Latest / Scrappy but Successful [Consultant's Personalities When No One's Watching] / 41. The Owl Point Story: Scrappy Consulting Wisdom with Mark Masquelier

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41. The Owl Point Story: Scrappy Consulting Wisdom with Mark Masquelier · Scrappy but Successful [Consultant's Personalities When No One's Watching]

• 0:00
  What's happening, everybody? Welcome to Scrappy But Successful. It's a show where I sit down
• 0:04
  with your favorite consultants and we find out if they're successful today because they're sophisticated
• 0:08
  or because they're a little bit scrappy. I'm your host, Jack Tompkins, CEO of Pineapple
• 0:12
  Consulting Firm and Pineapple Analyst AI, always helping small businesses become more data-driven. Fun fact
• 0:16
  of the day, we got we got an Oceanside California resident on. So I did
• 0:21
  some digging. Oceanside California is home of the Top Gun House. It's the famous movie,
• 0:25
  the original, of course. it's still there today and is now a famous dessert shop.
• 0:29
  Not necessarily that fun, no data in it, but I just love that movie. So
• 0:33
  I figured I'd share it. But that's neither here nor there. Today I'm joined by
• 0:38
  my friend Mark Maskelier. He's the founder of Owl Point. He's a fractial CFO, he's
• 0:42
  a fractial C OO, and he's a he's a strategic advisor of what he does.
• 0:46
  So the guy knows what he's doing. Highly qualified, he's been an executive, he's got
• 0:50
  extensive experience navigating business growth. He does it through things like financial planning, cost-saving initiatives,
• 0:55
  profitability, and the biggest one, at least in my opinion, strategic organization and f and
• 0:59
  then the efficiency around that. So, Mark, man, I am so excited to talk with
• 1:03
  you. Thank you so much for coming on. We know that you're successful, but the
• 1:07
  question we have for you today, do you think you fall more on the sophisticated
• 1:12
  side or more on the scrappy side?
• 1:14
  Thanks for the welcome, Jack. And I'll I'll get to that in just a few
• 1:19
  seconds here. back to the Top Gun house. I it's about three miles away, five
• 1:24
  miles from my home and office. And it is non-stop attention. They've moved it twice.
• 1:30
  Oui.
• 1:31
  and it's a fun little spot. I think they still have the motorcycle out front
• 1:36
  there. but but yeah, it's it's it's one of my almost every weekend down off
• 1:42
  the Boardwalk there in Oceanside. Great, great research there. So scrappy, sophisticated. So sophisticated on
• 1:48
  the outside, scrappy on the inside is if I if I had to pick, it'd
• 1:54
  be my my style, my my real me is scrappy, but sophisticated in terms of
• 2:00
  kind of how I tend to present. I came out of the CPA world. I've
• 2:06
  been licensed for for several decades and so a very sophisticated kind of formal world.
• 2:12
  That said, in that world, in that context, I was definitely in the scrappy bunch.
• 2:18
  I was thinking outside the box a lot. and and so and and I was
• 2:24
  just thinking about when I was thinking about that, I was like, okay, scrappy mark,
• 2:30
  how do I portray this? So here's a little example. when I moved to
• 2:36
  Yeah, what do we got?
• 2:37
  when I moved to San Diego, I bought like a 50 foot RV rig. I
• 2:42
  had a a big diesel pusher pickup truck, just bought it, Silverado, and I bought
• 2:48
  a 30 foot travel trailer. and I was like, okay, cool. I got this dialed
• 2:53
  in. I'm gonna, I'm gonna make the move. And we we still had our home
• 2:59
  in in in Tucson. And about six weeks in, I'm camping out in Santee. It's
• 3:04
  about a little inland west from here. It's actually desert. And and about Week four,
• 3:10
  I just was completely overrun by ants. and like like woke up in the morning
• 3:15
  and there was antrails, like thousands of them going through my trailer and I was
• 3:21
  like, okay, maybe I
• 3:23
  That's terrible.
• 3:23
  don't quite have this dialed in. I was humbled. I was like, okay, and and
• 3:28
  so we lasted there about six weeks. Then we moved to Mission Bay, which is
• 3:34
  right on the water, right at the ocean, and then Pacific Beach. And then La
• 3:40
  Jolla, and then Carlsbad, and then finally where I'm at now in Oceanside. my wife
• 3:46
  says we moved like seven times in six years. I I still maintain that those
• 3:52
  were just extended vacations. you know, priceless places every people want to live. The three
• 3:57
  or four were right on the water. there was definitely some stress. so but But
• 4:03
  it kind of the scrappy side of me. It's it's like I just packed up
• 4:09
  and loaded up into a a a a trailer and it got it, you know,
• 4:15
  and and we lived and we lived out of that for three months. So that's
• 4:21
  kind of a more of in terms of scrappy, sophisticated that that little tells a
• 4:26
  little bit more about my true nature. So
• 4:30
  Yeah. I that is that is very scrappy. But also I I totally respect the
• 4:33
  move. You gotta there are cool places to live and you got to test them
• 4:36
  all. It's you know, there's there's kind of ways to look at it.
• 4:39
  Well
• 4:40
  Are you a surfer? Are are you out there surfing at all?
• 4:43
  Absolutely not. I tried
• 4:45
  Okay.
