey what happened in yourlife over the weekend and what do you want
what good thing happened in your life?
And I'm sitting here like fighting Mike.
Fingers because all I want to do isget into the business and instead we're
(27:33):
talking about kids and dogs and vacations.
I could see that, oh my God.
However, having said that, being in ahybrid work environment, giving a little
opportunity for us to laugh to, to builda relationship, a built stronger bonds.
And trust with that team so that thenwhen we started to get into the harder
(27:54):
conversations around the business,we are operating from a place of
where we've already leaning in to therelationship versus showing up and
being on the defense or the offenseas you're taking, sales guys can play
marketing, playing about sales, likeyou de power the intensity and instead.
(28:15):
Empower the relationship.
Randy, that's great, I know whatyou're talking about that level
of go go, but you still have thisunderlying calmness about you.
There's this.
This feeling of, yeah, it'sgonna be fine, kind of thing.
That's what I'm getting from you.
Is that a kind of feedbackyou get from people?
(28:35):
Yeah, I think so.
I think the feedback I get, it isusually along a couple dimensions.
But one thing I would say is havingbeen in the military, what I tell people
is look, no one's in corporate sector.
No one's dying here.
This isn't like in death decisions.
So like it's all just ratcheted,this just relax, just relax.
Number two, I've been working onmyself for 20 something years and
I was a whole lot more intense.
(28:56):
Good.
When I was younger.
Yeah, I would make acouple recommendations.
There's just broadly therapy.
Yeah, there's a great organization outthere called pathwise leadership.org.
Pathwise leadership.org.
And I've been in that programfor, I don't know, 12 or 15
years I've helped lead cohorts.
It's incredibly powerfuland it roots in great.
(29:16):
How do you be present and how doyou interact with other people?
It's tied in beautiful with psychology.
And so it's just, it's super cool.
Great.
So that allows you to have some space.
Perfect.
But I would say in meditation, havingmeditation helps settle everything down.
I do.
You
meditate?
I do.
I wax and wane with it.
(29:37):
Yeah, things are super intense and I'm notgetting a lot of sleep and I'm traveling.
My meditation turns into a nap.
But like this morning I gotup and meditated and I'm just,
I think it that was great.
Helps you be present, beconscious about your body.
Yes.
It helps you create a space,I think if whatever meditation
you're doing, but like gratefulnessfor what you have in your life.
(29:59):
And again, I think you're settingthe conditions for the day if
you're brilliant, deliberate,and intentional about it.
It can really I think it canplay forward throughout the day.
Yeah.
And now you can get, tossed and turned andbeat up by different things and surprises.
And if you can bring yourselfback to, being present.
And thus makes all.
(30:21):
Yeah.
And in a way, what meditation does, ittrains the mind to be a specific way,
for example, you mentioned being present.
Yeah.
And that comes from the calmness, right?
Yeah.
And I practice meditation alot, I worked on creating the
meditative state habitually.
So meaning in each moment, thenI started allowing content to
(30:45):
come in that present moment.
So working on things, actiontaking from that place Yeah.
Of presence.
And then I started getting better atthat, then I started incorporating it
more and more into day-to-day life,
yep.
And then slowly it starts becoming you.
You start becoming thatspaciousness or that stillness.
Yeah, and it's a game changer becausenow life is not this troubled thing
(31:09):
oh my God, what am I gonna do?
It becomes a joyful thing.
Now you're in a flow state where, yeah,good and bad is coming, but you understand
more because you're more expanded.
You.
Awareness, the consciousness more expandedwhere you are allowing things to unfold
rather than why did this happen to me?
Yeah.
So I really appreciate meetingyou, it was great talking to you.
(31:32):
Definitely keep in touch.
Sure.
If there's anything happeningin the future, let us know.
Yeah sure.
If people are interested in learningmore, so I've written, I'm working
on a book, it's called The EightSecrets of Success for SaaS CEOs.
So it's primarily focusedon software as a service.
You can find a lot ofthe chapters on LinkedIn.
And then I literally just launcheda CEO advisory service called CEOX.
(31:56):
Io and so I'm working with a coupleof companies right now, but if people
are interested in more of this andtrying to figure out if they need a
CEO coach and if I'm the right guy, andto your point with the right energy,
yeah.
Come check me out, Randy CEO
x.io.
Awesome.
Love it.
Thank you so much, Randy, and yeah, that'sa great thing about podcasts because
(32:19):
you get the audio side of the energyand the video as well, and depending
on the kind of show you go on, but mostof them now are both video and audio.
Yeah.
Yep.
Is just being you, you just beingyou and talking and that there is,
there's people searching for help.
Yeah.
And there's so many options, so manynews by you making the decision, going
(32:39):
on podcasts is one of the most importantthings you can do to elevate your career
and your network and everything else thatcomes with it, especially relationships.
That's why I love this, right?
Because I get to meet people and build.
Yeah, totally.
That's what I loved about my
podcast.
It was just the conversation you'rehaving, the people you're meeting,
finding out about their lives.
So thank you for the opportunityto be here and you my pleasure.
(33:02):
Wish you the best
Popular Podcasts
Bookmarked by Reese's Book Club
Welcome to Bookmarked by Reese’s Book Club — the podcast where great stories, bold women, and irresistible conversations collide! Hosted by award-winning journalist Danielle Robay, each week new episodes balance thoughtful literary insight with the fervor of buzzy book trends, pop culture and more. Bookmarked brings together celebrities, tastemakers, influencers and authors from Reese's Book Club and beyond to share stories that transcend the page. Pull up a chair. You’re not just listening — you’re part of the conversation.
On Purpose with Jay Shetty
I’m Jay Shetty host of On Purpose the worlds #1 Mental Health podcast and I’m so grateful you found us. I started this podcast 5 years ago to invite you into conversations and workshops that are designed to help make you happier, healthier and more healed. I believe that when you (yes you) feel seen, heard and understood you’re able to deal with relationship struggles, work challenges and life’s ups and downs with more ease and grace. I interview experts, celebrities, thought leaders and athletes so that we can grow our mindset, build better habits and uncover a side of them we’ve never seen before. New episodes every Monday and Friday. Your support means the world to me and I don’t take it for granted — click the follow button and leave a review to help us spread the love with On Purpose. I can’t wait for you to listen to your first or 500th episode!
Dateline NBC
Current and classic episodes, featuring compelling true-crime mysteries, powerful documentaries and in-depth investigations. Follow now to get the latest episodes of Dateline NBC completely free, or subscribe to Dateline Premium for ad-free listening and exclusive bonus content: DatelinePremium.com