Think Like an Owner

My guest on this episode is Michael Coscetta. Michael has held several high-level sales roles at companies like Square, Compass, his own company, and his current role as CRO of Paxos, and through it all has become an expert in designing and managing sales teams.

This was a fantastic conversation about all things sales and building sales teams and is one I will be re-listening to several times over the coming years. While a large portion of Michael's time has been spent in very large sales organizations, the principles he talks about are still widely applicable in companies of any size, and all regular listeners to this podcast are in for a treat.

Michael and I talk about writing high-value sales contracts, the growing importance of high-performing sales operations, how sales have become data-driven and more quantitative, how to recruit for sales, and the leadership of sales.

One final note before the episode, I want to meet more sales professionals, especially in data and data software. If you, or someone you know, have expertise in data enterprise sales I would love the chance to connect. You can find me on my website alexbridgeman.com, LinkedIn, and Twitter, or send me an email directly at [email protected]. Thank you, I look forward to chatting soon!

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Links:

Paxos

Michael on LinkedIn

Superhuman's Fundraising Playbook with CEO Rahul Vohra on the Acquired Podcast

On Revenue Quality with Bradley Roofner and Logan Brown - Ep.145 of TLAO

Topics:

(4:32) - Michael's background and career

(7:03) - Are there any common principles you've picked up over the course of these vastly different experiences?

(9:28) - What have learned about building valuable sales contracts?

(12:42) - What processes or strategies have you developed to find the right pricing matrix arrangement?

(15:49) - Are there any questions you ask customers to find optimum pricing?

(18:55) - Have you seen an evolution in how sales teams are viewed in companies?

(22:04) - Is there any data set that has the most impact on a sales team?

(24:37) - What are the differences between sales orgs of less than 50 people and larger ones?

(27:33) - How do you go about setting sales goals?

(30:38) - Do you have a sense for trigger points for when you separate different parts of the sales process into their own individual teams

(32:42) - How do you view renewals or upsells for existing customers vs. new ones?

(33:57) - What personalities or characteristics work best for filling out different sales roles?

(40:31) - Are there any helpful questions or interview styles to determine whether a candidate is a good fit?

(42:57) - What are some best practices for making sure sales and products are communicating effectively?

(45:57) - Are there any communications methods that work well with customers?

(48:51) - How does the product team decide what customer feedback is valid and what is noise?

(53:09) - In this environment, how do you continue to build and improve your sales team?

(55:54) - Can you expand on the concept of the sales org being the brains of a revenue organization?

(58:00) - How can a CEO get more involved with their sales team in a non-disruptive way?

(1:00:16) - What strongly held belief have you changed your mind on?

(1:01:11) - What's the best business you've ever seen?

(1:04:06) - What other companies do you study and admire for their sales org?

My guest on this episode is Nick Buchanan. Nick and his father founded a data software business called BUCS Analytics in 2006. BUCS builds deep analytical dashboards for CEOs that pull from internal data sources like ERPs, inventory systems, and more. Long-time customer Trevor Flannigan, COO of the Flint Group, introduced us after hearing about my deep curiosity of data companies.

Nick and I talk about building the company with his father, building momentum in product development and sticking close to customers, hiring a talented team, and how to find groups and peers to help guide your entrepreneurial journey.

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Links:

Nick on LinkedIn

BUCS analytics

Sean Joy – CEO Journey within Chenmark – Ep.152

Timestamps

(00:00:00) Intro

(00:02:15) What is Bucs Analytics and the founding story?

(00:07:35) Are there any industries you've specialized in?

(00:09:38) Can you walk through product development?

(00:13:11) How do you decide on outcomes of experiments where results come out similar?

(00:16:25) Are there 2-3 ways you measure engagement and value?

(00:17:41) What's been the process of evolution on the sales side?

(00:20:53) What are the channels you're hoping to develop further?

(00:22:13) What are the benefits of having a group of peers over time?

(00:25:34) Is there one change or development in your peer group that's helped the most?

(00:27:35) Where was your mindset when starting Bucs and how has it changed over time?

(00:29:19) What are some of the most successful ways you've found to attract and keep talent at Bucs?

(00:32:21) What does it look like fulfilling a new employee's goals?

(00:34:46) What've you learned the most about managing change in a company?

(00:36:37) What's your philosophy for setting goals?

(00:39:21) Have you ever made secondary adjustments to annual goals?

(00:40:30) What goal do you feel you're the most excited to achieve this year?

(00:41:13) What strongly held belief have you changed your mind on?

(00:42:40) What's the best business you've ever seen?