• 4:47
  and then because I th I'm like, I was a water skier, I was a
• 4:51
  snow skier. this is just a big snow ski or a you know or something
• 4:56
  and and I couldn't even stay balanced on the board. And and and
• 5:00
  jeez.
• 5:00
  and and and I've read a lot since I still have a wetsuit, I got
• 5:05
  rid of the surfboard. I still wanna do the to get get out there, but
• 5:10
  I I do I need to go take a lesson is what it kinda comes
• 5:15
  down to. but
• 5:16
  Okay.
• 5:17
  I love the water. We started boating just this year. so I'm I'm out on
• 5:22
  the water and and and and and I love riding my my bicycle down there.
• 5:28
  We'll you know, we'll we'll cook out at the beach quite a bit, make some
• 5:33
  make some burgers and fries and so. but we we're I I'm definitely water people.
• 5:39
  W I'm about three miles from the ocean. just enough inland to be not in
• 5:45
  the the the the closer part to the inland is usually very busy. And also
• 5:50
  that strange interestingly if if coastal living we learned this, that was part of the
• 5:56
  seven moves. is that the first mile or so by the ocean tends to be
• 6:02
  very it's called an inland layer, but it tends to be very Foggy, cloudy a
• 6:07
  lot where the
• 6:09
  right, right, right, yeah.
• 6:10
  where the temperature kinda hits. And so we we I met a a good friend
• 6:15
  now or who person who's now a good friend who was lifelong in North County,
• 6:20
  San Diego. And she's like, you just gotta move in then three miles. So so
• 6:25
  we we we've settled in here now. So how how about
• 6:29
  Nice.
• 6:30
  you, Jack? Do you are you I know your east coast, do you do ocean
• 6:35
  life or but skirt surfing or any
• 6:38
  I I'm on a lake, so I've I've become more of a lake guy, but
• 6:41
  growing up in Connecticut, we were close to like Long Island Sound and stuff. So
• 6:44
  I've I'm always a huge water guy. I even got like my whatever, my beach
• 6:47
  surfing shirt on and spirit of oceanside today. It's making me look real sunburnt right
• 6:50
  now, because I am sunburnt.
• 6:51
  Nice. Nice. I love I love the look. Yeah. What so you're
• 6:58
  But yeah.
• 6:59
  you're on a l yeah, I I most of my before ocean before moving here
• 7:03
  ten years ago, I did a lot of inland boating. so lakes and rivers and
• 7:08
  so so you
• 7:09
  Yeah. Yeah.
• 7:11
  s do you s water ski, do you jet ski, do you
• 7:16
  I I kay these days. I I'll I'll rent
• 7:17
  Hi, nice.
• 7:19
  a boat with some friends and I'll go out kayak, but that's that's all I
• 7:24
  can afford as a poor entrepreneur.
• 7:26
  I get it. I get it.
• 7:28
  where are you originally from? You said you moved from Tucson. Did you start in
• 7:32
  Tucson? Did you where did you have a lemonade stand? Any entrepreneurs of the family?
• 7:37
  so yes, I mean to the last and so I started out in Chicago, suburbs.
• 7:43
  Okay.
• 7:43
  I was born in the suburbs, south sub southwest suburbs of Chicago. And I started
• 7:48
  at Pricewater House in downtown Chicago. It's now PWC, top three international CPA firms. And
• 7:54
  in my late twenties I'd kind of gotten tired I liked it when I was
• 8:00
  a little younger but kind of the the weather was I'm like, okay, I could
• 8:06
  use warmer. And so I went I went a little too far to the extreme.
• 8:12
  I went to Tucson in in my late twenties and you know that's like 112
• 8:18
  in the shade.
• 8:20
  Oof.
• 8:20
  and and so but I had a I have a lot of family there and
• 8:25
  so I kind of ended up being there for a few decades and then As
• 8:31
  friends sometimes remind me, I I did it backwards. Most people retire in Tucson. I
• 8:36
  I moved from Tucson to to to eventually you know to settle in in San
• 8:42
  Diego. So they you did it backwards. I'm like, well, that's kind of the story
• 8:47
  of my life. I I learned things and that's that just you're entrepreneur. I I
• 8:53
  have my definitely siblings who are all very entrepreneurial. Interestingly. And and like my my
• 8:58
  father was very traditional. He was IBM. talking with you know, knowing your background a
• 9:04
  bit. I mean he was he was an engineer at i at IBM, but not
• 9:10
  college educated, just self-taught in IBM trained him, but he did real well. and he
• 9:15
  always had an an entrepreneurial spirit. I don't and I don't know where we got
• 9:21
  it from, but me and both of my b brothers And one of my sisters
• 9:26
  or six of us or all are in our own businesses. Six of us, yes.
• 9:32
  It was
• 9:33
  There's six of you. Oof.
• 9:37
  it was the Brady bunch, Jack. And liter literally
• 9:40
  Yeah.
• 9:40
  there's three boys, three girls, and pretty close in age. And and so that's a
• 9:45
  little bit I think of perhaps why we became entrepreneurial, 'cause the house was very
• 9:51
  busy and we wanted to get out and do things. So
• 9:56
  You must have gotten some good I know you did a a brief stint in
• 9:59
  stand up comedy as well. You must have had some good bits about the Brady
• 10:02
  Bunch and stuff.
• 10:03
  I di I did. I well I didn't I didn't stick with it too too
• 10:09
  long, mostly because I was like, Well, I need to make some money. I I
• 10:16
  Yeah.
• 10:17
  took I basically took a summer off and did did that. I did a
• 10:20
  Okay.
• 10:20
  I did a two month workshop and then the graduation was a show to essentially
• 10:25
  a s I mean to a sold out it was all our family and friends
• 10:30
  from the from the people in the show but s full house at and at
• 10:35
  laughs and Tucson. And then but but y you could you can see it based
• 10:40
  on on this, but my my stage name was Baldmark. And
• 10:44
  Okay.
• 10:45
  and so and and it's just like, you know, some people don't want to talk
• 10:48
  about that. I'm like, well it's kind of obvious, you know, we can
• 10:52
  Yeah.
• 10:53
  you know it it and so and it's it's always been a kind of a
• 10:59
  funny part. But I didn't really have any bits on that. but going back to
• 11:05
  the entrepreneurial very at a very young age. my gosh, I'm just trying to think
• 11:11
  through the kind of the beginnings of this. I was I delivered newspapers, I was
• 11:17
  a caddy, I was I I I worked in a in a c at a
• 11:23
  gas station, I worked in a car wash, I I cooked steaks at a restaurant,
• 11:29
  and all this was before the age of eighteen. And and and so I was
• 11:36
  just always looking for something new, excuse excuse me, something new, something fun to do.
• 11:42
  And and so I think a lot of it probably came from my dad. He
• 11:48
  he very much encouraged us to to probably do what he never had the chance
• 11:54
  to do with six kids. he he was very busy and needed to have the
• 12:00
  you know the the steady work and all that. but he encouraged all of us
• 12:06
  to kind of explore and find our our our our joys. And so I tried
• 12:12
  a different a lot of different jobs. and I mean I you know the independence
• 12:19
  that came with the the the the the work and and having a little bit
• 12:25
  of money I think was the the foundation and for for the entrepreneurial spirit in
• 12:31
  me. I actually went into accounting I was real good at real s strong with
• 12:37
  numbers and math. but I one of the big drivers was I wanted to see
• 12:43
  how other people ran their businesses from the inside. And so the the accounting path
• 12:49
  got me exposure and it in by by my mid twenties to probably fifty different
• 12:55
  businesses where as the accountant you you get to see it you get to see
• 13:02
  the the insides and and there was a there was a handful of folks who
• 13:08
  were like C suite level. These were smaller million dollar, couple million dollar companies a
• 13:14
  lot of times, but up up to the twenty five, fifty million. But people who
• 13:20
  would be like, hey, let me teach you about this or let me, you know,
• 13:26
  I would help them with numbers and they'd they'd kind of open their doors. So
• 13:32
  but the but the entrepreneur spirit in me resurrected after three years at PwC. four
• 13:38
  five years actually I was interimed as a controller. So I went out I went
• 13:45
  out on my own in consulting, basically. And and so for the last several decades
• 13:51
  since I've been primarily in consulting. And I sometimes I've taken job employment jobs for
• 13:57
  clients because it was you know, they just they needed They wanted somebody and then
• 14:03
  what that became over the years, it morphed into what I do now, which is
• 14:09
  instead of a few years, I can usually accomplish in six months through fractional. It
• 14:15
  and sometimes fractional morphs into interim. in other words, I'll take on the whole role.
• 14:21
  and it's almost full time like twenty, thirty hours a week. but it's short term.
• 14:28
  I'm helping them build a team. I'm you know, in the in my earlier years
• 14:34
  it was I guess nice for the ego that people would be calling me years
• 14:40
  later and saying, hey, what about this? What about that? And and I've since realized
• 14:46
  or decided, maybe really better framing that I wasn't building teams for them. I wasn't
• 14:52
  helping them be on their own. I wasn't helping them build systems and structures and
• 14:58
  processes that they could grow without me. a lot of times it both with with
• 15:04
  with the my peers that I work with, other s other contractors and with clients,
• 15:11
  I use the analogy of your child going off to college. It's it's like, you
• 15:17
  know, you y y y you want them to be independent. You know, you just
• 15:23
  s so so that that's more I mean that that's kind of what got me
• 15:29
  from entrepreneur to few years as employees intermittently to just full fractional CFO and COO.
• 15:35
  And then the the COO came in the last decade or so, maybe 10 to
• 15:41
  maybe 15 years, because so much of my finance accounting work was I was leading
• 15:47
  me to consult clients about broader operations. hey, what about this process? Hey, can you
• 15:54
  help us find just a report you know, a full-time CFO. hey, can you help
• 16:00
  us with our systems? Hey pe looking for people like yourself, Jack, who who are
• 16:06
  just love of data, you know, just somebody who just, you know, can can help
• 16:12
  us you know build out IT, but the operations, so I so I morphed into
• 16:18
  IT, HR, HR, I I I I contract, I subcontract. really just f you know,
• 16:24
  refer mostly to specialists. But the IT I'm strong in. Was writing code since I
• 16:30
  was a teenager. so so
• 16:33
  You got it all going. Okay.