My guest on this episode is Carl Streck, founder and CEO of MountainSeed, a data and software business serving commercial real estate professionals. I was introduced to Carl by Michael Arrieta after asking Michael for the most interesting entrepreneurs in data he knew of, and Carl's name was the first out of his mouth. Carl started MountainSeed in 2006 to build software serving banks making commercial real estate loans and eventually developed a data product to help banks make more data-driven decisions.

Carl and I talk about bootstrapping a data software company, evolutions in his management style as the company grew, the business models of data companies, and how staying close to customers impacted the development of their data product. Enjoy!

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Links:

Carl Streck on LinkedIn

MountainSeed

EOS

What Got You Here Won't Get You There by Marshall Goldsmith

YPO.org

The Economics of Data Businesses by Abraham Thomas

Craig Fuller on TLAO

Topics:

(2:46) - How has your thought process around raising capital changed over the years?

(5:43) - Does your mindset towards capital change when it comes to accelerating growth vs. starting growth?

(8:03) - What have you learned from peers or your own experience in finding the right investor/company fit?

(10:29) - What was your role and how did it evolve during different stages of team size in the organization?

(14:16) - As companies grow, where do you see CEOs and founders start to struggle?

(17:46) - Is there a way to build a culture that encourages feedback they might not want to share otherwise?

(21:05) - What are some of the most impactful behavioral changes you've made to build trust and feedback with the team?

(25:43) - When you study CEOs of larger companies, what is different about how they operate as leaders?

(28:23) - Can you walk us through how you view your product portfolio and how the two work together?

(32:40) -How do you compare SAAS businesses to Data Businesses?

(35:56) - Does your Data Analytics platform work within the platforms or software of customers?

(38:23) - How would you categorize the customers of your product?

(41:02) - Does the Analytics platform license 3rd party data sources?

(43:19) - How are you looking to design and build a data company that lasts?

(46:07) - How do you incorporate customer feedback or determine new features?

(49:09)- What's a strongly held belief you've changed your mind on?

(52:24) - What's the best business you've ever seen?

My guest on this episode is Sean Joy, CEO at Buccaneer Pirate and Southern Star Dolphin Cruise, a company owned by Chenmark in Destin, FL that provides seasonal boat tours. Sean was a part of Chenmark's GVP, the Generalist Vice President program that provides a career track to becoming a CEO at a Chenmark company.

Individuals start by working on a couple of projects within the portfolio, then take a non-CEO operating role in a company, before moving to a CEO role. Sean's background was in control workouts and restructuring, which we talk about to kick off the episode before he found a small business in Chenmark and inquired about their GVP program.

Over the course of the episode, we talk about Sean's finance experience, what he pays close attention to given his restructuring experience, managing cash in a highly seasonal business, the wide array of services offered on a tour boat and how they interact, and the power of price increases. Enjoy!

Listen weekly and follow the show on Apple Podcasts, Spotify, Google Podcasts, Stitcher, Breaker, and TuneIn.

Links:

Sean on LinkedIn

Southern Star Dolphin Cruise

Buccaneer Pirate Cruise

Chenmark

Topics:

(6:08) - What are some interesting lessons you learned and experiences in restructuring?

(12:52) - What are some habits you have today as a CEO that you can tie back to prior experiences in restructuring?

(14:40) - How did you connect with Chenmark and what about it was appealing to you?

(16:52) - What were the roles you had when you first joined the organization?

(20:27) - Were there any learning curves early on in your role as CEO?

(22:06) - How much debt was in the business?

(23:39) - What are some ways that you manage cash throughout the year with a heavily seasonal business?

(27:33) - What are some of the add-on services you've implemented to increase revenue?

(31:46) - What are your criteria for cutting vs. keeping products?

(32:47) - How much time and energy do you spend on pricing your products?

(38:10) - How dynamic is your pricing?

(39:28) - What other improvements are top of mind for you?

(46:26) - What strongly held belief have you changed your mind on?

(48:51) - What's the best business you've ever seen?

My guests on this episode are Heritage Holding co-founders Alex de Pfyffer and Ross Porter. Heritage acquires companies across industries, but has a special focus on IT services and data centers. I'm a data geek and love talking with entrepreneurs in data, and haven't talked with much of anyone on the hardware side so this conversation was a lot of fun for me.

We talk about identifying companies offering essential services, their data center acquisitions and strategy, what they've learned from private equity on growing companies, and thoughts on a long-term structure for Heritage going forward.

Listen weekly and follow the show on Apple Podcasts, Spotify, Google Podcasts, Stitcher, Breaker, and TuneIn.