• 16:36
  that's sort of the morph from CFO to C O O. And then I've held
• 16:41
  a s I've held a couple of CEO positions, but interestingly what I learned is
• 16:47
  I'm I'm I'm I I enjoy and I'm you know, I'm I'm real strong at
• 16:53
  kind of being that support for the CEO and the board. So for the most
• 16:58
  part, I mean, I'd say exclusively really n anymore, 'cause I can I can just
• 17:04
  I can figure it out early on. I work with CEOs who see that value
• 17:10
  and who are not you know, I'm I I'm not looking for their job. I'm
• 17:15
  you know and
• 17:17
  Yeah.
• 17:17
  And then and then a lot of both of those jobs, especially the CFO, it's
• 17:22
  kind of a dotted line to board of directors. they they we I I always
• 17:28
  want them to know that if I really disagree, I'm gonna speak up to them
• 17:33
  directly. And and that's sometimes challenging if I don't have a strong relationship with the
• 17:39
  CEO, you know, that sort of the agree to disagree, but let's find a a
• 17:45
  middle. So so short version is that's a lot of where I focus now is
• 17:50
  consulting with CEOs and boards. And
• 17:53
  Okay.
• 17:54
  and I and I and I just love it. So but anyway, I went on
• 17:58
  for a long time. Thanks for leading me down that discussion.
• 18:02
  That's what we're here for, man. you mentioned something in there, the kind of the
• 18:07
  the CEOs that see the value in it. As consultants, we're often looked at as
• 18:12
  when expenses get tight, the consultants are among the first people to go. It doesn't
• 18:17
  seem like you've had that, or at least you've avoided that in your career, presumably
• 18:23
  very strategically. How do you continuously prove value? Like, are there specific success metrics that
• 18:28
  you're tied to? How does the CEO know that you're continuously proving value?
• 18:33
  It's a great question. I I live that weekly with every CEO. I'm indirectly sort
• 18:39
  of produ or or supporting my value in my weekly meetings, usually a half hour,
• 18:45
  sometimes an hour with CEOs. And I'm always talking about what's going on, what we're
• 18:51
  doing, where we're headed, and one of the biggest landing points and it wasn't I
• 18:57
  didn't it took me a while to figure this out, quite a while. is I'm
• 19:03
  always talking about how you can replace me. And and and some CEOs were like,
• 19:09
  no, I want you around forever. And like, okay, well, I can, you know, two,
• 19:15
  three, couple hours a week, that's good, but but you know, I I you can
• 19:21
  get better, I mean you can get somebody less expensive that's your direct employee, even
• 19:27
  if they're a part time employee. So so I in a in a way I
• 19:33
  describe it as I spend their money like it's my money. So I'm not looking
• 19:40
  to be a fixture in your organization. And I think that resonates with them in
• 19:46
  terms of value. and then I use I use the numbers and budgeting and particular
• 19:52
  forecasting to to kind of support what we do. And then sometimes it it becomes
• 19:58
  like, my gosh, you know, you're expensive. And I'm
• 20:02
  Yeah.
• 20:02
  And in in terms of consultants, I'm not. but the hours can build up. And
• 20:07
  so another big piece often is I it it it's a it's a it's an
• 20:12
  investment in oftentimes cleaning up a lack of investment in what I do for many
• 20:18
  years. And so there's this hump of expense to to get things caught up. I
• 20:23
  mean, I was working on a client today. We're cleaning up their their their fixed
• 20:28
  assets, their property and equipment. And nobody's done this for 40 years. I mean they
• 20:34
  have they have, you know, it's just, you know, it's it's so so so the
• 20:39
  balance sheet, you know, we have all these fully depreciated assets sitting there. It's a
• 20:44
  little too much into the weeds, maybe. but I have a treasurer who's like, What
• 20:50
  is all this stuff? He's he's very outspoken. And and so we did a very
• 20:55
  thorough analysis for them. so but that that's another part of I'm always I'm always
• 21:00
  justifying it, what we do weekly and planning at the same time. And I I
• 21:06
  think it's a differentiator in how I do consulting. There's a qu there's a fair
• 21:11
  amount of I mean there there's a lot, I think, and you know, that that
• 21:16
  are looking to be sort of around for the long term. And and I and
• 21:22
  I tell clients from the beginning and throughout, I'm I'm not looking to that. And
• 21:27
  and when they say it's expensive, I I usually say, Yeah, you're right. I I'm
• 21:32
  not gonna disagree. So how do we solve that problem? You know
• 21:37
  Right.
• 21:38
  don't don't become the, you know, don't become part of the problem. Help them solve
• 21:43
  that problem. And so
• 21:45
  Okay. So as the finance guy who's making forecasts and justifications every week and stuff,
• 21:49
  this is a question I'll ask us a decent amount. Have you ever had to
• 21:53
  do the credit card game for yourself or your clients where you wait till tomorrow
• 21:57
  to charge something 'cause that's next month's statement? Or are you more it's all part
• 22:01
  of the budget, it all kind of works its way out in accounting?
• 22:05
  I I don't do that at all. it's
• 22:07
  Okay, nice.
• 22:10
  it's very straightforward hours and there's sometimes I'll put out an invoice and I'd be
• 22:15
  like, that was a lot of hours. Then there's sometimes I'll I'll go, there was
• 22:20
  a lot more value than the hours that I build. And so my early foundation
• 22:25
  taught me that. I mean, a a lot of it's I don't wanna say it's
• 22:30
  unethical, but it's sort of the ethics and morals that I was taught. I mean
• 22:35
  early on is through my my my father in particular. and then certainly the the
• 22:40
  the PWC days, it's just, you know, you just you y you just kinda do
• 22:45
  what you need to do and and it let the cards land where they may.