Links:

Heritage Holding

Alex de Pfyffer on LinkedIn

Ross Porter on LinkedIn

Topics:

(3:03) - What's the background for Heritage and how did you each get to this point?

(5:56) - What ideas were you considering for a startup?

(7:57) - Have there been any guiding principals or common threads through the acquisitions you've done thus far?

(11:49) - What does the data center business model look like?

(13:53) - Is there some overlap with your ISP or Fiber investments?

(15:00) - Is there some first mover advantage to bring Fiber Optic Cable to a certain area?

(16:33) - Who is your typical competitor?

(18:38) - Once you own an ISP, what are the ROI metrics for expanding that footprint?

(20:27) - Where do you see other opportunities in data for investments?

(26:10) - What have you learned from managing companies of different sizes?

(34:09) - What changes the most when you go from $10m to $50m of EBITDA?

(37:29) - What are some structure questions in your mind as you look to future acquisitions?

(43:35) - What's a strongly held belief you've each changed your mind on?

(49:41) - What's the best business you've ever seen?

My guests on this episode are Johnny Lieberman and Zack Miller, who together founded Worklyn Partners to acquire and grow cybersecurity and IT services companies.

A concept we talk a lot about in the episode is how the two businesses create a flywheel between each other. I find these flywheels fascinating and I've talked about others such as the flywheel between media and data with FreightWaves founder Craig Fuller in Episode 121.

Johnny and Zack share how the two business models function both together and independently, where growth is coming from and trends driving that growth, developing sales teams, and why only the paranoid survive. Enjoy.

Listen weekly and follow the show on Apple Podcasts, Spotify, Google Podcasts, Stitcher, Breaker, and TuneIn.

Links:

Johnny Lieberman on LinkedIn

Zack Miller on LinkedIn

Worklyn Partners

Quadrant Information Security

Topics:

(2:41) - Can you walk us through the timeline of Worklyn and where you're at today?

(9:35) - How do your cybersecurity & IT platforms work collaboratively together?

(11:07) - Why are you pursuing growth via acquisition on the IT side but not in cybersecurity?

(17:07) - Is there a similar dynamic between sales in IT services and Cyber?

(18:08) - How does the sales cycle work from getting an IT customer over to the Cyber side?

(22:42) - What are some high-level industry tail winds you've observed?

(29:49) - Could the flywheel between Cyber and IT extend to software businesses or service tools that could support the business?

(33:59) - Within Worklyn, where do you see most of the value being created?

(36:49) - How have you been working to attract great people to your teams?

(40:01) - How have you structured management compensation?

My guest on this episode is Richard Reese. Richard took over as CEO of Iron Mountain, a physical records management business, in 1981. He ran the business as CEO through going public in 1996 before retiring from the role in 2013. Revenue over that period grew from around $3 million in 1981 to $3 billion in 2013.

Our discussion focuses on incentivizing teams with cash and stock, something Richard has thought deeply about over many decades, developing compensation plans, working with private and public investors, and a few stories from the early years of running Iron Mountain.

Listen weekly and follow the show on Apple Podcasts, Spotify, Google Podcasts, Stitcher, Breaker, and TuneIn.

Links:

Richard on LinkedIn

Iron Mountain

Topics:

(4:03) - Richard's background, career, and time as CEO for Iron Mountain

(14:03) - What became easier when you went public? What became harder?

(17:30) - What did your management team look like when you stepped in and how did you look to evolve it?

(24:29) - When you started thinking about incentivizing the management team, what were some ways you got them to buy in?

(38:35) - What kind of challenges did you run into with equity compensations?

My guest on this episode is Judd Lorson. Judd acquired Alliance CAS, a specialty collection agency, in 2018 as CEO and in 2021 resigned from the role after a much more difficult road and path than he'd anticipated. Judd's story was recently profiled in a Yale paper by A.J. Wasserstein titled "The Judd Lorson Story" which we will link to in the show notes and I highly recommend reading for background on Judd's time as CEO.

For this conversation, we are focusing on new daily habits and foundations he has created influenced by his experience, what he values today, how those values have changed over time and the power of having a growth mindset.

Listen weekly and follow the show on Apple Podcasts, Spotify, Google Podcasts, Stitcher, Breaker, and TuneIn.

Links:

"The Judd Lorson Story" by A.J. Wasserstein

The Slight Edge by Jeff Olson

Judd on LinkedIn

Contact Judd via email at [email protected]

Topics:

(4:10) - Judd's background and career

(14:44) - What was a typical day or week like for you as a CEO and what would that ideally look like today?

(21:10) - How do you feel now in your emotional balance now vs. when you were working in the business?

(23:07) - Do you think if you had started your work as CEO with these habits it would've been a more successful experience?

(24:42) - How are you planning to adjust your work-life balance in a potential second stint as CEO?

(28:13) - What advice would you give to young searchers who are in the process of making life changes outside of work such as starting a family?

(31:30) - What are some tactics you could use to engage with those changing dynamics over time?

(33:32) - What goals did you have for 2022?

(38:06) - What are some of your Slight Edge Habits?

(41:55) - Are you totally caffeine free?

(44:06) - Was there anything to simulate day and night while on the submarine?

(47:04) - What other changes in your daily habits or values are you looking to achieve in the future?

(50:04) - Is there a strongly held belief you've changed your mind on?

(53:12) - What's the best business you've ever seen?

My guest on this episode is Luis Reyes, managing partner at Iberian Ventures in Spain. Luis worked in strategy consulting before acquiring small companies in Spain in a similar vein as the search fund model through Iberian. We kick off by talking about the buyout market in Spain and what makes it particularly attractive. For example, all private companies in Spain have to file their financials with the government. As a result, the full financial picture of any company in Spain can be found and sorted.

We also spend a great deal of time talking about one of their core investment theses, the fire protection market, and why it's an ideal market for consolidation.

Listen weekly and follow the show on Apple Podcasts, Spotify, Google Podcasts, Stitcher, Breaker, and TuneIn.

Links:

Luis on LinkedIn

Iberian Ventures

Topics:

(3:42) - What is Spain like as a buyout market?

(9:05) - What are the regulations around requiring private companies to make their financials public?

(12:17) - Did you have any previous ties to Spain before deciding to plant roots there?

(13:52) - Was your previous career experience in finance and consulting helpful in working with business owners?

(15:12) - Can you give us a walkthrough of the companies you've purchased so far and how you structure acquisition?

(18:32) - What does the fire protection industry look like country-wide and how does it compare to how you've approached it?

(25:00) - What are financing options for acquisitions?

(26:33) - Can you walk us through an example of a transaction and integration?

(32:18) - What are your options for exiting?

(34:38) - What are the options or paths you're thinking about in the long-term?

(36:07) - Do you see other Searchers in Spain stepping outside the traditional model?

(38:09) - What other industries do you find interesting and is there any limit to your team's capabilities to manage over multiple industries?

(42:13) - Are you raising money to build internal software?

(45:25) - What's a strongly held belief you've changed your mind on?

My guests on this episode are Bradley Roofner and Logan Brown, who together, along with a third partner Kade Thomas, acquired WLE, a landscaping firm in Austin, Texas, in 2017. After nearly four years of operating, they sold the company to Brightview, a public landscaping company and one of the largest in the country.

Our discussion today focuses on revenue quality, a topic Bradley and Logan have given a great deal of thought to. We talk about defining revenue quality and how to identify high and low quality revenue, creating your ideal customer profile, how to sell that customer building a motivated sales organization, emphasizing high quality revenue across an organization, writing more valuable customer contracts, and various tips they have for CEOs looking to boost revenue quality and thereby their company's valuation. Enjoy.

Listen weekly and follow the show on Apple Podcasts, Spotify, Google Podcasts, Stitcher, Breaker, and TuneIn.

Links:

Bradley on LinkedIn

Logan on LinkedIn

The E-Myth by Michael Gerber

Topics:

(2:44) - What was the business you ran in Austin?

(4:29) - What would you say are some aspects of high-quality revenue and aspects of low-quality revenue?

(6:57) - Was there any revenue that wasn't as clear cut to be either high or low quality?

(8:35) - How did you beef up the quality of revenue in your first 90 days?

(15:350 - How did you go about determining who your ideal customer would be?

(19:38) - What decisions are made based on the ideal customer profile?

(28:09) - How did you build out your outside Sales Org?

(31:31) - Did you have more success hiring people for Sales that had industry experience or Sales experience?

(33:15) - How did you instruct Sales people to navigate price increases?

(35:01) - Was your Sales Team compensated based on margin?

(36:07) - What were some levers in cash and collections that improved Quality of Revenue?

(44:04) - Did you find that as Quality of Revenue increased, the number of customers in collections decreased?

(46:40) - Did you find some interaction between construction and maintenance?

(50:47) - How did you go about measuring the conversion rate from low to high quality revenue?

(53:11) - How did Quality of Revenue impact your lives?

(59:11) - What advice would you offer CEO's looking to do general clean up in their business?