• 22:50
  I remember a story one PW guy said back then, he said, Well, if I'm
• 22:55
  thinking it's just we're we're probably talking o over over dinner or something. Well If
• 23:00
  I'm in the shower and I'm thinking about a client, do I bill that time?
• 23:05
  So we have
• 23:07
  Yeah.
• 23:09
  this debate about, you know, do you do that? Well, it's not just desk time
• 23:14
  because
• 23:15
  Yeah.
• 23:15
  us, you know, thinkers like ourselves, we're we're always thinking about it. So it's like,
• 23:20
  you know, but the short answer or the short conclusion I took away was no,
• 23:25
  you don't bill for that time. You know, that's that's sort of professional growth and
• 23:30
  you know. but but it's great great question. and then some I I've I've wrestled
• 23:35
  with on occasion I'll do to to sort of solve that, I'll do retainer, like
• 23:40
  non ref fixed fee, if you will, really not retainer, but fixed fee. But I
• 23:45
  find that has more problematic dynamics. I put in a lot of hours and I
• 23:50
  didn't get paid or the client says, you didn't do much this month, but I
• 23:55
  still you know. So it it's I i I think it's consist I think the
• 24:00
  approach I take is consistent with how I advise clients. It's like just always look
• 24:05
  for the value and and you know, across the board. I mean board of directors,
• 24:10
  you know, hey, I have a board member who's, you know, maybe not delivering. Okay,
• 24:15
  let's let's look at that. I have a C suite person who's not that's you
• 24:20
  know, or is let's look at that. And so i I I just look at
• 24:25
  myself as an extension of the same conversation. It's just, you know. So that's a
• 24:30
  great question. I don't think I've ever heard that question. I think about it a
• 24:35
  lot, but I don't think anybody's asked me.
• 24:38
  Okay. for your own business, getting clients for your own business. Any scrappy marketing moves
• 24:42
  like you know, zero budget marketing campaigns where you're printing flyers at home. I know
• 24:46
  you were you were in a radio show at one point too. Give me give
• 24:51
  me some of the scrappy marketing that you've had to do for yourself.
• 24:55
  wow. Yeah, great question. gosh, in the early days, this'll date myself a little, but
• 25:00
  this is all pretty much pre-digital marketing. This is phone books and flyers era. I
• 25:05
  know that's hard for a lot of people to relate to.
• 25:10
  Nice.
• 25:13
  and I would print flyers and I would literally either go door to door, I
• 25:18
  would go door to door with business to businesses and just you know, just pure
• 25:24
  old school cold call, but just go down the street and just introduce myself and
• 25:29
  I had a a handful of flyers and and maybe some business c probably some
• 25:35
  business cards in my pocket. and and then and then in the in the mo
• 25:40
  in the modern area, I I grew up with digital marketing. So like in the
• 25:46
  late nineties I was I had a a It was a retail business, retail wholesale
• 25:51
  that I was part owner in. And and I and it introdu I I I
• 25:57
  learned digital marketing through that. And and one of the scrappiest things was I found
• 26:02
  they're still they're they're common now, but there wasn't like maybe one dashboard where I
• 26:08
  could manage all of my digital marketing through that single channel. Like I could write
• 26:13
  the
• 26:14
  Right.
• 26:14
  ad and then hit send and it would push it out to thirty or forty
• 26:19
  media outlets. And so I was I was real happy I was real excited about
• 26:24
  my s you know, finding that then and now it's you know it's commonplace. but
• 26:29
  the I mean it's it's it's more common, but but those are a couple of
• 26:35
  things in the in the different eras. So
• 26:38
  Okay. Okay. and and the radio show, I gotta I gotta pry into this. Yeah.
• 26:41
  Yeah. Yeah.
• 26:42
  the radio show, yeah. So I let's see, this was During the mid aughts crash,
• 26:47
  six, seven, I I was looking for a little side gig, as we call as
• 26:53
  it's called now. But and and and one of my clients sold mortgages. He's like,
• 26:58
  You'd be really good at this. Like, okay. You know, do I have to go
• 27:04
  to an office? No. Can can I, you know, he goes, You know the numbers,
• 27:09
  you're real good at you know, you're you're You're you liked people, you're connected. Okay.
• 27:15
  So I started selling mortgages, essentially a mortgage broker. and I was it became focused
• 27:21
  on commercial mortgages. but anyway, the the the the head of the the owner of
• 27:26
  the brokerage firm was looking for new marketing and he he he decided he wanted
• 27:32
  to do a Saturday morning radio show. And he had about Most all were senior
• 27:37
  to me, but about twenty brokers and nobody wanted to do the show with him.
• 27:43
  They're like, No, no, I don't I I don't I don't wanna go on radio.
• 27:49
  I don't wanna be a you know, they you know. And I was like, I'll
• 27:54
  do it. And so we we just I mean, he was the lead, he had
• 28:00
  he had deep industry experience. I was sort of the the the the colour or
• 28:05
  the ask dumb questions guy and and they they they were dumb because I didn't
• 28:11
  know the answers a lot of times.
• 28:14
  Genuine questions. Yeah.
• 28:15
  Anywhere. Yeah, on on an yeah. And he'd be like, well let me tell you
• 28:20
  about that. And so I was learning a lot from it, but we did that
• 28:25
  for six months. one hour recording every Saturday. And it started generating, I don't know,
• 28:30
  five to ten leads every every Saturday. We would have s we would have people,
• 28:35
  usually two one or two in the office, be like, Hey, we have you know,
• 28:40
  call we have people who can take you know, and so we could it was
• 28:45
  a very easy thing to measure. And then after six months the other more senior
• 28:50
  brokers were like, I want to be on the show. So I you know, kind
• 28:55
  of kind of kind of stepped out. But and then that and then the stand-up
• 29:00
  comedy was a was a few years later. Actually it was a few years earlier
• 29:05
  now that I think about that. That was a few years earlier. and and and
• 29:10
  it it it kind of capsulizes when I when I told my parents when I
• 29:15
  was in grad near graduation that I was gonna take the CPA exam and working
• 29:20
  accounting, they both looked at me and said, That doesn't sound like you. I I
• 29:25
  I'm I'm I'm more, you know, I I just I I have, I guess I'd
• 29:30
  say a more extroverted, outgoing personality. And so but but it it ended up being
• 29:35
  a real gift because I'm I'm very strong with numbers. and having both as a
• 29:40
  skill set is It's served me well in life, so
• 29:44
  it
• 29:44
  but
• 29:45
  it's important. You gotta be able to take the numbers, understand the numbers, and then
• 29:49
  translate the numbers to people that either
• 29:51
  Yeah.
• 29:51
  don't know as well or don't care about as much, right?
• 29:54
  Right.
• 29:55
  so when do you actually start Owl Point and and how do you come up
• 29:59
  with a name?
• 30:00
  So the the name came from sort of an interesting progression. I actually I started
• 30:07
  out with sort of a boring name. I forget what it was at the no
• 30:15
  it wasn't that boring. but it was something like nondescript.
• 30:20
  Okay.
• 30:21
  and and and and and decades ago, this is my th third. iteration of a
• 30:26
  consulting firm. I had I had one in Chicago and then I wound that down
• 30:32
  and I had one in Tucson and then I wound that down. So so each
• 30:38
  you know each place I've lived Chicago, Tucson, San Diego. and and so and and
• 30:44
  so they they were very nondescript names. And then the the first one I started
• 30:50
  which I did trademark is was was is CFO one two three. And and
• 30:56
  Okay.
• 30:57
  it was like, okay. And and few some people said, that makes it sound simple.
• 31:00
  And I was like, well, that's okay, because that's my goal. I
• 31:04
  That's the goal, yeah.
• 31:05
  I want to I want to make this simple. And then as I moved into
• 31:10
  coo work operations, the the CFO name didn't translate to the whole message. And so
• 31:15
  I I just actually this is just goes back about it. when I rebranded about
• 31:21
  a year now, I used AI. And I just I put in my resume. I
• 31:26
  I I put in the history that I just described and I was like, can
• 31:32
  you give me some suggestions? And and much like with a a lot of AI,
• 31:37
  it took dozens of iterations and and months of back and forth and thinking about
• 31:43
  it. And I ended up settling on I wanted an animal in there. And so
• 31:48
  owl, I like animals. I'm very outdoors oriented. And I needed it I I I
• 31:54
  knew I wanted a a single word. and and and and so I I went
• 31:59
  through some iterations. owl path was one and that had a little too much I
• 32:05
  mean d it it there there's there's some other, you know, so I just I
• 32:10
  so and then just owl point evolved from that. And so and then I used
• 32:16
  my some of my teammates and I was like, what do you think about this?
• 32:21
  What do you think about that? And and this was the one that everybody went,
• 32:27
  I like it. You know, I like owls. I like, you know, and it it
• 32:32
  it can resonate with intelligence, which, you know, it's part of what what what we
• 32:38
  provide as consultants is some, you know, some intelligence that's considered. but a lot of
• 32:43
  it came from just I wanted to pick an animal. I think I was looking
• 32:49
  at some of the other like the gecko kind of world where you you're associated
• 32:54
  with an animal. There was another one I can't remember that came up that was
• 33:00
  animal based. And and so I was like, that's me. I love being outside. I
• 33:05
  I I'm big fan of outdoors. And then and then the point part was sort
• 33:11
  of, I mean, intended to get to the which I'm not doing a great job
• 33:16
  of at the moment, maybe, of getting to the point. you know, it's like how
• 33:22
  do we get you to where you need to be and and you can go
• 33:27
  off, you know, you can be you can be independent and so
• 33:32
  Okay. I like it. I mean, I we were talking about the the pineapple name
• 33:36
  for me and how it's how it's very, very sticky. I think the owl has
• 33:40
  I love it.
• 33:40
  very like a a wise association with it, right? The the the wise owl kind
• 33:44
  of thing. And then the point that's I I almost view it as like, okay,
• 33:48
  this is this is the thing that you have to pay attention to. Like here's
• 33:52
  the one-line summary kind of thing. So here's like the wise version of that.
• 33:57
  Jack pineapple jack as I just shared with you when we're getting
• 33:59
  Yeah.
• 34:00
  ready. I'm like, in my head, he's always you're always pineapple jack. And then you
• 34:03
  shared that that's what everybody calls. Like, cool. I got there on my own, I
• 34:07
  think. but you just you
• 34:09
  Exactly, yeah.
• 34:10
  you just did it, you just summarized very well what took me a while to
• 34:13
  get yeah, it's get to the point. And and and
• 34:15
  I got you. Yeah.
• 34:17
  and and you just did that for me. So thank you. But yeah, yeah, it's
• 34:19
  great.
• 34:20
  course. Let me hit you some lightning round, scrappy versus sophisticated questions. early on, did
• 34:25
  you have any clients that you were like, man, this is gonna be easy work,
• 34:30
  easy money that you ended up losing money on or became a complete nightmare.
• 34:35
  I did several, probably probably
• 34:36
  Yeah.
• 34:38
  more than I try I often want to remember, but yes. I I always took
• 34:43
  the approach, I still do, but early on that if it's not succeeding, it's at
• 34:49
  least part on me. And and then I would look at it as build a
• 34:54
  relationship of of of like a friend almost like, hey, maybe I could have done
• 35:00
  this better and sometimes I would you know, discount my fees or something like that.
• 35:05
  Just I mean, whatever, you know, it it's a two way street. It that it
• 35:11
  comes up a lot in consulting. It's it's like it's not you, it's not me.
• 35:17
  It's something just wasn't working. And so but yeah, there's less of those, but I
• 35:22
  I still have them. I had one recently who what they thought they needed, which
• 35:28
  was a forecast, was really they just needed a whole different strategy. They thought they
• 35:33
  needed a financial forecast. And so I started and about ten hours in, I I
• 35:39
  was like, y y you don't need to be paying me for this. Here's what
• 35:44
  and and then they followed the strategy change. And and they may I mean good
• 35:50
  chance they'll come back to me, but they they shifted they were for profit that
• 35:56
  shifted to a non profit.
• 35:58
  interesting.
• 35:59
  They were the the problem they were solving was a very public problem and a
• 36:05
  very well known problem regarding California fires.
• 36:08
  wow.
• 36:09
  And and and so the funding is is and they're like, Wow, we just you
• 36:14
  know, that's great. And then they started circulating that. So it it but I I
• 36:19
  discounted the fees and I just I s I I I stopped the contract. You
• 36:24
  know, they're like, we're not, you know, so But but yeah, there's there's a whole
• 36:29
  bunch more, but there's a couple that are examples. So
• 36:33
  There's always a few that stick out for sure. But you learn from that's how
• 36:37
  it works. speaking of contracts, do you do a contract for everything and even scope
• 36:41
  changes and stuff like that, they all get a contract addendum? Or are you just
• 36:45
  we're we're doing hourly so it's all gets kind of grouped in together.
• 36:49
  In in between I do a contract for everything. I learned that from the CPA
• 36:55
  world. We're required to have a written contract and and is it and it's always
• 37:01
  it it turns out good practice. Sometimes I'll do SOWs for each phase. sometimes because
• 37:08
  if it's less known what I'm gonna do, sometimes I'll lay out the the the
• 37:14
  stages in a contract and and manage it from there. But similar to the com
• 37:20
  the discussion I was had about justifying and rationalizing and ex cost weekly with CEOs,
• 37:27
  it's it's also always very evolving. And so there it's a it's a trade off
• 37:33
  if it depends on the relationship. I mean, I I have one client now who
• 37:39
  just wants everything written up. And so I actually brought in another consultant. who's more
• 37:46
  aligned that way, because I was spending a lot of time, more than I thought
• 37:52
  they should invest in writing out the plan than it would take to execute parts
• 37:58
  of the plan. You know, 10 page proposal in this case. And I was like,
• 38:05
  you know, w w I mean, and and and I still did some still am
• 38:11
  some consulting with the consultant I handed it off to but just yeah, so so
• 38:17
  somewhere in between.
• 38:19
  Okay.
• 38:20
  but yeah.
• 38:21
  Okay. gimme give me a little in the morning routine. What is the first time
• 38:26
  of day that you allow yourself to look at your emails?
• 38:30
  Embarrassingly, but probably both I it's when I'm laying in bed.
• 38:34
  Yeah.
• 38:36
  it's the phone is sitting right there and alarms, I mean all the noises are
• 38:42
  off. And some days I'm like, don't do it, don't do it. and then my
• 38:48
  my my sort of rationalizing is part of my morning routine is stretching every day.
• 38:54
  So I I'll I'll stretch while I'm still in bed and and
• 39:00
  Well multitasking.
• 39:02
  so I so I can justify that it's okay to look at the phone. but
• 39:08
  anyway, and then most of my
• 39:11
  Yeah.
• 39:12
  my mornings morph from there. But it's I I love what I do, Jack. So
• 39:16
  it's not like work. It's not like,
• 39:19
  Right.
• 39:19
  no, what happened? It's like, what's going on? You know, it's it's it
• 39:22
  Right. Yeah, that's a good way to think about it. It's I mean, that's a
• 39:25
  the same excitement of checking last night's sports scores kind of thing. Okay.
• 39:29
  Yes, yes. Same y i I go you just gave me goosebumps. Same it's just
• 39:33
  like checking sports scores. Yep. It's I'm a
• 39:36
  There you go.
• 39:37
  big sports fan, I know you are also. and yeah. Like
• 39:43
  Yeah. Let's let's stay inside the inbox here. how many emails unread is too many.
• 39:52
  Ten to twenty. I'm
• 39:54
  All right, that's not bad.
• 39:55
  I'm I'm I'm an obsessive, I'll admit it, inbox organizer. and I either archive just
• 40:02
  get it out of my inbox or I flag it and if it's sitting there
• 40:09
  for long flagged and I didn't do something, little little voices start telling me I
• 40:16
  need to do something. I also use it for checks and balances. I have people
• 40:23
  I supervise, more like staff accountants. My opening question is, how many emails do you
• 40:30
  have in your inbox? And it's like, if it's over 200, I'm like, okay, let's
• 40:37
  talk. You know,
• 40:39
  Right.
• 40:39
  I got it under two, you know. So and I I I but but it's
• 40:44
  a pretty low number.
• 40:46
  Okay. Okay. Yeah. That's pretty good. all right, last one here. does your phone currently
• 40:52
  have any cracks or screen issues?
• 40:55
  Ooh, not currently. But it it often i it
• 40:59
  Was it a recent fix?
• 41:01
  it's it seems to be every three or four months something happened. if I don't
• 41:07
  have a backup screen save screen whatever that's called, screen protector, I'm I'm on Amazon
• 41:14
  ordering another three pack, so
• 41:17
  Yeah.
• 41:18
  I don't I don't like to look at a cracked well the it never a
• 41:22
  cracked screen, that would just be Unacceptable, but it's a crack screen protector. I can
• 41:27
  I can it'll last about a week or less until I have
• 41:31
  Yeah.
• 41:33
  anxiety symptoms. But but since you asked for one of the things, I mean it's
• 41:37
  not quite there, but I currently have a case that sort of slips off. I
• 41:42
  guess it's too old or it was just too cheap. And that's really bugging me.
• 41:46
  So
• 41:47
  Okay. How long will it take you to replace that?
• 41:50
  Probably ten minutes. I gotta get on Amazon
• 41:52
  Okay.
• 41:53
  and just be like, Gimme a new case. But
• 41:56
  Okay. I'll I'll often procrastinate on that for at least a couple months.
• 42:01
  I see your question. How long will it take? Well yeah, it it's been many
• 42:02
  months like this. Yeah, there's there's the procrastinator
• 42:04
  Right. there it is. There it is.
• 42:09
  in me. But that one's if the if it were a screen I was looking
• 42:14
  at different visual, my my brain would just shift to focusing on the the crack
• 42:20
  and not the work I'm I'm working on. So
• 42:24
  Got I love it. Okay. I got a rule. I think definitely scrappy, but there's
• 42:28
  a lot of sophistication in the actual world. I think I agree with your initial
• 42:32
  assessment. I think you have a foot in both worlds in both scrappy and sophisticated.
• 42:37
  Well, thank you for your insight and thanks for all this, Jack. Really. I we
• 42:41
  just met what a few weeks back, but I you know, we're I love what
• 42:46
  you're doing and I'm looking forward to a lot more connection. And I I I
• 42:51
  love what you're doing on the on the on the podcast here. I was I
• 42:56
  was thinking about
• 42:57
  I appreciate it
• 42:57
  going in. I was like, I've been thinking about for several years, like I want
• 43:00
  to do a podcast, but I just don't get to it and I don't get
• 43:04
  organized around it. And then I saw what you were doing, I'm like, Here's somebody
• 43:07
  who's got it figured out. And then I think
• 43:10
  Yeah.
• 43:11
  it's kind of like I I used to like to wash my own car, but
• 43:14
  and I just don't you know anymore because I just I don't enjoy washing the
• 43:18
  car. I used to love it. I worked in a car wash. I was like,
• 43:22
  I get to wash now, like I don't want to wash my car. And it
• 43:26
  and it's it's not that it it it it it it so anyway, when I
• 43:30
  saw what you were doing with podcast, I was like, some, you know. Connect you
• 43:34
  know, so I just love what you're doing with this. It's great work and thank
• 43:38
  you for having me on and do it all.
• 43:41
  Course. Thank you for coming on. I appreciate that. in the last kind of thirty
• 43:45
  seconds here, anything you want the folks out there to know, anything you want to
• 43:50
  promote.
• 43:51
  it my work with you is is really it. I that's I think we're I
• 43:55
  mean I'm I'm on LinkedIn. I mostly connect with people through my LinkedIn and and
• 44:00
  and go from there and often shift to email soon once we build the you
• 44:05
  know connection. but you know mm first and last name is pretty unique. I think
• 44:09
  there's one other person in the world
• 44:12
  Yeah.
• 44:13
  with the same last name and he must be related, but I don't know him.
• 44:19
  And and so I'm real easy to find. Google me. owlpoint dot net is the
• 44:25
  there's a few owl points out there, but dot net is me. And but yeah,
• 44:31
  just look forward to
• 44:33
  Awesome. Well, Mark, thank you so much for coming on. A foot in both worlds,
• 44:39
  scrappy and sophisticated. go check them out. Go check out owlpoint.net, everybody, and stay data
• 44:46
  driven, of course.